2-(1H-indol-3-yl)ethan-1-amine [Tryptamine] by Asch

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126 substances in Reaxys

2016-06-21 14h:35m:59s (EST)

2 substances in Reaxys

2016-06-21 14h:38m:07s (EST)

NH 2

1. Query NH

Search as: As drawn, No mixtures, No charges, No radicals 2. Query

(1. Query) AND itemno in (2,1)

1/155

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Reaxys ID 125513 View in Reaxys

1/2 CAS Registry Number: 61-54-1 Chemical Name: tryptamine; 1H-indole-3-ethanamine; Tryptamine Linear Structure Formula: NC8H6CH2CH2NH2 Molecular Formula: C10H12N2 Molecular Weight: 160.219 Type of Substance: heterocyclic InChI Key: APJYDQYYACXCRM-UHFFFAOYSA-N Note:

NH 2

Substance Label (167) Label References 9

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Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys

Gnecco, Dino; Juarez, Jorge; Galindo, Alberto; Marazano, Christian; Enriquez, Raul G.; Synthetic Communications; vol. 29; nb. 2; (1999); p. 281 - 287, View in Reaxys; McKay, Matthew J.; Carroll, Anthony R.; Quinn, Ronald J.; Hooper, John N. A.; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 595 - 597, View in Reaxys; Pouilhes, Annie; Langlois, Yves; Chiaroni, Angele; Synlett; nb. 10; (2003); p. 1488 1490, View in Reaxys; Fisyuk; Mukanov; Chemistry of Heterocyclic Compounds; vol. 39; nb. 2; (2003); p. 277 - 279, View in Reaxys; Liu, Yanqin; Luo, Shengjun; Fu, Xingnian; Fang, Fang; Zhuang, Zeyang; Xiong, Wanting; Jia, Xueshun; Zhai, Hongbin; Organic Letters; vol. 8; nb. 1; (2006); p. 115 - 118, View in Reaxys; Tulyaganov; Chemistry of Natural Compounds; vol. 42; nb. 4; (2006); p. 459 - 461, View in Reaxys; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys; Marzorati, Mattia; Hult, Karl; Riva, Sergio; Danieli, Bruno; Advanced Synthesis and Catalysis; vol. 349; nb. 11-12; (2007); p. 1963 - 1968, View in Reaxys; Bremner, John B.; Sengpracha, Waya; Skelton, Brian W.; Synthetic Communications; vol. 38; nb. 12; (2008); p. 1931 -

8/155

2016-06-21 14:42:30

1939, View in Reaxys; Patent; THE UNIVERSITY OF BRITISH COLUMBIA; WO2008/52352; (2008); (A1) English, View in Reaxys; Carr, Gavin; Chung, Marco K. W.; Mauk, A. Grant; Andersen, Raymond J.; Journal of Medicinal Chemistry; vol. 51; nb. 9; (2008); p. 2634 - 2637, View in Reaxys; Patent; XUE, LIANG; Chan, William K.; Linnet, Stan W.; Linnet, Timothy N.; US2012/322816; (2012); (A1) English, View in Reaxys H-1

Patent; Gruenenthal GmbH; US2010/48554; (2010); (A1) English, View in Reaxys; Patent; Gruenenthal GmbH; US2012/29006; (2012); (A1) English, View in Reaxys

2a'

Concepcion Lozada; Soria-Arteche, Olivia; Teresa Ramirez Apan, Ma.; Nieto-Camacho, Antonio; Enriquez, Raul G.; Izquierdo, Teresa; Jimenez-Corona, Arturo; Bioorganic and Medicinal Chemistry; vol. 20; nb. 17; (2012); p. 5077 - 5084, View in Reaxys

Yang, Yi; Jiang, Xueliang; Qing, Feng-Ling; Journal of Organic Chemistry; vol. 77; nb. 17; (2012); p. 7538 - 7547, View in Reaxys

Kavala, Veerababurao; Janreddy, Donala; Raihan, Mustafa J.; Kuo, Chun-Wei; Ramesh, Chintakunta; Yao, Ching-Fa; Advanced Synthesis and Catalysis; vol. 354; nb. 11-12; (2012); p. 2229 - 2240, View in Reaxys

Arifuddin, M.; Lakshmikant, N.; Rajasekar, N.; Shinde, D. B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 51; nb. 8; (2012); p. 1168 - 1172,5, View in Reaxys

6{3}

Khoury, Kareem; Sinha, Mantosh K.; Nagashima, Tadamichi; Doemling, Alexander; Herdtweck, Eberhardt; Angewandte Chemie, International Edition; vol. 51; nb. 41; (2012); p. 10280 - 10283,4; Angewandte Chemie; vol. 124; nb. 41; (2012); p. 10426 - 10429, View in Reaxys; Khoury, Kareem; Sinha, Mantosh K.; Nagashima, Tadamichi; Herdtweck, Eberhardt; Doemling, Alexander; Angewandte Chemie - International Edition; vol. 51; nb. 41; (2012); p. 10280 - 10283; Angewandte Chemie; vol. 124; nb. 41; (2012); p. 10426 - 10429, View in Reaxys

Ind-1

Patent; GRUNENTHAL GmbH; US2010/9986; (2010); (A1) English, View in Reaxys

Patent; Universita Degli Studi Di Siena; US2009/238761; (2009); (A1) English, View in Reaxys

25; Compound 25 Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys; Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys TRY

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys

Ling, Ke-Qing; Li, Wen-Shan; Sayre, Lawrence M.; Journal of the American Chemical Society; vol. 130; nb. 3; (2008); p. 933 - 944, View in Reaxys

Table1,entry5,product

Bailey, Patrick D.; Beard, Mark A.; Dang, Hoa P.T.; Phillips, Theresa R.; Price, Richard A.; Whittaker, James H.; Tetrahedron Letters; vol. 49; nb. 13; (2008); p. 2150 - 2153, View in Reaxys

25a

Simila, Suvi T.M.; Martin, Stephen F.; Tetrahedron Letters; vol. 49; nb. 29-30; (2008); p. 4501 - 4504, View in Reaxys

2(5)

Werner; Turner; Chambers; Brummond; Tetrahedron; vol. 64; nb. 29; (2008); p. 6997 - 7007, View in Reaxys

Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 3865, View in Reaxys

amine

Alonso, Fernando; Acebedo, Sofia L.; Bruttomesso, Andrea C.; Ramirez, Javier A.; Steroids; vol. 73; nb. 12; (2008); p. 1270 - 1276, View in Reaxys

amine, d,m

Das, Biswanath; Kanth, Boddu Shashi; Majhi, Anjoy; Reddy, Kongara Ravinder; Heteroatom Chemistry; vol. 19; nb. 6; (2008); p. 630 - 633, View in Reaxys

Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys

amine/11

Chinni Mahesh; Narasimhulu; Srikanth Reddy; Suryakiran; Venkateswarlu; Tetrahedron Letters; vol. 48; nb. 1; (2007); p. 55 - 59, View in Reaxys

Rose, Mickea D.; Cassidy, Michael P.; Rashatasakhon, Paitoon; Padwa, Albert; Journal of Organic Chemistry; vol. 72; nb. 2; (2007); p. 538 - 549, View in Reaxys

Sarang, Prajakta S.; Yadav, Arun A.; Patil, Prashant S.; Krishna, Urlam Murali; Trivedi, Girish K.; Salunkhe, Manikrao M.; Synthesis; nb. 7; (2007); p. 1091 - 1095, View in Reaxys

Androsov, Dmitry A.; Neckers, Douglas C.; Journal of Organic Chemistry; vol. 72; nb. 14; (2007); p. 5368 5373, View in Reaxys

9/155

2016-06-21 14:42:30

TRA

Carney, Joel R.; Zwier, Timothy S.; Chemical Physics Letters; vol. 341; nb. 1-2; (2001); p. 77 - 85, View in Reaxys; Carney; Dian; Florio; Zwier; Journal of the American Chemical Society; vol. 123; nb. 23; (2001); p. 5596 - 5597, View in Reaxys; Caminati, Walther; Physical Chemistry Chemical Physics; vol. 6; nb. 10; (2004); p. 2806 - 2809, View in Reaxys; Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys; LeGreve, Tracy A.; Baquero, Esteban E.; Zwier, Timothy S.; Journal of the American Chemical Society; vol. 129; nb. 13; (2007); p. 4028 - 4038, View in Reaxys; Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys

educt to 3j

Willand, Nicolas; Folleas, Benoit; Boutillon, Christophe; Verbraeken, Liesbeth; Gesquiere, JeanClaude; Tartar, Andre; Deprez, Benoit; Tetrahedron Letters; vol. 48; nb. 29; (2007); p. 5007 - 5011, View in Reaxys

NH2CH2CH2Ind

Kamoune, Laila; De Borggraeve, Wim M.; Gielens, Constant; Voet, Arnout; Robeyns, Koen; De Maeyer, Marc; Van Meervelt, Luc; Compernolle, Frans; Hoornaert, Georges; European Journal of Organic Chemistry; nb. 18; (2007); p. 2977 - 2986, View in Reaxys

Shinkre, Bidhan A.; Raisch, Kevin P.; Fan, Liming; Velu, Sadanandan E.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 10; (2007); p. 2890 - 2893, View in Reaxys

educt to 2f

Pereira, Maria de Fatima; Thiery, Valerie; Besson, Thierry; Tetrahedron Letters; vol. 48; nb. 43; (2007); p. 7657 - 7659, View in Reaxys

IIa

Shestakov; Sidorenko; Shikhaliev; Pavlenko; Russian Journal of General Chemistry; vol. 77; nb. 10; (2007); p. 1749 - 1760, View in Reaxys

Table 4, entry 9, amine

Hollmann, Dirk; Baehn, Sebastian; Tillack, Annegret; Beller, Matthias; Angewandte Chemie - International Edition; vol. 46; nb. 43; (2007); p. 8291 - 8294, View in Reaxys

I-4a

Ates-Alagoz, Zeynep; Coban, Tulay; Buyukbingol, Erdem; Archiv der Pharmazie; vol. 339; nb. 4; (2006); p. 193 - 200, View in Reaxys

29d

Zhu, Guangyu; Yang, Fanglong; Balachandran, Raghavan; Hoeoek, Peter; Vallee, Richard B.; Curran, Dennis P.; Day, Billy W.; Journal of Medicinal Chemistry; vol. 49; nb. 6; (2006); p. 2063 - 2076, View in Reaxys

24, R4=3-indolyl(CH2)2

Doncaster, Jeremy R.; Etchells, Laura L.; Kershaw, Neil M.; Nakamura, Ryoichi; Ryan, Hazel; Takeuchi, Ryo; Sakaguchi, Kengo; Sardarian, Ali; Whitehead, Roger C.; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 11; (2006); p. 2877 - 2881, View in Reaxys

VIIa

Fisyuk; Mukanov; Russian Journal of Organic Chemistry; vol. 42; nb. 9; (2006); p. 1269 - 1274, View in Reaxys

Am5

Chung, Yun Mi; Raman, Balamurali; Ahn, Kyo Han; Tetrahedron; vol. 62; nb. 50; (2006); p. 11645 - 11651, View in Reaxys

R2-C

Habashita, Hiromu; Kokubo, Masaya; Hamano, Shin-Ichi; Hamanaka, Nobuyuki; Toda, Masaaki; Shibayama, Shiro; Tada, Hideaki; Sagawa, Kenji; Fukushima, Daikichi; Maeda, Kenji; Mitsuya, Hiroaki; Journal of Medicinal Chemistry; vol. 49; nb. 14; (2006); p. 4140 - 4152, View in Reaxys; Habashita, Hiromu; Kokubo, Masaya; Hamano, Shin-ichi; Hamanaka, Nobuyuki; Toda, Masaaki; Shibayama, Shiro; Tada, Hideaki; Sagawa, Kenji; Fukushima, Daikichi; Maeda, Kenji; Mitsuya, Hiroaki; J. Med. Chem.; vol. 49; nb. 14; (2006); p. 4145 - 4152, View in Reaxys

Das, Biswanath; Venkateswarlu, Katta; Krishnaiah, Maddeboina; Holla, Harish; Tetrahedron Letters; vol. 47; nb. 43; (2006); p. 7551 - 7556, View in Reaxys

Haak, Edgar; Synlett; nb. 12; (2006); p. 1847 - 1848, View in Reaxys

McCoy, Elizabeth; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 128; nb. 44; (2006); p. 14276 - 14277, View in Reaxys

tam

Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.; Phytochemistry; vol. 67; nb. 6; (2006); p. 561 - 569, View in Reaxys

Burkoth, Timothy S.; Fafarman, Aaron T.; Charych, Deborah H.; Connolly, Michael D.; Zuckermann, Ronald N.; Journal of the American Chemical Society; vol. 125; nb. 29; (2003); p. 8841 - 8845, View in Reaxys; Shen, Ya-Ching; Chen, Ching-Yeu; Hsieh, Pei-Wen; Duh, Chang-Yih; Lin, Yat-Min; Ko, Chin-Lien; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 1; (2005); p. 32 - 36, View in Reaxys

Pradhan, Prasun K.; Dey, Sumit; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 35; nb. 7; (2005); p. 913 - 922, View in Reaxys

III-4a

Gurkan, A. Selen; Karabay, Arzu; Buyukbingol, Zeliha; Adejare, Adeboye; Buyukbingol, Erdem; Archiv der Pharmazie; vol. 338; nb. 2-3; (2005); p. 67 - 73, View in Reaxys

10/155

2016-06-21 14:42:30

amine f

Kuhnert, Nikolai; Le-Gresley, Adam; Tetrahedron Letters; vol. 46; nb. 12; (2005); p. 2059 - 2062, View in Reaxys

Rosamilia, Anthony E.; Scott, Janet L.; Strauss, Christopher R.; Organic Letters; vol. 7; nb. 8; (2005); p. 1525 - 1528, View in Reaxys

Feldman, Ken S.; Vidulova, Daniela Boneva; Karatjas, Andrew G.; Journal of Organic Chemistry; vol. 70; nb. 16; (2005); p. 6429 - 6440, View in Reaxys

amine, T.1, e.4

Yan, Ri-Bai; Yang, Fan; Wu, Yanfen; Zhang, Li-He; Ye, Xin-Shan; Tetrahedron Letters; vol. 46; nb. 52; (2005); p. 8993 - 8995, View in Reaxys

substrate to 6

Ho, Tse-Lok; Chen, Chun-Kuei; Helvetica Chimica Acta; vol. 88; nb. 10; (2005); p. 2764 - 2770, View in Reaxys

8<12>

Wipf, Peter; Werner, Stefan; Woo, Grace H.C.; Stephenson, Corey R.J.; Walczak, Maciej A.A.; Coleman, Claire M.; Twining, Leslie A.; Tetrahedron; vol. 61; nb. 48; (2005); p. 11488 - 11500, View in Reaxys

educt to 7-11

Li, Donghong; Zhang, Yongbin; Guo, Wei; Xia, Chizhong; Heterocycles; vol. 65; nb. 5; (2005); p. 1063 1069, View in Reaxys

Karpov, Alexei S.; Rominger, Frank; Mueller, Thomas J. J.; Organic and Biomolecular Chemistry; vol. 3; nb. 24; (2005); p. 4382 - 4391, View in Reaxys

Feldman, Ken S.; Vidulova, Daniela Boneva; Organic Letters; vol. 6; nb. 11; (2004); p. 1869 - 1871, View in Reaxys; Patent; SEQUELLA, INC.; WO2005/34857; (2005); (A2) English, View in Reaxys

start to 5,6

Voskressensky, Leonid G.; Borisova, Tatiana N.; Kulikova, Larisa N.; Varlamov, Alexej V.; Catto, Marco; Altomare, Cosimo; Carotti, Angelo; European Journal of Organic Chemistry; nb. 14; (2004); p. 3128 3135, View in Reaxys

Mortoni, Annalisa; Martinelli, Marisa; Piarulli, Umberto; Regalia, Nickolas; Gagliardi, Stefania; Tetrahedron Letters; vol. 45; nb. 35; (2004); p. 6623 - 6627, View in Reaxys

Sawa, Masaaki; Tateishi, Hirotaka; Mizuno, Kazuhiro; Harada, Hiroshi; Oue, Mayumi; Tsujiuchi, Hiroshi; Furutani, Yasuji; Kato, Shiro; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 24; (2004); p. 5963 - 5966, View in Reaxys

Tab. 1, entry 1, amine

Andrade, Carlos Kleber Z.; Takada, Sayuri Cristina S.; Magalhaes Alves, Luana; Petrocchi Rodrigues, Juliana; Suarez, Paulo Anselmo Z.; Brandao, Rodrigo Fleury; Soares, Valerio Cassiano D.; Synlett; nb. 12; (2004); p. 2135 - 2138, View in Reaxys

IIId

Mironov; Tokareva; Ivantsova; Mokrushin; Russian Journal of Organic Chemistry; vol. 40; nb. 6; (2004); p. 847 - 853, View in Reaxys

amine 5

Bashford, Katherine E.; Burton, Matthew B.; Cameron, Stuart; Cooper, Anthony L.; Hogg, Rebecca D.; Kane, Peter D.; MacManus, David A.; Matrunola, Christopher A.; Moody, Christopher J.; Robertson, Avril A. B.; Warne, Mark R.; Tetrahedron Letters; vol. 44; nb. 8; (2003); p. 1627 - 1629, View in Reaxys

sch1, amine/d

Zhu, Xiaoxiang; Yu, Qian-sheng; Greig, Nigel H.; Flippen-Anderson, Judith L.; Brossi, Arnold; Heterocycles; vol. 59; nb. 1; (2003); p. 115 - 128, View in Reaxys

6(n-5)

Giacomelli, Giampaolo; Porcheddu, Andrea; Salaris, Margherita; Taddei, Maurizio; European Journal of Organic Chemistry; nb. 3; (2003); p. 537 - 541, View in Reaxys

amine run 9-12

Zhang, Wei; Chen, Christine Hiu-Tung; Nagashima, Tadamichi; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2065 - 2068, View in Reaxys

22 (tab3 run3)

Nagle, Advait S.; Salvatore, Ralph N.; Cross, Richard M.; Kapxhiu, Elona A.; Sahab, Suma; Yoon, Cheol Hwan; Jung, Kyung Woon; Tetrahedron Letters; vol. 44; nb. 30; (2003); p. 5695 - 5698, View in Reaxys

5<3>

Chen, Christine Hiu-Tung; Zhang, Wei; Organic Letters; vol. 5; nb. 7; (2003); p. 1015 - 1017, View in Reaxys

Educt, Tab.1, run 7

Gaj, Xinjie; Grigg, Ronald; Khamnaen, Tossapol; Rajviroongit, Shuleewan; Sridharan, Visuvanathar; Zhang, Lixin; Collard, Simon; Keep, Ann; Tetrahedron Letters; vol. 44; nb. 40; (2003); p. 7441 - 7444, View in Reaxys

to 5 n=1,2 Table 1 Abelman, Matthew M.; Curtis, Jeffrey K.; James, Donald R.; Tetrahedron Letters; vol. 44; nb. 34; (2003); p. 6527 - 6531, View in Reaxys 4f

Karpov, Alexei S.; Mueller, Thomas J. J.; Synthesis; nb. 18; (2003); p. 2815 - 2826, View in Reaxys

Indole-3CH2CH2-NH2

Henkel, Bernd; Westner, Benedikt; Doemling, Alexander; Synlett; nb. 15; (2003); p. 2410 - 2412, View in Reaxys

11/155

2016-06-21 14:42:30

5, R = H

Jiang, Weiqin; Zhang, Xuqing; Sui, Zhihua; Organic letters; vol. 5; nb. 1; (2003); p. 43 - 46, View in Reaxys

Box, Karl; Bevan, Christopher; Comer, John; Hill, Alan; Allen, Ruth; Reynolds, Derek; Analytical Chemistry; vol. 75; nb. 4; (2003); p. 883 - 892, View in Reaxys

scheme 6

Marchetti; Botteghi; Paganelli; Taddei; Advanced Synthesis and Catalysis; vol. 345; nb. 11; (2003); p. 1229 - 1236, View in Reaxys

educt to 6a

Brown, Richard T.; Dauda, Bukar E.N.; Pratt, Simon B.; Richards, Paul; Heterocycles; vol. 56; nb. 1-2; (2002); p. 51 - 58, View in Reaxys

Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys

educt to III.263

Fernandez; Garcia-Ochoa; Huss; Mallo; Bueno; Micheli; Paio; Piga; Zarantonello; Tetrahedron Letters; vol. 43; nb. 27; (2002); p. 4741 - 4745, View in Reaxys

Substr., Tab.1, run 1-4

Connors, Richard V.; Zhang, Alex J.; Shuttleworth, Stephen J.; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6661 - 6663, View in Reaxys

Nicewonger, Robert B; Ditto, Lori; Kerr, Doug; Varady, Laszlo; Bioorganic and medicinal chemistry letters; vol. 12; nb. 14; (2002); p. 1799 - 1802, View in Reaxys

educt to 8

Wasserman, Harry H.; Long, Yun Oliver; Zhang, Rui; Parr, Jonathan; Heterocycles; vol. 58; (2002); p. 393 - 403, View in Reaxys

triptamin-NH2

Chang, Meng-Yang; Chen, Shui-Tein; Chang, Nein-Chen; Heterocycles; vol. 57; nb. 12; (2002); p. 2321 2334, View in Reaxys

tryptyl-NH2

Rodenko, Boris; Wanner, Martin J.; Koomen, Gerrit-Jan; Journal of the Chemical Society. Perkin Transactions 1; nb. 10; (2002); p. 1247 - 1252, View in Reaxys

Tryp

Wee; Yu; Journal of Organic Chemistry; vol. 66; nb. 26; (2001); p. 8935 - 8943, View in Reaxys; Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys

R1R2NH (entry m)

Marcotte, Felix-Antoine; Lubell, William D.; Organic Letters; vol. 4; nb. 15; (2002); p. 2601 - 2603, View in Reaxys

educt, Tab. 1, run 7

Eguchi, Masakatsu; Lee, Min S.; Stasiak, Marcin; Kahn, Michael; Tetrahedron Letters; vol. 42; nb. 7; (2001); p. 1237 - 1239, View in Reaxys

3-Indolyl(CH2)2NH2

McLay, Iain M.; Halley, Frank; Souness, John E.; McKenna, Jeffrey; Benning, Veronique; Birrell, Mark; Burton, Brenda; Belvisi, Maria; Collis, Alan; Constan, Alex; Foster, Martyn; Hele, David; Jayyosi, Zaid; Kelley, Mike; Maslen, Chris; Miller, Glen; Ouldelhkim, Marie-Claude; Page, Kenneth; Phipps, Simon; Pollock, Kenneth; Porter, Barry; Ratcliffe, Andrew J.; Redford, Elisabeth J.; Webber, Stephen; Slater, Bryan; Thybaud, Veronique; Wilsher, Nicola; Bioorganic and Medicinal Chemistry; vol. 9; nb. 2; (2001); p. 537 - 554, View in Reaxys

Chu, Lin; Hutchins, Jennifer E.; Weber, Ann E.; Lo, Jane-Ling; Yang, Yi-Tien; Cheng, Kang; Smith, Roy G.; Fisher, Michael H.; Wyvratt, Matthew J.; Goulet, Mark T.; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 4; (2001); p. 509 - 513, View in Reaxys

Stefane, Bogdan; Ernigoj, Urh; Kocevar, Marijan; Polanc, Slovenko; Tetrahedron Letters; vol. 42; nb. 38; (2001); p. 6659 - 6662, View in Reaxys

Somei; Yamada; Kurauchi; Nagahama; Hasegawa; Teranishi; Sato; Kaneko; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 1; (2001); p. 87 - 96, View in Reaxys

educt to 11

Magnus, Philip; Gazzard, Lewis; Hobson, Lindsay; Payne, Andrew H.; Lynch, Vince; Tetrahedron Letters; vol. 40; nb. 28; (1999); p. 5135 - 5138, View in Reaxys; Zhang, Jing-Xin; Wang, Guang-Xing; Xie, Ping; Chen, Shu-Feng; Liang, Xiao-Tian; Tetrahedron Letters; vol. 41; nb. 13; (2000); p. 2211 - 2213, View in Reaxys

Merck 9927

Van Hooft, Johannes A.; Vijverberg, Henk P.M.; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 839 - 846, View in Reaxys; Miyafuji, Akio; Ito, Katsuji; Katsuki, Tsutomu; Heterocycles; vol. 52; nb. 1; (2000); p. 261 - 272, View in Reaxys

educt to 10

Wee, Andrew G.H.; Yu, Qing; Tetrahedron Letters; vol. 41; nb. 5; (2000); p. 587 - 590, View in Reaxys

NH2-β-(3-indolyl)ethyl

Heaney, Harry; Taha, Mutasem O.; Tetrahedron Letters; vol. 41; nb. 12; (2000); p. 1993 - 1996, View in Reaxys

Barrett, Anthony G. M.; Cramp, Susan M.; Roberts, Richard S.; Zecri, Frederic J.; Organic Letters; vol. 2; nb. 3; (2000); p. 261 - 264, View in Reaxys

12/155

2016-06-21 14:42:30

educt to 6

Bagley; Hind; Moody; Tetrahedron Letters; vol. 41; nb. 35; (2000); p. 6897 - 6900, View in Reaxys

Bubnov, Yury N.; Zhun', Ilya V.; Klimkina, Elena V.; Ignatenko, Anatoly V.; Starikova, Zoya A.; European Journal of Organic Chemistry; nb. 19; (2000); p. 3323 - 3327, View in Reaxys

Spychala, Jaroslaw; Tetrahedron; vol. 56; nb. 40; (2000); p. 7981 - 7986, View in Reaxys

Tab.4., run 8, amine

Chung, In Hwa; Cha, Ki Suk; Seo, Jae Hong; Kim, Joong Hyup; Chung, Bong Young; Kim, Choong Sup; Heterocycles; vol. 53; nb. 3; (2000); p. 529 - 533, View in Reaxys

educt to 13

Karoyan, Philippe; Triolo, Antonio; Nannicini, Rossano; Giannotti, Danilo; Altamura, Maria; Chassaing, Gerard; Perrotta, Enzo; Tetrahedron Letters; vol. 40; nb. 1; (1999); p. 71 - 74, View in Reaxys

precursor of 10 and 11

Koike, Kazuo; Yoshino, Hiroshi; Nikaido, Tamotsu; Heterocycles; vol. 51; nb. 2; (1999); p. 315 - 323, View in Reaxys

Amine, Tab. 1/2,run3/4-5

Bussolari; Rehborn; Combs; Tetrahedron Letters; vol. 40; nb. 7; (1999); p. 1241 - 1244, View in Reaxys

educt to 23a

Mehta, Goverdhan; Reddy, D. Srinivasa; Tetrahedron Letters; vol. 40; nb. 5; (1999); p. 991 - 994, View in Reaxys

RNH2, R=2-(3-indolyl)Et

Filigheddu, Silvia N.; Masala, Simonetta; Taddei, Maurizio; Tetrahedron Letters; vol. 40; nb. 35; (1999); p. 6503 - 6506, View in Reaxys

educt to 2

Boumendjel, Ahcene; Nuzillard, Jean-Marc; Massiot, Georges; Tetrahedron Letters; vol. 40; nb. 51; (1999); p. 9033 - 9036, View in Reaxys

2. educt to 4

Ducrot, Pierre; Thal, Claude; Tetrahedron Letters; vol. 40; nb. 51; (1999); p. 9037 - 9040, View in Reaxys

1, TA

Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys

Spadoni, Gilberto; Balsamini, Cesarino; Bedini, Annalida; Carey, Aedin; Diamantini, Giuseppe; Di Giacomo, Barbara; Tontini, Andrea; Tarzia, Giorgio; Nonno, Romolo; Lucini, Valeria; Pannacci, Marilou; Michaylov Stankov, Bojidar; Fraschini, Franco; Medicinal Chemistry Research; vol. 8; nb. 9; (1998); p. 487 - 498, View in Reaxys

Guardado, Pilar; Balon, Manuel; Carmona, Carmen; Munoz, Maria A.; Domene, Carmen; Journal of Pharmaceutical Sciences; vol. 86; nb. 1; (1997); p. 106 - 109, View in Reaxys

peak P18

Williamson, Brian L.; Benson, Linda M.; Tomlinson, Andy J.; Mayeno, Arthur N.; Gleich, Gerald J.; Naylor, Stephen; Toxicology Letters; vol. 92; nb. 2; (1997); p. 139 - 148, View in Reaxys

Patent-Specific Data (18) Prophetic ComLocation in Patent References pound Page/Page column

Patent; INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES; Shi, Jiangong; Zhang, Jianjun; Yue, Zhenggang; Li, Min; Zhu, Chenggen; Zhang, Ying; Zi, Jiachen; Wang, Yafang; Fan, Xiaona; Xu, Ruiming; Lin, Sheng; Li, Yan; Yang, Yongchun; Sheng, Li; US2013/45942; (2013); (A1) English, View in Reaxys; Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); (A1) English, View in Reaxys Patent; NEUROPORE THERAPIES, INC.; STOCKING, Emily, M.; WRASIDLO, Wolfgang; WO2015/116663; (2015); (A1) English, View in Reaxys Patent; Nippon Zoki Pharmaceutical Co., Ltd.; OOKUBO, Tomohiro; NAKAMURA, Ko; NAKAZAWA, Yoshitaka; NANBA, Hiroyoshi; YOSHIDA, Hiroyuki; EP2940003; (2015); (A1) English, View in Reaxys Patent; CHEMILIA AB; HOeGBERG, Marita; DAHLSTEDT, Emma; SMITT, Olof; JOHANSSON, Tommy; WO2012/127032; (2012); (A1) English, View in Reaxys Patent; GRUNENTHAL GmbH; US2010/9986; (2010); (A1) English, View in Reaxys Patent; ACURE PHARMA AB; US2010/98629; (2010); (A1) English, View in Reaxys

prophetic product

Claim

Patent; Saurat, Jean Hilaire; US2010/324109; (2010); (A1) English, View in Reaxys Patent; Gruenenthal GmbH; US2009/111842; (2009); (A1) English, View in Reaxys

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Patent; Banner, David; Hilpert, Hans; Kuhn, Bernd; Mauser, Harald; US2007/129421; (2007); (A1) English, View in Reaxys Patent; Fourtillan, Jean-Bernard; Fourtillan, Marianne; Karam, Omar; Zunino, Fabien; Jacquesy, Jean-Claude; Tafani, Jean-Pierre; US2006/89372; (2006); (A1) English, View in Reaxys Patent; WYETH; WO2006/124875; (2006); (A2) English, View in Reaxys Patent; GRUeNENTHAL GMBH; WO2005/66183; (2005); (A1) German, View in Reaxys Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/63186; (2004); (A1) English, View in Reaxys Patent; GRUeNENTHAL GMBH; WO2004/43967; (2004); (A1) German, View in Reaxys prophetic product

Patent; Schmitz, Robert A.; US6299892; (2001); (B1) English, View in Reaxys; Patent; ISIS Pharmaceuticals, Inc.; US6828427; (2004); (B1) English, View in Reaxys Patent; GRUeNENTHAL GMBH; WO2004/43899; (2004); (A1) German, View in Reaxys Patent; Pfizer Inc.; US2004/192698; (2004); (A1) English, View in Reaxys Patent; Aventis Pharma Limited; US6352977; (2002); (B1) English, View in Reaxys

Related Structure (3) Related Structure References The author inves- Philips, Laura A.; Levy, Donald H.; Journal of Physical Chemistry; vol. 90; nb. 21; (1986); p. 4921 - 4923, tigated the config- View in Reaxys uration In der frueher (s. E I 22 636) unter dieser Konstitution beschriebenen Verbindung (F: 145-146grad) hat wahrscheinlich <2-Indol-3-ylaethyl>-isopropyliden-amin vorgelegen.

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys Derivative (49) Comment (Derivative)

Derivative

By formation of salt/complex with TFA; Additional data: 1H NMR, shifts, D2O, 400 MHz, 15 deg C; 13C NMR, shifts, D2O, 126 MHz, 15 deg C

References Maresh, Justin J.; Giddings, Lesley-Ann; Friedrich, Anne; Loris, Elke A.; Panjikar, Santosh; Trout, Bernhardt L.; Stoeckigt, Joachim; Peters, Baron; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 130; nb. 2; (2008); p. 710 - 723, View in Reaxys

tryptamine hydochloride

Biswas, Kshetra M.; Jackson, Anthony H.; Kobaisy, Mozaina M.; Shannon, Patrick V. R.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1992); p. 461 - 468, View in Reaxys; Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys

TMS-Der.: MS

Raeisaenen; Kaerkkaeinen; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 33; (1979); p. 11, View in Reaxys

Protoniertes Kation = HTam+: ODMR-Frequenzen (S.7142); Rk. m. CH3HgOH: Gleichgew.-konst. (S.7140)

Svejda et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 7138, View in Reaxys

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Hydrochlorid: F: 248-249grad

Kametani et al.; Synthesis; (1972); p. 475, View in Reaxys; Patent; Nikhon kemifa h.h; JP5230513; (1977); Ref. Zh., Khim.; vol. 15; nb. O150P; (1978), View in Reaxys

Hydrochlorid: F: 240grad; IR

Patent; Buzas; Lavielle; FR2338259; (1977); Chem.Abstr.; vol. 88; nb. 120984, View in Reaxys

Hydrochlorid: FDMS (Tab. III)

Wood et al.; Analytical Chemistry; vol. 48; (1976); p. 981, View in Reaxys

Hydrochlorid

Okubo et al.; Journal of Physical Chemistry; vol. 79; (1975); p. 2108,2109, View in Reaxys

Komplex m. NATH: Ass.Konst. (Tab. I)

Okubo et al.; Journal of Physical Chemistry; vol. 79; (1975); p. 2108,2109, View in Reaxys

Hydrochlorid: F: 248-250grad

Suvorov et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1316,1320; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1496, View in Reaxys

Pikrat: F: 247-248grad

Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys

Tartrat: F: 182-183grad

Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys

Hydrochlorid: Konform.; Atomabstaende, Bindungswinkel; Kristallstruktur; F: 256-257grad; D=1.261

Wakahara et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 2481,2482-2486, View in Reaxys

Hydrochlorid: Diff.-Sp. in W.

Andrews; Forster; Biochemistry; vol. 11; nb. 10; (1972); p. 1875 - 1879, View in Reaxys

3,5-Dinitro-benzoyl-Derivat: Rk. m. Na-ethylat, NaOH, Acn.: Abs.-Sp. d. Reaktionsprodukts

Obtemperanskaya; Likhosherstova; J. Anal. Chem. USSR (Engl. Transl.); vol. 26; (1971); p. 158,140, View in Reaxys

(2,4-Dinitro-benzoyl)-Acn.-Komplex: Abs.

Obtemperanskaya et al.; J. Anal. Chem. USSR (Engl. Transl.); vol. 25; (1970); p. 2033,1744, View in Reaxys

Hydrochlorid C10H12N2*HCl: F: 244.5-245.5grad

Avramenko et al.; Pharmaceutical Chemistry Journal; nb. 12; (1970); p. 671; KhimikoFarmatsevticheskii Zhurnal; nb. 12; (1970); p. 10, View in Reaxys

Hydrochlorid: Loeschung d. Riboflavin-Phosphat-Fluoreszenz, Kinetik

Bowd et al.; Photochemistry and Photobiology; vol. 11; (1970); p. 445,447, View in Reaxys

Hydrochlorid: F: 256-257grad; ρ=1.261 g/cm3; Roentgenstruktur; H-Bruecken; Molekuelpackung

Wakahara; Fujiwara; Tomita; Tetrahedron letters; vol. 57; (1970); p. 4999 - 5002, View in Reaxys

<C10H13N2> +<C25H23Br2O5 S>-: Prep.: Ionenpaarextraktion m. CH2Cl2 (Bromthymolblau); logE(HAHY), -

Borg et al.; Journal of Pharmacy and Pharmacology; vol. 22; (1970); p. 507,508,509, View in Reaxys

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logk(d(A))*k'(HAT) ; Produktverteilung logD(HAHY) Hydrochlorid: ε(630)

Kitaoka; Nakano; Journal of Biochemistry (Tokyo, Japan); vol. 66; (1969); p. 87,91, View in Reaxys

Hydrochlorid: Rk. m. Secologanin (Phosphatpuffer, pH 4.5) fuehrt zu Vincosid- u. Isovincosid-hydrochlorid

Battersby,A.R. et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 1193 - 1200, View in Reaxys

Hydrochlorid v. <1'-14C>-Tryptamin: Rk. m. 1.) Tosylchlorid, 2.) <14C>-Methyliodid, 3.) Na, fl. NH3 fuehrt zu <N(ω)-14C>Methyl-<1'-14C>tryptamin

Gross et al.; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 9; nb. 2; (1969); p. 64, View in Reaxys

Hydrochlorid: Rk. m. Secologanin (Phosphatpuffer, pH 6.2) fuehrt zu 2-(2-cis-β-D-Glucopyranosyloxy-3-vinyl-5-methoxycarbonyl-3ref,4-cis-Dihydro-2H-pyranyl-4methyl)-spiro(pyrrolidin-....

Battersby,A.R. et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 1193 - 1200, View in Reaxys

Hydrochlorid: F: 256grad

Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys

Charge-TransferBanden m. Trinitrobenzol (S.210)

Millie et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 207,209,210, View in Reaxys

Charge-TransferBanden m. Tetracyanethylen (S. 210)

Millie et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 207,209,210, View in Reaxys

Pikrat: F: 240242grad (Zers.)

Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys

Hydrochlorid: F: 251-253grad

Pfeil,E.; Harder,U.; Angewandte Chemie; vol. 79; (1967); p. 188, View in Reaxys

Hydrochlorid: Rk. m. Pivaloylchlorid fuehrt zu N(β)Pivaloyltryptamin; Rk. m. Diphenylacetylchlorid fuehrt zu N(β)-Diphenylacetyltryptamin

Eichele; Mutschler; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 300; nb. 12; (1967); p. 1038, View in Reaxys

Flavinmononucleotid-Komplex: ΔF; ΔH; ΔS; Abs.Sp. (Tab. 1); Assoziationskonst.

Wilson; Biochemistry; vol. 5; (1966); p. 1351,1355, View in Reaxys

Hydrochlorid: F: 252.5-254.5grad

Brubacher,L.J.; Bender,M.L.; Journal of the American Chemical Society; vol. 88; (1966); p. 5871 - 5880, View in Reaxys

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(Zers.); pK(a); Rk. m. trans-Cinnamoyl-Papain (Kinetik): Geschw.konst. Pikrat C10H12N2*C6H3 N3O7: F: 243grad (Zers.)

Tacconi; Farmaco, Edizione Scientifica; vol. 20; (1965); p. 891,895,899, View in Reaxys

Hydrochlorid: Inhibitions-Konstante f. Acetylcholinesterase

Krupka; Biochemistry; vol. 4; (1965); p. 429,431, View in Reaxys

Hydrochlorid 2d: Prep.: N-Isopropyliden-tryptamin, HCl; F: 248grad (A.-E.)

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys

Pikrat 2e: Prep.: N-Isopropylidentryptamin, Pikrinsaeure; F: 244grad (?) (A.), (242grad); rot

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys

Sulfat: Rk. m. Vanillin in verd. wss. H2SO4 fuehrt zu 1-(4-Hydroxy-3methoxy-phenyl)-1,2,3,4-tetrahydro-β-carbolin; Rk. m. Benzaldehyd in verd. wss. H2SO4 fuehrt zu 1-Phenyl-1,2,3,4tetrahydro-β-carbolin (S.179)

Freter,K. et al.; Justus Liebigs Annalen der Chemie; vol. 684; (1965); p. 159 - 187, View in Reaxys

Hydrobromid: Rk. m. N-Brom-succinimid in wss. tertButylalkohol (MolVerh. 1:1) fuehrt zu 3-(2-Aminoethyl)-oxindol*HBr

Hinman; Bauman; Journal of Organic Chemistry; vol. 29; (1964); p. 1206, View in Reaxys

Nω-Benzamid: Rk. m. N-Bromsuccinimid in wss. tert-Butylalkohol (Mol-Verh. 1:1) fuehrt zu 3-(2Benzamino-ethyl)-oxindol

Hinman; Bauman; Journal of Organic Chemistry; vol. 29; (1964); p. 1206, View in Reaxys

Hydrochlorid: Rk. m. 3,4-Dimethoxy-phenyl-acetaldehyd/A.+W. in A.+2N H2SO4 (Raumtemp., 24 h) fuehrt zu 1(3,4-Dimethoxybenzyl)-1,2,3,4tetrahydro-β-carbolin-HCl

Taborsky; McIsaac; Journal of Medicinal Chemistry; vol. 7; (1964); p. 135,140, View in Reaxys

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2016-06-21 14:42:30

Acetat: F: 134.5-135.5grad

Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys

Hydrochlorid: Rk. m. (3,4-Dihydroxyphenyl)-brenztraubensaeure, W. (2 Wochen, 20grad) -> 1-(3,4Dihydroxybenzyl)-1,2,3,4-tetrahydro-β-carbolin-1-carbonsaeure; bei 12 h kochen (N2) -> 1(3,4-Dihydroxybenzyl)-1,2,3,4tetrahydro-β-carbolin (I R=H)

Harley-Mason; Waterfield; Tetrahedron; vol. 19; (1963); p. 65,71, View in Reaxys

Pikrat C10H12N2*C6H3 N3O7: F: 246grad (korr.); F: 247-248grad (A., korr.); rot

Piozzi; Merlini; Gazzetta Chimica Italiana; vol. 92; (1962); p. 1105,1107-1116, View in Reaxys

Hydrochlorid: F: 116grad

Bocourt; Vignau; Bulletin de la Societe Chimique de France; (1961); p. 1190, View in Reaxys

Chlorhydrat: F: 246-247grad

Matkovics et al.; Acta Physica et Chemica; vol. 7; (1961); p. 51, View in Reaxys

Hydrochlorid C10H12N2*HCl: IR-Sp. (6-11 μ) d. wss. Lsg.

Kirschenbaum; Parker; Spectrochimica Acta; vol. 17; (1961); p. 785,789; Chem.Abstr.; nb. 16254; (1960), View in Reaxys

2,4-DinitrophenylDerivat: F: 217grad

Asatoor; Journal of Chromatography; vol. 4; (1960); p. 144,145-152; Chem.Abstr.; vol. 56; nb. 9393; (1962), View in Reaxys

Hydrochlorid C10H12N2*HCl: F: 248-252grad (A., Kofler)

Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys

o-tolyl acetate (mp: 170 degree ); Further Data see Handbook

Julian et al.; Journal of the American Chemical Society; vol. 70; (1948); p. 180,182, View in Reaxys

Melting Point (30) 1 of 30

Melting Point [°C]

110 - 112

Guo, Xiaoke; Yang, Qian; Xu, Jing; Zhang, Li; Chu, Hongxi; Yu, Peng; Zhu, Yingying; Wei, Jinglian; Chen, Weilin; Zhang, Yaozhong; Zhang, Xiaojin; Sun, Haopeng; Tang, Yiqun; You, Qidong; Bioorganic and Medicinal Chemistry; vol. 21; nb. 21; (2013); p. 6466 - 6476, View in Reaxys 2 of 30

Melting Point [°C]

111 - 112

Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys; Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys 3 of 30

Melting Point [°C]

111 - 112

Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys 4 of 30

Melting Point [°C]

112 - 113

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys

18/155

2016-06-21 14:42:30

5 of 30

Melting Point [°C]

119

Mortoni, Annalisa; Martinelli, Marisa; Piarulli, Umberto; Regalia, Nickolas; Gagliardi, Stefania; Tetrahedron Letters; vol. 45; nb. 35; (2004); p. 6623 - 6627, View in Reaxys 6 of 30

Melting Point [°C]

116 - 117

Solvent (Melting Point)

acetone

Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys 7 of 30

Melting Point [°C]

114 - 119

Wang, Alan P. L.; Li, Liang; Analytical Chemistry; vol. 64; nb. 7; (1992); p. 769 - 775, View in Reaxys 8 of 30

Melting Point [°C]

114 - 115

Barton et al.; Journal of the Chemical Society; (1965); p. 3990,3993, View in Reaxys; Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 21; nb. 4; (1985); p. 502 - 509; Khimiya Prirodnykh Soedinenii; vol. 21; nb. 4; (1985); p. 536 - 544, View in Reaxys 9 of 30

Melting Point [°C]

116 - 117

Solvent (Melting Point)

benzene

Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys; Deetz, J. S.; Behrman, E. J.; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 135 - 140, View in Reaxys 10 of 30

Melting Point [°C]

115

Fleming,I.; Woolias,M.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 829 - 837, View in Reaxys 11 of 30

Melting Point [°C]

116 - 117.5

Takano et al.; Heterocycles; vol. 6; (1977); p. 1167,1168, 1169, 1170, View in Reaxys 12 of 30

Melting Point [°C]

118 - 120

Buzas et al.; Synthesis; (1977); p. 129, View in Reaxys; Patent; Richter Gedeon Vegyeszeti Gyar R.T.; FR2261271; (1973); DE2344919; Chem.Abstr.; vol. 80; nb. 146016, View in Reaxys; Szantay et al.; Synthesis; (1974); p. 354, View in Reaxys 13 of 30

Melting Point [°C]

110 - 112

Patent; Grandberg; Bobrowa; SU451696; (1976); Ref. Zh., Khim.; vol. 8; nb. O143P; (1976), View in Reaxys 14 of 30

Melting Point [°C]

112

Konda; Suzuki; Omura; Onda; Chemical and Pharmaceutical Bulletin; vol. 24; nb. 1; (1976); p. 92 - 96, View in Reaxys 15 of 30

Melting Point [°C]

240 - 242

Suvorov et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 1600,1565,1568, View in Reaxys 16 of 30

Melting Point [°C]

114 - 116

Suvorov et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1316,1320; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1496, View in Reaxys 17 of 30

Melting Point [°C]

113 - 114

Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys 18 of 30

Melting Point [°C]

117 - 118

Bergman,J. et al.; Tetrahedron; vol. 29; (1973); p. 971 - 976, View in Reaxys 19 of 30

Melting Point [°C]

112 - 113

Solvent (Melting Point)

petroleum ether; benzene

Grandberg et al.; Sintezy Geterotsiklicheskikh Soedinenii; vol. 9; (1972); p. 18; Chem.Abstr.; vol. 79; nb. 146321, View in Reaxys 20 of 30

Melting Point [°C]

115 - 117

19/155

2016-06-21 14:42:30

Johns et al.; Australian Journal of Chemistry; vol. 19; (1966); p. 893, View in Reaxys 21 of 30

Melting Point [°C]

118

Solvent (Melting Point)

petroleum ether

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys 22 of 30

Melting Point [°C]

114

Solvent (Melting Point)

diethyl ether

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys 23 of 30

Melting Point [°C]

118

Manske; Canadian Journal of Research; vol. 5; (1931); p. 599; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 2475, View in Reaxys; Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys 24 of 30

Melting Point [°C]

114

Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys; Julia et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 251; (1960); p. 394, View in Reaxys 25 of 30

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys

26 of 30

Melting Point [°C]

102 - 103

Solvent (Melting Point)

hexane

Piozzi; Merlini; Gazzetta Chimica Italiana; vol. 92; (1962); p. 1105,1107-1116, View in Reaxys 27 of 30

Melting Point [°C]

116

Matkovics et al.; Acta Physica et Chemica; vol. 7; (1961); p. 51, View in Reaxys; Patent; Lab.francais de chimiotherapie; US2920080; (1960); Chem.Abstr.; vol. 54; nb. 13018hi; (1960), View in Reaxys 28 of 30

Melting Point [°C]

242 - 244

Mndzhoyan; Papayan; Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki; vol. 14; (1961); p. 603; Chem.Abstr.; vol. 58; nb. 4497c; (1963), View in Reaxys 29 of 30

Melting Point [°C]

116 - 118

Ahmad et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 2523, View in Reaxys 30 of 30

Melting Point [°C]

120

Asahina; Acta Phytochimica; vol. 1; (1922); p. 81; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 248, View in Reaxys Boiling Point (6) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

Location

References

137

0.15

supporting information

Pablos, Jess L.; Vallejos, Sal; Muoz, Asuncin; Rojo, Mara J.; Serna, Felipe; Garca, Flix C.; Garca, Jos M.; Chemistry - A European Journal; vol. 21; nb. 24; (2015); p. 8733 - 8736, View in Reaxys

140 - 155

0.3

Takano et al.; Heterocycles; vol. 6; (1977); p. 1167,1168, 1169, 1170, View in Reaxys

185 - 187

0.5

Patent; Grandberg; Bobrowa; SU451696; (1976); Ref. Zh., Khim.; vol. 8; nb. O143P; (1976), View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 943; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1085, View in Reaxys

185 - 188

0.5

Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys

143 - 146

0.8

Pfeil,E.; Harder,U.; Angewandte Chemie; vol. 79; (1967); p. 188, View in Reaxys

121

0.01 - 0.02

de Groot,S.; Strating,J.; Recueil des Travaux Chimiques des PaysBas; vol. 80; (1961); p. 121 - 133, View in Reaxys

Association (MCS) (33)

20/155

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1 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

acetonitrile

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

2',4',6'-trimethyl-3',5'-bis(4-phenyl-4,5-dihydrooxazol-2-ylmethyl)biphenyl-2-ol

Chung, Yun Mi; Raman, Balamurali; Ahn, Kyo Han; Tetrahedron; vol. 62; nb. 50; (2006); p. 11645 - 11651, View in Reaxys 2 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

aq. phosphate buffer

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

cucurbit[8]uril; paraquat dichloride

Bush, Meghan E.; Bouley, Nicole D.; Urbach, Adam R.; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14511 - 14517, View in Reaxys 3 of 33

Description (Association Enthalpy of association (MCS)) Solvent (Association (MCS))

aq. phosphate buffer

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

cucurbit[8]uril; paraquat dichloride

Bush, Meghan E.; Bouley, Nicole D.; Urbach, Adam R.; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14511 - 14517, View in Reaxys 4 of 33

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

D2O

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

cucurbit[8]uril; paraquat dichloride

Bush, Meghan E.; Bouley, Nicole D.; Urbach, Adam R.; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14511 - 14517, View in Reaxys 5 of 33

Description (Association IR spectrum of the complex (MCS)) Partner (Association (MCS))

H2O

Carney; Dian; Florio; Zwier; Journal of the American Chemical Society; vol. 123; nb. 23; (2001); p. 5596 - 5597, View in Reaxys 6 of 33

Description (Association Further physical properties of the complex (MCS)) Solvent (Association (MCS))

D2O; various solvent(s)

Temperature (Association (MCS)) [°C]

29.9

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Partner (Association (MCS))

calf thymus DNA sodium salt

Sartorius, Joachim; Schneider, Hans-Joerg; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1997); p. 2319 - 2327, View in Reaxys 7 of 33

Description (Association Dipole moment of the complex (MCS)) Solvent (Association (MCS))

1,2-dichloro-ethane

Partner (Association (MCS))

Abu-Eittah; Abdou; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 93; nb. 11-12; (1996); p. 1958 - 1973, View in Reaxys 8 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

bovine serum albumin (BSA)

Okabe; Adachi; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 2; (1992); p. 499 - 500, View in Reaxys 9 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

D2O

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

C50H60N8O12

Kikuchi, Jun-ichi; Egami, Kazuko; Suehiro, Kazuaki; Murakami, Yukito; Chemistry Letters; nb. 9; (1992); p. 1685 - 1688, View in Reaxys 10 of 33

Description (Association Further physical properties of the complex (MCS)) Solvent (Association (MCS))

D2O

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

C50H60N8O12

Kikuchi, Jun-ichi; Egami, Kazuko; Suehiro, Kazuaki; Murakami, Yukito; Chemistry Letters; nb. 9; (1992); p. 1685 - 1688, View in Reaxys 11 of 33

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

CDCl3

Partner (Association (MCS))

Rebek's cleft

Rebek, J.; Askew, B.; Ballester, P.; Costero, A.; Journal of the American Chemical Society; vol. 110; nb. 3; (1988); p. 923 - 927, View in Reaxys 12 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

2-Methylcyclohexanol

22/155

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Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 13 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

benzene

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 14 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

acetone

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 15 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

dichloromethane

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 16 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

H2O

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 17 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

methanol

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 18 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

ethanol

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 19 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

propan-1-ol

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 20 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

isopropyl alcohol

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 21 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

2-methyl-propan-1-ol

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 22 of 33

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

tert-Amyl alcohol

23/155

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Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 23 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

thymidine 5'-phosphate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 24 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

thymidine 5'-phosphate; sodium cacodylate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 25 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

disodium uridine-5'-monophosphate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 26 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

disodium uridine-5'-monophosphate; sodium cacodylate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 27 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

adenosine 5'-monophosphate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 28 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

adenosine 5'-monophosphate; sodium cacodylate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 29 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

24/155

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Partner (Association (MCS))

guanosine-5'-monophosphoric acid disodium salt

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 30 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

guanosine-5'-monophosphoric acid disodium salt; sodium cacodylate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 31 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

cytidine monophosphate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 32 of 33

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

H2O

Partner (Association (MCS))

cytidine monophosphate; sodium cacodylate

Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 33 of 33

Description (Association Association with compound (MCS)) Helene et al.; Biochemistry; vol. 10; (1971); p. 3802,3806, View in Reaxys; McMenamy; Journal of Biological Chemistry; vol. 240; (1965); p. 4235,4236 - 4238, View in Reaxys

Chromatographic Data (4) Chromatographic Location data HPLC (High performance liquid chromatography) HPLC (High performance liquid chromatography)

References Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518, View in Reaxys; Kalb, Daniel; Gressler, Julia; Hoffmeister, Dirk; ChemBioChem; vol. 17; nb. 2; (2016); p. 132 - 136, View in Reaxys

supporting information

Ren, Adeline; Martinez, Jean; Cavelier, Florine; European Journal of Organic Chemistry; vol. 2014; nb. 36; (2014); p. 8142 - 8147, View in Reaxys

LC (Liquid chromatography)

Bracchitta, Giuseppina; Catalfo, Alfio; De Guidi, Guido; Photochemical and Photobiological Sciences; vol. 12; nb. 6; (2013); p. 967 - 973, View in Reaxys

UPLC (Ultra performance liquid chromatography)

Rangiah, Kannan; Palakodeti, Dasaradhi; Rapid Communications in Mass Spectrometry; vol. 27; nb. 21; (2013); p. 2439 - 2452, View in Reaxys

Conformation (3) Object of Investi- References gation Conformation

Culvenor,C.C.J.; Ham,N.S.; Australian Journal of Chemistry; vol. 27; (1974); p. 2191 - 2198, View in Reaxys; Kumbar; Sankar; Journal of the American Chemical Society; vol. 97; (1975); p. 7411,7412-7416, View in Reaxys; Philips, Laura A.; Levy, Donald H.; Journal of Physical Chemistry; vol. 90; nb. 21; (1986); p. 4921 - 4923, View in Reaxys; Feng, Ke; Kleinermanns, Karl; Chemical Physics Letters; vol. 473; nb. 4-6; (2009); p. 220 - 222, View in Reaxys

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The author investigated the; Conformation

Carney, Joel R.; Zwier, Timothy S.; Chemical Physics Letters; vol. 341; nb. 1-2; (2001); p. 77 - 85, View in Reaxys; Schmitt, Michael; Boehm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo; Journal of the American Chemical Society; vol. 127; nb. 29; (2005); p. 10356 - 10364, View in Reaxys; Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys

Conformer equilibrium

Philips, Laura A.; Levy, Donald H.; Journal of Chemical Physics; vol. 89; nb. 1; (1988); p. 85 - 90, View in Reaxys

Crystal Phase (1) Description (Crys- References tal Phase) Crystal structure determination

Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys

Crystal Property Description (6) Colour & Other Location Properties red

Paragraph 0045

References Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys

white

Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; AlaouiJamali, Moulay A.; Jiang, Tao; Marine Drugs; vol. 11; nb. 5; (2013); p. 1427 - 1439, View in Reaxys

brown

Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys

yellow

red

supporting information

Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8564 - 8567, View in Reaxys

white

supporting information

Nicolaou; Krasovskiy, Arkady; Trepanier, Vincent E.; Chen, David Y.-K.; Angewandte Chemie - International Edition; vol. 47; nb. 22; (2008); p. 4217 - 4220, View in Reaxys; Nicolaou, K. C.; Krasovskiy, Arkady; Majumder, Utpal; Trepanier, Vincent E.; Chen, David Y.-K.; Journal of the American Chemical Society; vol. 131; (2009); p. 3690 - 3699, View in Reaxys

Crystal System (1) Crystal System References rhombic

Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys

Dielectric Constant (1) References Kumbar; Sankar; Journal of the American Chemical Society; vol. 97; (1975); p. 7411,7412-7416, View in Reaxys Dissociation Exponent (14) 1 of 14

Dissociation Exponent (pK)

10.2

Solvent (Dissociation Exponent)

water

Type (Dissociation Exponent)

b1/apparent

Comment (Dissociation Exponent)

Samoylenko, Volodymyr; Ashfaq, Mohammad K.; Jacob, Melissa R.; Tekwani, Babu L.; Khan, Shabana I.; Manly, Susan P.; Joshi, Vaishali C.; Walker, Larry A.; Muhammad, Ilias; Journal of Natural Products; vol. 72; nb. 1; (2009); p. 92 - 98, View in Reaxys 2 of 14

Dissociation Exponent (pK)

4.2

Dissociation Group

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Method (Dissociation Exponent)

spectrophotometric

Type (Dissociation Exponent)

a1/apparent

Hela; Anipindi; Priyadarsini; O'Neill; Journal of Physical Chemistry B; vol. 103; nb. 40; (1999); p. 8606 - 8611, View in Reaxys 3 of 14

Dissociation Exponent (pK)

10.18

Temperature (Dissociation Exponent) [°C]

Type (Dissociation Exponent)

a1/apparent

Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys 4 of 14

Dissociation Exponent (pK)

10.35

Temperature (Dissociation Exponent) [°C]

Type (Dissociation Exponent)

a1/apparent

Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys 5 of 14

Comment (Dissociation Exponent)

(pk')pK(a) (S.7140) nach D.D.Perrin 'Dissociation Constants of Organic Bases in Aqueous Solution', Butterworths, London, 1965, p.239

Svejda et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 7138, View in Reaxys 6 of 14

Comment (Dissociation Exponent)

(pk')pK(2)

Nowotarska; Podkowinska; Roczniki Chemii; vol. 50; (1976); p. 789,790, 791, 793, View in Reaxys 7 of 14

Comment (Dissociation Exponent)

(pk')pK (Tab. I)

Chen; Hoffmann; Journal of Physical Chemistry; vol. 78; (1974); p. 2099, View in Reaxys 8 of 14

Comment (Dissociation Exponent)

(pk')pK(b)

Julia; Lallemand; Bulletin de la Societe Chimique de France; (1973); p. 2058,2059, 2061, View in Reaxys 9 of 14

Comment (Dissociation Exponent)

(pk')pK(a)

Marziano et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 1915,1917, View in Reaxys 10 of 14

Comment (Dissociation Exponent)

(pk')pK (S.2099)

Weber; Simeon; Journal of Inorganic and Nuclear Chemistry; vol. 33; (1971); p. 2097,2099, View in Reaxys 11 of 14

Comment (Dissociation Exponent)

(pk')Mess. d. pK-Werte (S.2858)

Yagil; Tetrahedron; vol. 23; nb. 6; (1967); p. 2855 - 2861, View in Reaxys 12 of 14

Comment (Dissociation Exponent)

(pk')pK(a) (50percent-ig. wss. A.): 8.69

Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys 13 of 14

Comment (Dissociation Exponent)

(pk')pK(a) (H+) (25grad, photom.): -6.31 (Thermodyn. .... wegen grosser Verd.)

Hinman; Lang; Journal of the American Chemical Society; vol. 86; (1964); p. 3796,3797,3804, View in Reaxys

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14 of 14

Dissociation Exponent (pK)

10.2

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a/apparent

Vane; British Journal of Pharmacology and Chemotherapy; vol. 14; (1959); p. 87,91, View in Reaxys Electrical Moment (3) 1 of 3

Description (Electrical Moment)

Dipole moment

Moment (Electrical Moment) [D]

1.6 - 2.7

Method (Electrical Moment)

Stark effect

Solvent (Electrical Moment)

vapour

Comment (Electrical Moment)

various conformers. Object(s) of Study: ground state

Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys 2 of 3

Description (Electrical Moment)

Dipole moment

Moment (Electrical Moment) [D]

1.4 - 2.5

Method (Electrical Moment)

Stark effect

Solvent (Electrical Moment)

vapour

Comment (Electrical Moment)

various conformers. Object(s) of Study: excited singlet state

Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys 3 of 3

Description (Electrical Moment)

Dipole moment

Kumbar; Sankar; Journal of the American Chemical Society; vol. 97; (1975); p. 7411,7412-7416, View in Reaxys Electrochemical Behaviour (2) Description (Elec- References trochemical Behaviour) Protonation

Box, Karl; Bevan, Christopher; Comer, John; Hill, Alan; Allen, Ruth; Reynolds, Derek; Analytical Chemistry; vol. 75; nb. 4; (2003); p. 883 - 892, View in Reaxys

Electrolytic dissociation / protonation equilibrium

Balon, Manuel; Hidalgo, Jose; Guardado, Pilar; Munoz, Maria A.; Carmona, Carmen; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1993); p. 91 - 97, View in Reaxys

Electrochemical Characteristics (2) 1 of 2

Description (Electrochemical Characteristics)

Electrochemical characteristics given

Estevao, Monica S.; Carvalho, Luisa C.; Ferreira, Luisa M.; Fernandes, Eduarda; Marques, M. Manuel B.; Tetrahedron Letters; vol. 52; nb. 1; (2011); p. 101 - 106, View in Reaxys

28/155

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2 of 2

Description (Electrochemical Characteristics)

polarographic half-wave potential

Solvent (Electrochemical Characteristics)

aq. phosphate buffer; dimethylformamide

Levina; Chechekin; Arzamastsev; Gaevskii; Degterev; Grigor'ev; Pharmaceutical Chemistry Journal; vol. 32; nb. 10; (1998); p. 557 - 558, View in Reaxys Further Information (32) Description (Fur- References ther Information) Further information

Wood et al.; Analytical Chemistry; vol. 48; (1976); p. 981, View in Reaxys

Further information

Wakahara et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 2481,2482-2486, View in Reaxys

Further information

Andrews; Forster; Biochemistry; vol. 11; nb. 10; (1972); p. 1875 - 1879, View in Reaxys

Further information

Persson; Acta Pharmaceutica Suecica; vol. 8; (1971); p. 193,198, View in Reaxys

Further information

Obtemperanskaya; Likhosherstova; J. Anal. Chem. USSR (Engl. Transl.); vol. 26; (1971); p. 158,140, View in Reaxys

Further information

Vinnik et al.; Russian Journal of Physical Chemistry; vol. 44; (1970); p. 1621,1624, View in Reaxys

Further information

Bowd et al.; Photochemistry and Photobiology; vol. 11; (1970); p. 445,447, View in Reaxys

Further information

Jamieson; Hutzinger; Phytochemistry (Elsevier); vol. 9; (1970); p. 2029,2033, View in Reaxys

Further information

Wakahara; Fujiwara; Tomita; Tetrahedron letters; vol. 57; (1970); p. 4999 - 5002, View in Reaxys

Further information

Obtemperanskaya et al.; J. Anal. Chem. USSR (Engl. Transl.); vol. 25; (1970); p. 2033,1744, View in Reaxys

Further information

Borg et al.; Journal of Pharmacy and Pharmacology; vol. 22; (1970); p. 507,508,509, View in Reaxys

Further information

Kitaoka; Nakano; Journal of Biochemistry (Tokyo, Japan); vol. 66; (1969); p. 87,91, View in Reaxys

Further information

Keglevic et al.; Croatica Chemica Acta; vol. 40; (1968); p. 7,10, View in Reaxys

Further information

Millie et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 207,209,210, View in Reaxys

Further information

Smaller et al.; Journal of Chemical Physics; vol. 46; (1967); p. 3976,3979, View in Reaxys

Further information

Eichele; Mutschler; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 300; nb. 12; (1967); p. 1038, View in Reaxys

Further information

Sugiyama et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 348,349, View in Reaxys

Further information

Wilson; Biochemistry; vol. 5; (1966); p. 1351,1355, View in Reaxys

Further information

Brubacher,L.J.; Bender,M.L.; Journal of the American Chemical Society; vol. 88; (1966); p. 5871 - 5880, View in Reaxys

Further information

Fleming et al.; Analytical Chemistry; vol. 37; (1965); p. 692,693, View in Reaxys

Further information

Krupka; Biochemistry; vol. 4; (1965); p. 429,431, View in Reaxys

Further information

Freter,K. et al.; Justus Liebigs Annalen der Chemie; vol. 684; (1965); p. 159 - 187, View in Reaxys

29/155

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Further information

Hinman; Bauman; Journal of Organic Chemistry; vol. 29; (1964); p. 1206, View in Reaxys

Further information

Taborsky; McIsaac; Journal of Medicinal Chemistry; vol. 7; (1964); p. 135,140, View in Reaxys

Further information

Harley-Mason; Waterfield; Tetrahedron; vol. 19; (1963); p. 65,71, View in Reaxys

Further information

Trojanek et al.; Tetrahedron Letters; (1961); p. 702,706, View in Reaxys

Further information

Kirschenbaum; Parker; Spectrochimica Acta; vol. 17; (1961); p. 785,789; Chem.Abstr.; nb. 16254; (1960), View in Reaxys

Further information

Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys

Further information

Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 8; (1960); p. 294,296, View in Reaxys

Further information

Knowlton et al.; Analytical Chemistry; vol. 32; (1960); p. 666, View in Reaxys

Further information

Harley-Mason; Waterfield; Chemistry and Industry (London, United Kingdom); (1960); p. 1478, View in Reaxys

Further information

Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys

Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles

Method of determination: powder X-ray diffraction

Liquid Phase (1) Description (Liquid Phase)

References

Self-association in solution

Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys

Helene; Dimicoli; Journal of the American Chemical Society; vol. 95; (1973); p. 1036, View in Reaxys

Liquid/Liquid Systems (MCS) (4) 1 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

Partner (Liquid/Liquid Systems (MCS))

toluene

Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 2 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

Partner (Liquid/Liquid Systems (MCS))

cyclohexane

Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 3 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

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Partner (Liquid/Liquid Systems (MCS))

chloroform

Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 4 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Kang; Green; Nature (London, United Kingdom); vol. 222; (1969); p. 794, View in Reaxys Molecular Deformation (2) Description (MoComment (Molec- References lecular Deforma- ular Deformation) tion) Rotational constants Rotational constants

Schmitt, Michael; Boehm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo; Journal of the American Chemical Society; vol. 127; nb. 29; (2005); p. 10356 - 10364, View in Reaxys two conformers

Caminati, Walther; Physical Chemistry Chemical Physics; vol. 6; nb. 10; (2004); p. 2806 - 2809, View in Reaxys

Partition octan-1-ol/water (MCS) (2) 1 of 2

log POW

2.147

Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 2 of 2

log POW

1.35

Temperature (Partition octan-1-ol/water (MCS)) [°C]

24.85

Guardado, Pilar; Balon, Manuel; Carmona, Carmen; Munoz, Maria A.; Domene, Carmen; Journal of Pharmaceutical Sciences; vol. 86; nb. 1; (1997); p. 106 - 109, View in Reaxys Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

insoluble in buffer

Singudas, Rohith; Adusumalli, Srinivasa Rao; Joshi, Pralhad Namdev; Rai, Vishal; Chemical Communications; vol. 51; nb. 3; (2015); p. 473 - 476, View in Reaxys Space Group (1) Space Group 19

References Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys

Transport Phenomena (MCS) (1) 1 of 1

Description (Transport Phenomena (MCS))

Diffusion

Temperature (Transport 25 Phenomena (MCS)) [°C] Partner (Transport Phenomena (MCS))

aq. sodium phosphate buffer

Robinson, David; Anderson, James E.; Lin, Jeong-long; Journal of Physical Chemistry; vol. 94; nb. 2; (1990); p. 1003 - 1005, View in Reaxys NMR Spectroscopy (32) 1 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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Original Text (NMR Spectroscopy)

Location

Paragraph 0045

NMR (400 MHz, DMSO-d6) δ 10.8 (br, 1H), 7.65 (brd, J = 7.6 Hz, 1H), 7.32 (brd, J = 8.0 Hz, 1H), 6.62-6.50 (d, J = 2.4 Hz, 1H), 7.05 (dd, J = 1.2, 8.0 Hz, 1H), 6.95 (dd, J = 1.2, 7.6 Hz, 1H), 2.82-2.71 (m, 4H), 2.52 (br, 2H)

Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys 2 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C NMR (100 MHz, CDCl ) δ 136.31, 127.38, 122.63, 120.86, 118.38, 118.26, 112.60, 3 111.37, 42.73, 29.48

Location

Paragraph 0045

Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys 3 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

250.1

Carvalho, Marcos A.; Arruda, Eduardo G.R.; Profirio, Daniel M.; Gomes, Alexandre F.; Gozzo, Fbio C.; Formiga, Andr L.B.; Corbi, Pedro P.; Journal of Molecular Structure; vol. 1100; (2015); p. 6 - 13; Art.No: 21675, View in Reaxys 4 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

62.9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

15N

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

32/155

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys 7 of 32

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys 8 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Huan, Uozhen; Klin, Beata; Darras, Fouad H.; Heilmann, Joer; Decker, Michael; European Journal of Medicinal Chemistry; vol. 81; (2014); p. 15 - 21, View in Reaxys 9 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; Alaoui-Jamali, Moulay A.; Jiang, Tao; Marine Drugs; vol. 11; nb. 5; (2013); p. 1427 - 1439, View in Reaxys 10 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

151

Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; Alaoui-Jamali, Moulay A.; Jiang, Tao; Marine Drugs; vol. 11; nb. 5; (2013); p. 1427 - 1439, View in Reaxys 11 of 32

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

33/155

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Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys 12 of 32

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys 13 of 32

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Zhu, Yan-Ping; Liu, Mei-Cai; Cai, Qun; Jia, Feng-Cheng; Wu, An-Xin; Chemistry - A European Journal; vol. 19; nb. 31; (2013); p. 10132 - 10137, View in Reaxys 14 of 32

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8564 - 8567, View in Reaxys 15 of 32

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

34/155

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Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8564 - 8567, View in Reaxys 16 of 32

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Ankner, Tobias; Hilmersson, Goeran; Organic Letters; vol. 11; nb. 3; (2009); p. 503 - 506, View in Reaxys 17 of 32

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3), δ 8.35 (broad s, 1H), 7.64 (d, J=7.91 Hz, 1H), 7.44-7.32 (m, 1H), 7.26-7.18 (m, 1H), 7.18-7.09 (m, 1H), 7.04 (d, J=2.26 Hz, 1H), 1.36 (broad s, 2H), 3.11-3.01 (m, 2H), 2.99-2.86 (m, 2H)

Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys 18 of 32

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

13C NMR (CDCl ) δ 136.44, 127.49, 122.06, 121.96, 119.21, 118.87, 113.69, 111.16, 3 42.34, 29.49

Comment (NMR Spectroscopy)

Signals given

Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys 19 of 32

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300.13

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3), 8.35 (broad s, 1H), 7.64 (d, J=7.91 Hz, 1H), 7.44 - 7.32 (m, 1H), 7.26 7.18 (m, 1H), 7.18 - 7.09 (m, 1H), 7.04 (d, J=2.26 Hz, 1H), 1.36 (broad s, 2H), 3.11 - 3.01 (m,2H), 2.99 - 2.86 (m, 2H)

Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys 20 of 32

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

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Frequency (NMR Spectroscopy) [MHz]

75.43

Original Text (NMR Spectroscopy)

13C NMR (CDCl ) 136.44, 127.49, 122.06, 121.96, 119.21, 118.87, 113.69, 111.16, 42.34, 3 29.49

Comment (NMR Spectroscopy)

Signals given

Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys 21 of 32

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600.468

Maresh, Justin J.; Giddings, Lesley-Ann; Friedrich, Anne; Loris, Elke A.; Panjikar, Santosh; Trout, Bernhardt L.; Stoeckigt, Joachim; Peters, Baron; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 130; nb. 2; (2008); p. 710 - 723, View in Reaxys 22 of 32

Description (NMR Spec- 2D-NMR troscopy) Nucleus (NMR Spectroscopy)

13C; 1H

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300.13

Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys 24 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

75.43

Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys 25 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

36/155

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Frequency (NMR Spectroscopy) [MHz]

300

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 26 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Diallo. A. O.; Mehri, H.; Iouzalen, L.; Plat, M.; Phytochemistry (Elsevier); vol. 40; nb. 3; (1995); p. 975 - 978, View in Reaxys; Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys 27 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys 28 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Sato, Hiroji; Kawagishi, Hirokazu; Nishimura, Tsutomu; Yoneyama, Syozou; Yoshimoto, Yuko; et al.; Agricultural and Biological Chemistry; vol. 49; nb. 10; (1985); p. 2969 - 2974, View in Reaxys 29 of 32

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Ernst, Ludger; Kang, Sungzong; Journal of Chemical Research, Miniprint; nb. 9; (1981); p. 3019 - 3038, View in Reaxys 30 of 32

Description (NMR Spec- NMR troscopy) Konda; Suzuki; Omura; Onda; Chemical and Pharmaceutical Bulletin; vol. 24; nb. 1; (1976); p. 92 - 96, View in Reaxys; Helene; Dimicoli; Journal of the American Chemical Society; vol. 95; (1973); p. 1036, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys

31 of 32

Description (NMR Spec- Spin-spin coupling constants troscopy) Culvenor,C.C.J.; Ham,N.S.; Australian Journal of Chemistry; vol. 27; (1974); p. 2191 - 2198, View in Reaxys

32 of 32

Description (NMR Spec- Spectrum troscopy) Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys

IR Spectroscopy (3)

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1 of 3

Description (IR Spectroscopy)

Bands

Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 8; (1960); p. 294,296, View in Reaxys; Carvalho, Marcos A.; Arruda, Eduardo G.R.; Profirio, Daniel M.; Gomes, Alexandre F.; Gozzo, Fbio C.; Formiga, Andr L.B.; Corbi, Pedro P.; Journal of Molecular Structure; vol. 1100; (2015); p. 6 - 13; Art.No: 21675, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys; De Antoni et al.; Gazzetta Chimica Italiana; vol. 100; (1970); p. 1039,1042, 1044, View in Reaxys Mass Spectrometry (18) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

References

liquid chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Kalb, Daniel; Gressler, Julia; Hoffmeister, Dirk; ChemBioChem; vol. 17; nb. 2; (2016); p. 132 - 136, View in Reaxys

liquid chromatog- Page/Page colraphy mass spec- umn 85 trometry (LCMS); spectrum

Patent; UCL BUSINESS PLC; MARSON, Charles Michael; FERRETTI, Patrizia; WO2014/188193; (2014); (A1) English, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys

tandem mass spectrometry; CID (collision-induced dissociation); electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum

Rangiah, Kannan; Palakodeti, Dasaradhi; Rapid Communications in Mass Spectrometry; vol. 27; nb. 21; (2013); p. 2439 - 2452, View in Reaxys

liquid chromatography mass spectrometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; spectrum

Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Casale, Rosario; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 61; nb. 21; (2013); p. 5156 5162, View in Reaxys

spectrum

Elam, Jeffrey W.; Levy, Donald H.; Journal of Physical Chemistry B; vol. 102; nb. 41; (1998); p. 8113 - 8120, View in Reaxys; Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518,7, View in Reaxys; Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela,

38/155

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Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518, View in Reaxys LCMS (Liquid chromatography mass spectrometry); Spectrum

Urayama, Shiro; Zou, Wei; Brooks, Kindra; Tolstikov, Vladimir; Rapid Communications in Mass Spectrometry; vol. 24; nb. 5; (2010); p. 613 - 620, View in Reaxys

ESI (Electrospray ionisation)

Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys

ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry)

Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys

ESI (Electrospray ionisation)

Molecular peak

Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys

ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry)

Molecular peak

Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys

spectrum; tandem mass spectrometry

Williamson, Brian L.; Benson, Linda M.; Tomlinson, Andy J.; Mayeno, Arthur N.; Gleich, Gerald J.; Naylor, Stephen; Toxicology Letters; vol. 92; nb. 2; (1997); p. 139 - 148, View in Reaxys

fragmentation pattern

MIKE (mass ion kinetic energy)

Bertazzo, Antonella; Catinella, Silvia; Traldi, Pietro; Journal of Mass Spectrometry; vol. 31; nb. 7; (1996); p. 735 - 740, View in Reaxys

spectrum; electron impact (EI)

FAB (fast atom bombardment)

Bertazzo, Antonella; Catinella, Silvia; Traldi, Pietro; Journal of Mass Spectrometry; vol. 31; nb. 7; (1996); p. 735 - 740, View in Reaxys

spectrum

laser desorption

Hrubowchak; Ervin; Wood; Winograd, Nicholas; Analytical Chemistry; vol. 63; nb. 18; (1991); p. 1947 - 1953, View in Reaxys; Tembreull; Lubman; Analytical chemistry; vol. 59; nb. 8; (1987); p. 1082 - 1088, View in Reaxys; Li, Liang; Lubman, David M.; Analytical Chemistry; vol. 61; nb. 17; (1989); p. 1911 - 1915, View in Reaxys; Wang, Alan P. L.; Guo, Xijian; Li, Liang; Analytical Chemistry; vol. 66; nb. 21; (1994); p. 3664 - 3675, View in Reaxys

spectrum; electron impact (EI)

Gynther, Jukka; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 42; nb. 7; (1988); p. 433 - 441, View in Reaxys

spectrum; chemical ionization (CI)

Gynther, Jukka; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 42; nb. 7; (1988); p. 433 - 441, View in Reaxys Reisch et al.; Journal of Pharmacy and Pharmacology; vol. 20; (1968); p. 81,85, View in Reaxys; Jamieson; Hutzinger; Phytochemistry (Elsevier); vol. 9; (1970); p. 2029,2033, View in Reaxys; Milne et al.; Analytical Chemistry; vol. 45; (1973); p. 1952,1953, View in Reaxys; Chmel'nickij et al.; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 417,406, View in Reaxys; Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, View in Reaxys; Ghosal; Srivastava; Phytochemistry (Elsevier); vol. 12; (1973); p. 193,196, View in Reaxys

UV/VIS Spectroscopy (18) 1 of 18

Description (UV/VIS Spectroscopy)

Spectrum

LeGreve, Tracy A.; Baquero, Esteban E.; Zwier, Timothy S.; Journal of the American Chemical Society; vol. 129; nb. 13; (2007); p. 4028 - 4038, View in Reaxys; Kalb, Daniel; Gressler, Julia; Hoffmeister, Dirk; ChemBioChem; vol. 17; nb. 2; (2016); p. 132 - 136, View in Reaxys 2 of 18

Description (UV/VIS Spectroscopy)

Spectrum

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Solvent (UV/VIS Spectroscopy)

water

Lynch, Daniel E.; Cox, Martin J.; King, Patrick M.; Smith, Graham; Journal of Photochemistry and Photobiology A: Chemistry; vol. 324; (2016); p. 87 - 95, View in Reaxys 3 of 18

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

water; dimethyl sulfoxide

Lynch, Daniel E.; Cox, Martin; Smith, Graham; Dyes and Pigments; vol. 121; (2015); p. 385 - 393, View in Reaxys 4 of 18

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

acetonitrile; H2O

Comment (UV/VIS Spectroscopy)

Ratio of solvents: 70:30 v/v

Ling, Ke-Qing; Li, Wen-Shan; Sayre, Lawrence M.; Journal of the American Chemical Society; vol. 130; nb. 3; (2008); p. 933 - 944, View in Reaxys 5 of 18

Solvent (UV/VIS Spectroscopy)

various solvent(s)

Comment (UV/VIS Spectroscopy)

Remark: in liquid helium

Absorption Maxima (UV/ 286.044 VIS) [nm] Lindinger, Albrecht; Lugovoj, Eugene; Peter Toennies; Vilesov, Andrei F.; Zeitschrift fur Physikalische Chemie; vol. 215; nb. 3; (2001); p. 401 - 416, View in Reaxys 6 of 18

Description (UV/VIS Spectroscopy)

UV two-photon absorption

Comment (UV/VIS Spectroscopy)

gas

Carney, Joel R.; Zwier, Timothy S.; Chemical Physics Letters; vol. 341; nb. 1-2; (2001); p. 77 - 85, View in Reaxys 7 of 18

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

1,2-dichloro-ethane

Comment (UV/VIS Spectroscopy)

200 - 610 nm

Abu-Eittah; Abdou; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 93; nb. 11-12; (1996); p. 1958 - 1973, View in Reaxys 8 of 18

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

aq. KOH; methanol

Absorption Maxima (UV/ 220; 278; 286 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

36308; 5888; 4266

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

gaseous matrix

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Comment (UV/VIS Spectroscopy)

285.5 - 287.5 nm

Pang, Ho Ming; Lubman, David M.; Analytical Chemistry; vol. 61; nb. 7; (1989); p. 777 - 779, View in Reaxys 10 of 18

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

gaseous matrix

Comment (UV/VIS Spectroscopy)

284.5 - 287.5 nm

Li, Liang; Lubman, David M.; Analytical Chemistry; vol. 60; nb. 23; (1988); p. 2591 - 2598, View in Reaxys 11 of 18

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 292; 282; 276; 228 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

4467; 5370; 5129; 33884

Groen, C.; Christophersen, C.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 8; (1984); p. 709 - 712, View in Reaxys 12 of 18

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 292; 284; 276; 228 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

4467; 5370; 5129; 33884

Groen, C.; Christophersen, C.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 8; (1984); p. 709 - 712, View in Reaxys 13 of 18

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

H2O

Absorption Maxima (UV/ 450 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

200

Deetz, J. S.; Behrman, E. J.; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 135 - 140, View in Reaxys 14 of 18

Description (UV/VIS Spectroscopy)

Absorption maxima

Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys; Ramachandran; Witkop; Biochemistry; vol. 3; (1964); p. 1603,1606, View in Reaxys; Jackson; Smith; Journal of the Chemical Society; (1964); p. 5510,5511, View in Reaxys; Gasco; Farmaco, Edizione Scientifica; vol. 30; (1975); p. 512,513, View in Reaxys; Hinman; Lang; Journal of the American Chemical Society; vol. 86; (1964); p. 3796,3797,3804, View in Reaxys 15 of 18

Description (UV/VIS Spectroscopy)

Triplet-triplet band

Bazin et al.; Chemical Physics Letters; vol. 36; (1975); p. 505,506, 507, View in Reaxys 16 of 18

Description (UV/VIS Spectroscopy)

UV/VIS

Mollan et al.; Phytochemistry (Elsevier); vol. 12; (1973); p. 447,448, View in Reaxys; Yagil; Tetrahedron; vol. 23; nb. 6; (1967); p. 2855 - 2861, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New

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York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys; Ghosal; Srivastava; Phytochemistry (Elsevier); vol. 12; (1973); p. 193,196, View in Reaxys 17 of 18

Description (UV/VIS Spectroscopy)

Spectrum

Comment (UV/VIS Spectroscopy)

230 - 390 nm

Hoshino; Tamura; Justus Liebigs Annalen der Chemie; vol. 500; (1933); p. 42,45, View in Reaxys; Claudatus et al.; Archives of Biochemistry; vol. 72; (1957); p. 316,319, View in Reaxys 18 of 18

Description (UV/VIS Spectroscopy)

Absorption maxima

Absorption Maxima (UV/ 222; 276; 282; 291 VIS) [nm] Noland; Hartman; Journal of the American Chemical Society; vol. 76; (1954); p. 3227, View in Reaxys ESR Spectroscopy (1) 1 of 1

Description (ESR Spectroscopy)

Spectrum

Grady et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 2949, View in Reaxys Rotational Spectroscopy (2) Description (Rota- Comment (Rota- References tional Spectrosco- tional Spectroscopy) py) Rotational spectrum

vibrational analysis

Schmitt, Michael; Boehm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo; Journal of the American Chemical Society; vol. 127; nb. 29; (2005); p. 10356 - 10364, View in Reaxys

Rotational spectrum

two conformers

Caminati, Walther; Physical Chemistry Chemical Physics; vol. 6; nb. 10; (2004); p. 2806 - 2809, View in Reaxys

Luminescence Spectroscopy (5) Description (LuComment (Lumiminescence nescence SpecSpectroscopy) troscopy)

References

Luminescence quantum yield

Lasser; Feitelson; Journal of Physical Chemistry; vol. 77; (1973); p. 1011,1015, View in Reaxys; Ricci; Photochemistry and Photobiology; vol. 12; (1970); p. 67,70, View in Reaxys; Szabo, A. G.; Rayner, D. M.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 554 - 563, View in Reaxys; Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys; Arnold, Steven; Tong, Ling; Sulkes, Mark; Journal of Physical Chemistry; vol. 98; nb. 9; (1994); p. 2325 - 2327, View in Reaxys; Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys

Luminescence lifetime

Lasser; Feitelson; Journal of Physical Chemistry; vol. 77; (1973); p. 1011,1015, View in Reaxys; Szabo, A. G.; Rayner, D. M.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 554 - 563, View in Reaxys; Arnold, Steven; Tong, Ling; Sulkes, Mark; Journal of Physical Chemistry; vol. 98; nb. 9; (1994); p. 2325 - 2327, View in Reaxys; Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys

Electroluminescence

Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys

Luminescence quenching

Froehlich; Nelson; Journal of Physical Chemistry; vol. 82; (1978); p. 2401, View in Reaxys; Lasser; Feitelson; Journal of Physical Chemistry; vol. 77; (1973); p. 1011,1015, View in Reaxys; Davidson; Trethewey; Journal of the American Chemical Society; vol. 98; (1976); p. 4008, View in Reaxys; Eftink; Ghiron; Journal of Physical Chemistry; vol. 800; (1976); p. 486,489, View in Reaxys

Luminescence quantum yield

Quantenausbeute White; Biochemical Journal; vol. 71; (1959); p. 217,219, View in Reaxys der Fluorescenz von wss. Loesungen vom pH 7-12.

Fluorescence Spectroscopy (18)

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Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)

Comment (Fluorescence Spectroscopy)

References

Maxima; Spectrum

Meng, Xue; Guo, Wenjuan; Qin, Xiaoli; Liu, Yiming; Zhu, Xiangwei; Pei, Meishan; Wang, Luyan; RSC Advances; vol. 4; nb. 73; (2014); p. 38649 - 38654, View in Reaxys

Fluorescence

Bowman et al.; Science (Washington, DC, United States); vol. 122; (1955); p. 32, View in Reaxys; Kirby; Steiner; Journal of Physical Chemistry; vol. 74; (1970); p. 4480, View in Reaxys; Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys; Roshchupkin et al.; Photochemistry and Photobiology; vol. 30; (1979); p. 635,637, View in Reaxys; Lawaczeck; Berichte der Bunsen-Gesellschaft; vol. 82; (1978); p. 930, View in Reaxys; Abdallah et al.; European Journal of Biochemistry; vol. 89; (1978); p. 397,401, View in Reaxys; Feng, Ke; Kleinermanns, Karl; Chemical Physics Letters; vol. 473; nb. 4-6; (2009); p. 220 - 222, View in Reaxys

Fluorescence excitation spectrum

influence of an electric field. Object(s) of Study: vapour

Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys

Fluorescence excitation spectrum

vapour

Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys

Maxima

vapour

Fluorescence quantum yield

Guzow, Katarzyna; Szabelski, Mariusz; Rzeska, Alicja; Karolczak, Jerzy; Sulowska, Hanna; Wiczk, Wieslaw; Chemical Physics Letters; vol. 362; nb. 5-6; (2002); p. 519 - 526, View in Reaxys

Spectrum

various solvent(s)

low temperature. Object(s) of Study: various conformers

Lindinger, Albrecht; Lugovoj, Eugene; Peter Toennies; Vilesov, Andrei F.; Zeitschrift fur Physikalische Chemie; vol. 215; nb. 3; (2001); p. 401 - 416, View in Reaxys

Maxima

various solvent(s)

low temperature. Object(s) of Study: various conformers

Lindinger, Albrecht; Lugovoj, Eugene; Peter Toennies; Vilesov, Andrei F.; Zeitschrift fur Physikalische Chemie; vol. 215; nb. 3; (2001); p. 401 - 416, View in Reaxys

Fluorescence excitation spectrum; Spectrum

Piuzzi, Francois; Dimicoli, Iliana; Mons, Michel; Tardivel, Benjamin; Zhao, Qingchun; Chemical Physics Letters; vol. 320; nb. 3-4; (2000); p. 282 - 288, View in Reaxys

Maxima

H2O

363 nm

Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys

Spectrum

methanol

300 - 450 nm

Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys

Spectrum

various solvent(s)

300 - 450 nm

Maxima

aq. KOH; methanol

361 nm

Maxima

various solvent(s)

346 nm

Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Includ-

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ing Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys Maxima

methanol

352 nm

Spectrum

CHCl3

294.12 - 285.71 nm

Peteanu, Linda A.; Levy, Donald H.; Journal of Physical Chemistry; vol. 92; nb. 23; (1988); p. 6554 - 6561, View in Reaxys

Spectrum

287.36 - 278.55 nm

Park, Young D.; Rizzo, Thomas R.; Peteanu, Linda A.; Levy, Donald H.; Journal of Chemical Physics; vol. 84; nb. 12; (1986); p. 6539 - 6549, View in Reaxys

Maxima

Intensitaet der Fluorescenz von wss. Loesungen vom pH 1-7.

White; Biochemical Journal; vol. 71; (1959); p. 217,219, View in Reaxys

Phosphorescence Spectroscopy (1) Description References (Phosphorescence Spectroscopy) Phosphorescence Svejda et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 7138, View in Reaxys Other Spectroscopic Methods (1) Description (Oth- References er Spectroscopic Methods) Photoelectron spectrum

Domelsmith et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 4311,4315, View in Reaxys

Pharmacological Data (193) 1 of 193

Comment (Pharmacological Data)

Bioactivities present

Culvenor,C.C.J.; Ham,N.S.; Australian Journal of Chemistry; vol. 27; (1974); p. 2191 - 2198, View in Reaxys; Leemann,H.G.; Weller,H.; Helvetica Chimica Acta; vol. 43; (1960); p. 1359 - 1364, View in Reaxys; Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys; Jirkovsky,I.; Protiva,M.; Collection of Czechoslovak Chemical Communications; vol. 32; nb. 3; (1967); p. 1197 - 1209, View in Reaxys; Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English, View in Reaxys; Patent; American Home Products Corporation; US3943148; (1976); (A1) English, View in Reaxys; Konda; Suzuki; Omura; Onda; Chemical and Pharmaceutical Bulletin; vol. 24; nb. 1; (1976); p. 92 - 96, View in Reaxys; Severin; Brautigam; Chemische Berichte; vol. 106; nb. 9; (1973); p. 2943 - 2949, View in Reaxys; Brubacher,L.J.; Bender,M.L.; Journal of the American Chemical Society; vol. 88; (1966); p. 5871 - 5880, View in Reaxys; Patent; BASF Aktiengesellschaft; US4565870; (1986); (A1) English, View in Reaxys; Patent; Eli Lilly and Company; US4614807; (1986); (A1) English, View in Reaxys; MacKellar,F.A. et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 7155 - 7156, View in Reaxys; Patent; Merck Sharp and Dohme Limited; US5298520; (1994); (A1) English, View in Reaxys; Mattes; Hutchinson; Springer; Clardy; Journal of the American Chemical Society; vol. 97; nb. 21; (1975); p. 6270 - 6271, View in Reaxys; Saito,I. et al.; Journal of the American Chemical Society; vol. 97; (1975); p. 7191 - 7193, View in Reaxys; Patent; The Upjohn Company; US5347029; (1994); (A1) English, View in Reaxys; Freter,K. et al.; Justus Liebigs Annalen der Chemie; vol. 684; (1965); p. 159 - 187, View in Reaxys; Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); (A1) English, View in Reaxys; Patent; Kureha Chemical Industry Co., Ltd.; EP1273571; (2003); (A1) English, View in Reaxys; Patent; Nippon Shinyaku Co., Ltd.; EP1275657; (2003); (A1) English, View in Reaxys; Patent; McNeilab, Inc.; US4803218; (1989); (A1) English, View in Reaxys; Patent; Glaxo Group Limited; US4816470; (1989); (A1) English, View in Reaxys; Patent; Glaxo Group Limited; US4833153; (1989); (A1) English, View in Reaxys; Patent; Richter Gedeon Vegyeszeti Gyar Rt.; US4843080; (1989); (A1) English, View in Reaxys; Patent; Pfizer Inc.; US4861891; (1989); (A1) English, View in Reaxys; Bergman,J. et al.; Tetrahedron; vol. 29; (1973); p. 971 - 976, View in Reaxys; Patent; Nisshin Flour Milling Co., Ltd.; US5736550; (1998); (A1) English, View in Reaxys; Patent; Merck and Co., Inc.; US5756507; (1998); (A1) English, View in Reaxys; Pfeil,E.; Harder,U.; Angewandte Chemie; vol. 79; (1967); p. 188, View in Reaxys; Patent; Merck and Co., Inc.; US5849764; (1998); (A1) English, View in Reaxys; Patent; Roussel Uclaf; US4904655; (1990); (A1) English, View in Reaxys; Patent; Bayer Aktiengesellschaft; US5015657; (1991); (A1) English, View in Reaxys; Larrouquere,J.; Bulletin de la Societe Chimique de France; nb. 1; (1968); p. 329 335, View in Reaxys; Blackstock,W.P. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 910 - 911, View in Reaxys; Battersby,A.R. et al.; Chemical Communications (London); (1968); p. 1282 - 1284, View in Reaxys; Patent; Schmitz, Robert A.; US6299892; (2001); (B1) English, View in Reaxys; Patent; Sankyo Company, Limited; US6329405; (2001); (B1) English, View in Reaxys; Patent; Syntex (U.S.A.) Inc.; US5436264; (1995); (A1) English, View in Reaxys; Patent; Synaptic Pharmaceutical Corporation; US5476782; (1995); (A1) English, View in Reaxys; Patent; G. D. Searle and Co.; US5530018; (1996); (A1) English,

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View in Reaxys; Arya,V.P.; Indian Journal of Chemistry; vol. 13; (1975); p. 1262 - 1266, View in Reaxys; Patent; Merck Sharp and Dohme Ltd.; US6140347; (2000); (A1) English, View in Reaxys; Patent; Pharmacia and Upjohn Company; US6150385; (2000); (A1) English, View in Reaxys; Takano,S. et al.; Journal of the Chemical Society, Chemical Communications; (1977); p. 68, View in Reaxys; Patent; Sankyo Company, Limited; US5877199; (1999); (A1) English, View in Reaxys; Brown,R.T. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1976); p. 160 - 162, View in Reaxys; Fleming,I.; Woolias,M.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 829 - 837, View in Reaxys; Kametani,T. et al.; Journal of Heterocyclic Chemistry; vol. 5; (1968); p. 799 - 804, View in Reaxys; Patent; Novo Nordisk A/S; US5126363; (1992); (A1) English, View in Reaxys; McCormick,D.B.; Journal of Heterocyclic Chemistry; vol. 10; (1973); p. 235 - 237, View in Reaxys; Patent; Sui, Zhihua; Macielag, Mark J.; Guan, Jihua; Jiang, Weiqin; Lanter, James C.; US2002/10183; (2002); (A1) English, View in Reaxys; Patent; Sibley, David R.; Monsma JR., Frederick J.; Hamblin, Mark; US2002/91235; (2002); (A1) English, View in Reaxys; Winn,M.; Zaugg,H.E.; Journal of Organic Chemistry; vol. 33; nb. 10; (1968); p. 3779 - 3783, View in Reaxys; Kametani,T. et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2542 - 2545, View in Reaxys; Battersby,A.R. et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 1193 - 1200, View in Reaxys; Jeffreys,J.A.D.; Journal of the Chemical Society [Section] C: Organic; (1970); p. 1091 - 1103, View in Reaxys; Patent; Aventis Pharmaceuticals Inc.; US6413974; (2002); (B1) English, View in Reaxys; Stoeckigt,J.; Phytochemistry (Elsevier); vol. 18; (1979); p. 965 - 971, View in Reaxys; de Groot,S.; Strating,J.; Recueil des Travaux Chimiques des Pays-Bas; vol. 80; (1961); p. 121 - 133, View in Reaxys; Patent; Chung, John Y. 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D.; Organic Letters; vol. 18; nb. 5; (2016); p. 1198 - 1201, View in Reaxys; Li, Jun; Li, Jianzu; Xu, Yuan; Wang, Yunjie; Zhang, Luyong; Ding, Li; Xuan, Yining; Pang, Tao; Lin, Hansen; Natural Product Research; vol. 30; nb. 7; (2016); p. 800 - 805, View in Reaxys; Bertamino, Alessia; Ostacolo, Carmine; Ambrosino, Paolo; Musella, Simona; Di Sarno, Veronica; Ciaglia, Tania; Soldovieri, Maria Virginia; Iraci, Nunzio; Fernandez Carvajal, Asia; De La Torre-Martinez, Roberto; Ferrer-Montiel, Antonio; Gonzalez Muniz, Rosario; Novellino, Ettore; Taglialatela, Maurizio; Campiglia, Pietro; Gomez-Monterrey, Isabel; Journal of Medicinal Chemistry; vol. 59; nb. 5; (2016); p. 2179 2191, View in Reaxys; Suja, Thachapully D.; Divya; Naik, Lakshma V.; Ravi Kumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 8; (2016); p. 2072 - 2076, View in Reaxys; Lai, Bingbing; Huang, Zhipeng; Jia, Zhifang; Bai, Rongxian; Gu, Yanlong; Catalysis Science and Technology; vol. 6; nb. 6; (2016); p. 1810 - 1820, View in Reaxys; Lynch, Daniel E.; Cox, Martin J.; King, Patrick M.; Smith, Graham; Journal of Photochemistry and Photobiology A: Chemistry; vol. 324; (2016); p. 87 - 95, View in Reaxys; Muscia, Gisela C.; De Mara, Leonardo O.; Buldain, Graciela Y.; Ass, Silvia E.; Journal of Heterocyclic Chemistry; vol. 53; nb. 2; (2016); p. 647 - 650, View in Reaxys; Singh, Thokchom Prasanta; Singh, Okram Mukherjee; Journal of Chemical Sciences; vol. 128; nb. 4; (2016); p. 565 - 572, View in Reaxys; Okada, Masashi; Mei, Zhen-Wu; Imran Hossain, Md.; Wang, Li; Tominaga, Taihei; Takebayashi, Takeshi; Murakami, Masaharu; Yasuda, Mizuki; Shigehiro, Tsukasa; Kasai, Tomonari; Mizutani, Akifumi; Murakami, Hiroshi; El Sayed, Ibrahim El Tantawy; Dan, Shingo; Yamori, Takao; Seno, Masaharu; Inokuchi, Tsutomu; Medicinal Chemistry Research; vol. 25; nb. 5; (2016); p. 879 892, View in Reaxys; brnyi-Balogh, Pter; Földesi, Tams; Grün, Alajos; Volk, Balzs; Keglevich, György; Milen, Mtys; Tetrahedron Letters; vol. 57; nb. 18; (2016); p. 1953 - 1957, View in Reaxys; Deldaele, Christopher; Evano, Gwilherm; ChemCatChem; vol. 8; nb. 7; (2016); p. 1319 - 1328, View in Reaxys; Filipponi, Paolo; Baxendale, Ian

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R.; European Journal of Organic Chemistry; vol. 2016; nb. 11; (2016); p. 2000 - 2012, View in Reaxys; Wehle, Sarah; Espargar, Alba; Sabat, Raimon; Decker, Michael; Tetrahedron; vol. 72; nb. 20; (2016); p. 2535 - 2543, View in Reaxys; Dine, Tharwat Mohy El; Evans, David; Rouden, Jacques; Blanchet, Jrme; Chemistry - A European Journal; vol. 22; nb. 17; (2016); p. 5894 - 5898, View in Reaxys; Patent; UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLER-UNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER, Gerhard; (257 pag.); WO2016/20369; (2016); (A1) English, View in Reaxys; Knouse, Kyle W.; Wuest, William M.; Journal of Antibiotics; vol. 69; nb. 4; (2016); p. 337 - 339, View in Reaxys; Zheng, Nan; Chang, YuanYuan; Zhang, Li-Jie; Gong, Jian-Xian; Yang, Zhen; Chemistry - An Asian Journal; vol. 11; nb. 3; (2016); p. 371 375, View in Reaxys; Devaraj; Sollert; Juds; Gates; Pilarski; Chemical Communications; vol. 52; nb. 34; (2016); p. 5868 - 5871, View in Reaxys; Subba Reddy; Reddy; Siriwardena; Organic and Biomolecular Chemistry; vol. 14; nb. 18; (2016); p. 4276 - 4282, View in Reaxys; Abhishek A. Kulkarni; Amol M. Pachpinde; Devanand B. Shinde; Firoz A. Kalam Khan; Jaiprakash N. Sangshetti; Kishan S. Lohar; Rajendra H. Patil; Bioorganic & medicinal chemistry letters; vol. 26; (2016); p. 829 - 835, View in Reaxys 2 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Hosaka, Shinya; Murayama, Norie; Satsukawa, Masahiro; Shimizu, Makiko; Uehara, Shotaro; Fujino, Hideki; Iwasaki, Kazuhide; Iwano, Shunsuke; Uno, Yasuhiro; Yamazaki, Hiroshi; Drug Metabolism and Disposition; vol. 43; nb. 1; (2015); p. 27 - 33, View in Reaxys 3 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Henrottin, Jean; Zervosen, Astrid; Lemaire, Christian; Sapunaric, Frdric; Laurent, Sophie; Van Den Eynde, Benoit; Goldman, Serge; Plenevaux, Alain; Luxen, Andr; ACS Medicinal Chemistry Letters; vol. 6; nb. 3; (2015); p. 260 - 265, View in Reaxys 4 of 193

Location

Paragraph

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; THE BOARD OF REGENTS OF THE NEVADA SYSTEM OF HIGHER EDUCATION ON BEHALF OF THE UNIVERSITY; Abel-Santos, Ernesto; US2015/173357; (2015); (A1) English, View in Reaxys 5 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Shaala, Lamiaa A.; Youssef, Diaa T. A.; Marine Drugs; vol. 13; nb. 4; (2015); p. 1698 - 1709, View in Reaxys 6 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Comment (Pharmacological Data)

physiological behaviour discussed

Chapy, Hlne; Goracci, Laura; Vayer, Philippe; Parmentier, Yannick; Carrupt, Pierre-Alain; Declves, Xavier; Scherrmann, Jean-Michel; Cisternino, Salvatore; Cruciani, Gabriele; British Journal of Pharmacology; vol. 172; nb. 20; (2015); p. 4888 - 4904, View in Reaxys 8 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Cheng, Yating; Jin, Un-Ho; Allred, Clint D.; Jayaraman, Arul; Chapkin, Robert S.; Safe, Stephen; Drug Metabolism and Disposition; vol. 43; nb. 10; (2015); p. 1536 - 1543, View in Reaxys 9 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Liu, Changlu; Bonaventure, Pascal; Lee, Grace; Nepomuceno, Diane; Kuei, Chester; Wu, Jiejun; Li, Qingqin; Joseph, Victory; Sutton, Steven W.; Eckert, William; Yao, Xiang; Yieh, Lynn; Dvorak, Curt; Carruthers, Nicholas; Coate, Heather; Yun, Sujin; Dugovic, Christine; Harrington, Anthony; Lovenberg, Timothy W.; Molecular Pharmacology; vol. 88; nb. 5; (2015); p. 911 - 925, View in Reaxys 10 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Herington, Jennifer L.; Swale, Daniel R.; Brown, Naoko; Shelton, Elaine L.; Choi, Hyehun; Williams, Charles H.; Hong, Charles C.; Paria, Bibhash C.; Denton, Jerod S.; Reese, Jeff; PLoS ONE; vol. 10; nb. 11; (2015); Art.No: E0143243, View in Reaxys

89/155

2016-06-21 14:42:30

11 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Jin, Un-Ho; Lee, Syng-Ook; Sridharan, Gautham; Lee, Kyongbum; Davidson, Laurie A.; Jayaraman, Arul; Chapkin, Robert S.; Alaniz, Robert; Safe, Stephen; Molecular Pharmacology; vol. 85; nb. 5; (2014); p. 777 - 788, View in Reaxys 12 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Oliveira, Rafael R.B.; Brito, Thaysnara B.; Nepel, Angelita; Costa, Emmanoel V.; Barison, Andersson; Nunes, Rogeria S.; Santos, Roseli L.C.; Cavalcanti, Socrates C.H.; Medicinal Chemistry; vol. 10; nb. 6; (2014); p. 580 587, View in Reaxys 13 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys 14 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Toy, Nurten; Özogul, Fatih; Özogul, Yesim; Food Chemistry; vol. 173; (2014); p. 45 - 53, View in Reaxys 15 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Luetje, Charles W.; Chen, Sisi; F1000Research; vol. 3; (2014), View in Reaxys 16 of 193

Effect (Pharmacological Data)

receptor; activation of

Species or Test-System (Pharmacological Data)

HEK293TGα16gust44 cells of human; genetically modified/infected with: human taste 2 receptor 39

Concentration (Pharmacological Data)

<= 0.03 mmol/l

Method (Pharmacological Data)

name of assay/method: spectrofluorometric assay using calcium-sensitive dye Fluo-4-AM

Further Details (Pharmacological Data)

HEK293TGα16gust44: HEK293T embryonic kidney cells stably expressing the chimeric G-protein α-subunit Gα16-Gust44;

Results

no effect (related to human taste 2 receptor 39)

Kohl, Susann; Behrens, Maik; Dunkel, Andreas; Hofmann, Thomas; Meyerhof, Wolfgang; Journal of Agricultural and Food Chemistry; vol. 61; nb. 1; (2013); p. 53 - 60, View in Reaxys 17 of 193

Effect (Pharmacological Data)

receptor; activation of

Species or Test-System (Pharmacological Data)

HEK293TGα16gust44 cells of human; genetically modified/infected with: human taste 2 receptor 4

Concentration (Pharmacological Data)

<= 0.03 mmol/l

Method (Pharmacological Data)

name of assay/method: spectrofluorometric assay using calcium-sensitive dye Fluo-4-AM

Further Details (Pharmacological Data)

HEK293TGα16gust44: HEK293T embryonic kidney cells stably expressing the chimeric G-protein α-subunit Gα16-Gust44;

Results

no effect (related to human taste 2 receptor 4)

Kohl, Susann; Behrens, Maik; Dunkel, Andreas; Hofmann, Thomas; Meyerhof, Wolfgang; Journal of Agricultural and Food Chemistry; vol. 61; nb. 1; (2013); p. 53 - 60, View in Reaxys 18 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

Broadley, Kenneth J.; Fehler, Martina; Ford, William R.; Kidd, Emma J.; European Journal of Pharmacology; vol. 715; nb. 1-3; (2013); p. 370 - 380, View in Reaxys 19 of 193

Comment (Pharmacological Data)

physiological behaviour discussed

90/155

2016-06-21 14:42:30

Effect (Pharmacological Data)

butyl-induced enzyme activity; effect on

Species or Test-System (Pharmacological Data)

Rhodococcus opacus DSM 43250

Results

molecular target: amino oxidase

Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 21 of 193

Effect (Pharmacological Data)

butyl-induced enzyme activity; effect on

Species or Test-System (Pharmacological Data)

Rhodococcus opacus DSM 43250

Type (Pharmacological Data)

activity rate

Value of Type (Pharmacological Data)

18 percent

Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 22 of 193

Effect (Pharmacological Data)

methylamine-induced enzyme activity; effect on

Species or Test-System (Pharmacological Data)

Rhodococcus opacus DSM 43250

Results

molecular target: amino oxidase

Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 23 of 193

Effect (Pharmacological Data)

methylamine-induced enzyme activity; effect on

Species or Test-System (Pharmacological Data)

Rhodococcus opacus DSM 43250

Type (Pharmacological Data)

activity rate

Value of Type (Pharmacological Data)

29 percent

Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 24 of 193

Effect (Pharmacological Data)

phenylethylamine-induced enzyme activity; effect on

Species or Test-System (Pharmacological Data)

Rhodococcus opacus DSM 43250

Results

molecular target: amino oxidase

Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 25 of 193

Effect (Pharmacological Data)

phenylethylamine-induced enzyme activity; effect on

Species or Test-System (Pharmacological Data)

Rhodococcus opacus DSM 43250

Type (Pharmacological Data)

activity rate

Value of Type (Pharmacological Data)

85 percent

91/155

2016-06-21 14:42:30

Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 26 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

brain membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

in presence of 30 μmol/l spermine; radioligand binding assay ; radioligand: [3H]MK-801

Results

molecular target: NMDA receptor

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 27 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

brain membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

in presence of 30 μmol/l spermine; radioligand binding assay ; radioligand: [3H]MK-801; IC50 related to: NMDA receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

484 μmol/l

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 28 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

brain membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

radioligand binding assay; radioligand: [3H]MK-801

Results

molecular target: NMDA receptor

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 29 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

brain membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

radioligand binding assay; radioligand: [3H]MK-801; IC50 related to: NMDA receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

85 μmol/l

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 30 of 193

Effect (Pharmacological Data)

receptor binding affinity

92/155

2016-06-21 14:42:30

Species or Test-System (Pharmacological Data)

hippocampal CA1 + dentate gyrus membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

radioligand binding assay; radioligand: [3H]-OH-DPAT

Results

molecular target: 5-HT1A receptor

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 31 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

hippocampal CA1 + dentate gyrus membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

radioligand binding assay; radioligand: [3H]-OH-DPAT; IC50 related to: 5-HT1A receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.33 μmol/l

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 32 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

prefrontal cortex membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

radioligand binding assay; radioligand: [3H]ketanserin

Results

molecular target: 5-HT2A receptor

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 33 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

prefrontal cortex membranes of Wistar rat

Sex

male

Further Details (Pharmacological Data)

radioligand binding assay; radioligand: [3H]ketanserin; IC50 related to: 5-HT2A receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

16.3 μmol/l

Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 34 of 193

Effect (Pharmacological Data)

antifungal

Species or Test-System (Pharmacological Data)

Leptosphaeria maculans

Concentration (Pharmacological Data)

0.1 - 0.5 mmol/l

93/155

2016-06-21 14:42:30

Kind of Dosing (Pharmacological Data)

title comp. dissolved in CH3CN

Further Details (Pharmacological Data)

mycelial radial growth bioassay

Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

12 - 28 percent

Pedras, M. Soledade C.; Sarma-Mamillapalle, Vijay K.; Journal of Agricultural and Food Chemistry; vol. 60; nb. 32; (2012); p. 7792 - 7798, View in Reaxys 35 of 193

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

recombinant CYP2A13 of human

Further Details (Pharmacological Data)

substrate: p-nitrophenol; CYP2A13: cytochrome P450-2A13

Results

molecular target: CYP2A13; species of target: human

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 36 of 193

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

recombinant CYP2A13 of human

Further Details (Pharmacological Data)

substrate: p-nitrophenol; CYP2A13: cytochrome P450-2A13; inhibition constant (ki)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

16 μmol/l

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 37 of 193

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

recombinant CYP2A6 of human

Further Details (Pharmacological Data)

substrate: p-nitrophenol; CYP2A6: cytochrome P450-2A6

Results

molecular target: CYP2A6; species of target: human

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 38 of 193

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

recombinant CYP2A6 of human

Further Details (Pharmacological Data)

substrate: p-nitrophenol; CYP2A6: cytochrome P450-2A6; inhibition constant (ki)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.7 μmol/l

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys

94/155

2016-06-21 14:42:30

39 of 193

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

recombinant CYP2A13 of human

Method (Pharmacological Data)

name of assay/method: spectrophotometry

Further Details (Pharmacological Data)

CYP2A13: cytochrome P450-2A13

Results

molecular target: CYP2A13; species of target: human

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 40 of 193

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

recombinant CYP2A13 of human

Method (Pharmacological Data)

name of assay/method: spectrophotometry

Further Details (Pharmacological Data)

CYP2A13: cytochrome P450-2A13; equilibrium dissociation constant (kd)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

5.2 μmol/l

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 41 of 193

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

recombinant CYP2A6 of human

Method (Pharmacological Data)

name of assay/method: spectrophotometry

Further Details (Pharmacological Data)

CYP2A6: cytochrome P450-2A6

Results

molecular target: CYP2A6; species of target: human

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 42 of 193

Effect (Pharmacological Data)

protein binding affinity

Species or Test-System (Pharmacological Data)

recombinant CYP2A6 of human

Method (Pharmacological Data)

name of assay/method: spectrophotometry

Further Details (Pharmacological Data)

CYP2A6: cytochrome P450-2A6; equilibrium dissociation constant (kd)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.3 μmol/l

Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 43 of 193

Effect (Pharmacological Data)

protein binding

95/155

2016-06-21 14:42:30

Species or Test-System (Pharmacological Data)

AANAT2 of sea bream

Further Details (Pharmacological Data)

AANAT: arylalkylamine N-acetyltransferase

Results

molecular target: AANAT2

Zilberman-Peled, Bina; Bransburg-Zabary, Sharron; Klein, David C.; Gothilf, Yoav; Marine Drugs; vol. 9; nb. 5; (2011); p. 906 - 921, View in Reaxys 44 of 193

Effect (Pharmacological Data)

L-Proline uptake; inhibition of

Species or Test-System (Pharmacological Data)

oocyte of Xenopus laevis, frog; genetically modified/infected with: rat PAT2

Concentration (Pharmacological Data)

10 mmol/l

Further Details (Pharmacological Data)

PAT2 (SLC36A2): H+-coupled amino acid transporter; radiolabel (L-[3H]Proline) flux assay

Results

no effect

Edwards, Noel; Anderson, Catriona M.H.; Gatfield, Kelly M.; Jevons, Mark P.; Ganapathy, Vadivel; Thwaites, David T.; Biochimica et Biophysica Acta - Biomembranes; vol. 1808; nb. 1; (2011); p. 260 - 270, View in Reaxys 45 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-S3.36A receptor DNA mixed with 33 μL lipofectamine 2000 reagent

Further Details (Pharmacological Data)

competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM

Results

molecular target: human 5-HT2C-S3.36A receptor

Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 46 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-S3.36A receptor DNA mixed with 33 μL lipofectamine 2000 reagent

Further Details (Pharmacological Data)

competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM; Ki related to: human 5-HT2C-S3.36A receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1513 nmol/l

Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 47 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-Y7.43A receptor DNA mixed with 33 μL lipofectamine 2000 reagent

Further Details (Pharmacological Data)

competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM

Results

molecular target: human 5-HT2C-Y7.43A receptor

Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 48 of 193

Effect (Pharmacological Data)

receptor binding affinity

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Species or Test-System (Pharmacological Data)

HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-Y7.43A receptor DNA mixed with 33 μL lipofectamine 2000 reagent

Further Details (Pharmacological Data)

competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM; Ki related to: human 5-HT2C-Y7.43A receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

298.5 nmol/l

Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 49 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

HEK-293 cells membranes; genetically modified/infected with: human 5-HT2C receptor DNA mixed with 33 μL lipofectamine 2000 reagent

Further Details (Pharmacological Data)

competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM

Results

molecular target: human 5-HT2C receptor

Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 50 of 193

Effect (Pharmacological Data)

receptor binding affinity

Species or Test-System (Pharmacological Data)

HEK-293 cells membranes; genetically modified/infected with: human 5-HT2C receptor DNA mixed with 33 μL lipofectamine 2000 reagent

Further Details (Pharmacological Data)

competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM; Ki related to: human 5-HT2C receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

57.1 nmol/l

Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 51 of 193

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

bovine pancreatic trypsin

Kind of Dosing (Pharmacological Data)

title comp. in DMSO

Further Details (Pharmacological Data)

fluorescence-based inhibition assay

Results

molecular target: bovine pancreatic trypsin

Yamane, Junji; Yao, Min; Zhou, Yong; Hiramatsu, Yasuyuki; Fujiwara, Kenichiro; Yamaguchi, Tohru; Yamaguchi, Hiroto; Togame, Hiroko; Tsujishita, Hideki; Takemoto, Hiroshi; Tanaka, Isao; Journal of Applied Crystallography; vol. 44; nb. 4; (2011); p. 798 - 804, View in Reaxys 52 of 193

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

bovine pancreatic trypsin

Kind of Dosing (Pharmacological Data)

title comp. in DMSO

Further Details (Pharmacological Data)

fluorescence-based inhibition assay; inhibitory concentration (IC)

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

873 μmol/l

Effect (Pharmacological Data)

sigma-1 receptor; binding to

Species or Test-System (Pharmacological Data)

liver membrane homogenate

Method (Pharmacological Data)

Competition assays against the sigma-1 receptor specific ligand, (+)- [3H] -pentazocine (10 nM) determined that the non-methylated trace amines tryptamine, phenethylamine, and tyramine bound the sigma-1 receptor poorly (Table 4), with Kd values of 431.55 μM, 97.4 μM, and >30000 μM, respectively. By contrast, the iV-methylated and iV,./V-dimethylated derivatives of these compounds bound sigma-1 receptors more tightly, with a clear increase in affinity as the ligands approached the sigma-1 receptor ligand pharmacophore (Figures 5a and 5b). With the exception of the iV-methylated tyramines, this trend did not apply to the sigma-2 receptor, which differs pharmacologically and functionally from the sigma-1 receptor (Table 4).Tryptamine, phenethylamine, and iV-methyltyramine, had the highest sigma-2 receptor affinities with Kd values of 4.91 μM, 7.31 μM, and 6.61 μM, respectively. In contrast to sigma-1 receptors, iV-methylation and ΛζiV-dimethylation of tryptamine and phenethylamine decreased sigma- 2 receptor affinity (Table 4).; Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Sigma Receptor Binding Assays. Competitive binding assays were performed as previously described (18) with the exception of testing new ligands shown in Table 4.

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

431.55 μmol/l

Location

Page/Page column 29-30; 34-35

Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 54 of 193

Effect (Pharmacological Data)

sigma-2 receptor; binding to

Species or Test-System (Pharmacological Data)

liver membrane homogenate

Method (Pharmacological Data)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.91 μmol/l

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Location

Page/Page column 29-30; 34-35

Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 55 of 193

Effect (Pharmacological Data)

sigma-1 receptor photolabeling; inhibition of

Species or Test-System (Pharmacological Data)

liver membranes photolabelled with 3-[125I]iodo-4-azidococaine of rat

Method (Pharmacological Data)

The ability of tryptamine, iV-methyltryptamine, and DMT to block sigma receptor photolabeling in rat liver homogenates were tested by two radioactive photoaffinity labels, the sigma-1 receptor specific cocaine derivative 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) (Figure 6a), and the sigma-1 and sigma-2 receptor fenpropimorph derivative l-N-(2',6'-dimethyl- morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) (Figure 6b). Both of these compounds have been used to identify the drug binding region of the sigma-1 receptor (18, 19). [125I]-IACoC (sigma-1 Kd = 0.126 nM(l 7)) photolabeling of the 26 kDa sigma-1 receptor (Figure 6a) was protected best by DMT, with 61percent protection by 50 μM DMT and almost 100percent protection by 100 μM DMT. On the other hand, tryptamine and iV-methyltryptamine protected minimally against sigma-1 receptor [125I]-IACoC photolabeling, even at these high concentrations (Figure 6a). Similarly, [125I]IAF photolabeling of the sigma-1 (Kd = 194 nM (18)) receptor showed that DMT was the most potent protector. Ten μM DMT protected 31percent, while 50 μM and 100 μM DMT protected 43percent and 69percent, respectively (Figure 6b). With the exception of iV-methyltryptamine, protection of [125I]IAF sigma-2 (Kd = 2780 nM(iS)) receptor photolabeling paralleled the sigma-2 binding data. Tryptamine afforded the greatest protection of sigma-2 receptor photolabeling, with values of 47percent, 78percent, and 79percent for 10, 50, and 100 μM, respectively (Figure 6b).; Radiochemistry. Radiosynthesis of 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) and 1-N- (2',6'dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) was performed as described. Preparation of Rat/Guinea Pig/Mouse Liver membranes. Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Photoaffinity Labeling. Sigma- 1 and sigma-2 receptors were photolabeled with 3-[125I]iodo- 4-azidococaine ([125I]-IACoC) and l-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) as described (18) with the exception of the protecting ligands, tryptamine, N- methyltryptamine, and iV,./V-dimethyltryptamine (DMT).

Results

band intensity sigma-1 (percent) = 111, 74 and 81 at a concentration of 10, 50 and 100 μmol/l, respectively

Location

Page/Page column 30; 34-35; 7/12

Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 56 of 193

Effect (Pharmacological Data)

sigma-1 receptor photolabeling; inhibition of

Species or Test-System (Pharmacological Data)

liver membranes photolabelled with 1-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodophenyl)propane of rat

Method (Pharmacological Data)

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respectively (Figure 6b).; Radiochemistry. Radiosynthesis of 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) and 1-N- (2',6'dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) was performed as described. Preparation of Rat/Guinea Pig/Mouse Liver membranes. Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Photoaffinity Labeling. Sigma- 1 and sigma-2 receptors were photolabeled with 3-[125I]iodo- 4-azidococaine ([125I]-IACoC) and l-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) as described (18) with the exception of the protecting ligands, tryptamine, N- methyltryptamine, and iV,./V-dimethyltryptamine (DMT). Results

band intensity sigma-1 (percent) = 100, 81 and 65 at a concentration of 10, 50 and 100 μmol/l, respectively

Location

Page/Page column 30; 34-35; 7/12

Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 57 of 193

Effect (Pharmacological Data)

sigma-2 receptor photolabeling; inhibition of

Species or Test-System (Pharmacological Data)

liver membranes photolabelled with 1-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodophenyl)propane of rat

Method (Pharmacological Data)

Results

band intensity sigma-2 (percent) = 53, 22 and 21 at a concentration of 10, 50 and 100 μmol/l, respectively

Location

Page/Page column 30; 34-35; 7/12

Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 58 of 193

Effect (Pharmacological Data)

buds/plant thinning

Species or Test-System (Pharmacological Data)

chrysanthemum, cv Herby Mixed

Method (Pharmacological Data)

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randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees F at night.Sowing Date: 5 October 2009, in plugs. Application Date: 2 December 2009 (first bud). Measurement Date: 12 January 2010 (flowering). Measurement: Number of buds per plant.A number of auxins or auxin precursors were applied, each at 10"2 Molar solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test.Application of an auxin or auxin precursor resulted in a reduced mean number of buds per plant, as expected from an effective thinning agent. Application of AC in addition to an auxin or auxin precursor resulted in further reduction in mean number of buds per plant. Results

improvement over control (percent) = +0.0

Location

Page/Page column 25-26

Comment (Pharmacological Data)

potential area of application: agro

Metabolite XRN (Pharmacological Data)

143358; 121586; 125488; 474217; 1528281; 20752795

Metabolite (Pharmacological Data)

indole-3-acetic acid; indole-3-acetaldehyde; indole-3-acetonitrile; N-Hydroxytryptamine; (Z/E)-3-Indolylacetaldoxime; C10H10N2O2

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; DECKERS, Tom; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116256; (2010); (A2) English, View in Reaxys 59 of 193

Effect (Pharmacological Data)

buds/plant thinning

Species or Test-System (Pharmacological Data)

chrysanthemum, cv Herby Mixed

Method (Pharmacological Data)

EXAMPLE 2 - CHRYSANTHEMUM - cv Herby MixedA. To demonstrate the benefits to flower bud thinning of applying an auxin/auxin precursor or auxin/auxin precursor plus acetaminophen.Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees F at night.Sowing Date: 5 October 2009, in plugs. Application Date: 2 December 2009 (first bud). Measurement Date: 12 January 2010 (flowering). Measurement: Number of buds per plant.A number of auxins or auxin precursors were applied, each at 10"2 Molar solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test.Application of an auxin or auxin precursor resulted in a reduced mean number of buds per plant, as expected from an effective thinning agent. Application of AC in addition to an auxin or auxin precursor resulted in further reduction in mean number of buds per plant.

Results

mean number of buds/plant = 2.7

Location

Page/Page column 25-26

Comment (Pharmacological Data)

potential area of application: agro

Metabolite XRN (Pharmacological Data)

143358; 121586; 125488; 474217; 1528281; 20752795

Metabolite (Pharmacological Data)

indole-3-acetic acid; indole-3-acetaldehyde; indole-3-acetonitrile; N-Hydroxytryptamine; (Z/E)-3-Indolylacetaldoxime; C10H10N2O2

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; DECKERS, Tom; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116256; (2010); (A2) English, View in Reaxys 60 of 193

Effect (Pharmacological Data)

Petal abscission; delaying of

Species or Test-System (Pharmacological Data)

Papaver nudicale Iceland Poppy

Method (Pharmacological Data)

1. PAPAVER Nudicaule (Iceland Poppy)Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees at night.Sowing Date: 18 November 2009, in plugs. Application Date: 5 January 2010. Measurement Date: 12 January 2010 at daily intervals.A number of auxins or auxin precursors were applied, each at 10"2 Molar

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solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test. Measurement: Delay of first petal fall for each treatment (in days).Petal abscission is delayed by the application of an auxin/auxin precursor. Petal abscission is further delayed by the application of an auxin/auxin precursor plus acetaminophen. Thus, flower longevity is benefited. Results

Improvement (percent) = 19.4 at a dose 0.01 mol/l

Location

Page/Page column 35-36

Comment (Pharmacological Data)

potential area of application: agro

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard, Henry; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116263; (2010); (A2) English, View in Reaxys 61 of 193

Effect (Pharmacological Data)

shelf-life; improvement of

Species or Test-System (Pharmacological Data)

radish - cv F1 Apache

Method (Pharmacological Data)

RADISH - cv F 1 ApacheTo demonstrate the benefits to post-harvest shelf-life from adding an auxin/auxin precursor or auxin/auxin precursor plus acetaminophen.Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees at night.Sowing Date: 3 November 2009, in plugs. Application Dates: 28 December 2009 fb 4 January 2010. Harvest Date: 11 January 2010.Measurement: Shelf-Life (days after harvest) at ambient temperature. A number of auxins or auxin precursors were compared, each at 10"2 Molar solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test.

Results

Shelf-life improvement (percent) = 11.1 at a dose 0.01 mol/l

Location

Page/Page column 38-39

Comment (Pharmacological Data)

potential area of application: agro

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard, Henry; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116263; (2010); (A2) English, View in Reaxys 62 of 193

Effect (Pharmacological Data)

HOCl-induced oxidation; inhibition of

Species or Test-System (Pharmacological Data)

dihydrorhodamine 123

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

6 μmol/l

Estevao, Monica S.; Carvalho, Luisa C.; Ribeiro, Daniela; Couto, Diana; Freitas, Marisa; Gomes, Ana; Ferreira; Fernandes, Eduarda; Marques, M. Manuel B.; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 4869 - 4878, View in Reaxys 63 of 193

Effect (Pharmacological Data)

peroxyl-induced oxidation; inhibition of

Species or Test-System (Pharmacological Data)

fluorescein

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

1.86 μmol/l

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Effect (Pharmacological Data)

NO radical-induced oxidation; inhibition of

Species or Test-System (Pharmacological Data)

4,5-diaminofluorescein

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

672 μmol/l

Effect (Pharmacological Data)

ONOO--induced oxidation; inhibition of

Species or Test-System (Pharmacological Data)

dihydrorhodamine 123

Further Details (Pharmacological Data)

PDP value is dependent on the presence of NaHCO3; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

10.4 - 31.8 μmol/l

Effect (Pharmacological Data)

Species or Test-System (Pharmacological Data)

dihydrorhodamine 123

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

682 μmol/l

2-induced

oxidation; inhibition of

Effect (Pharmacological Data)

nitric oxide formation; inhibition of

Species or Test-System (Pharmacological Data)

cerebellum of Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

1E-05 - 0.01 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in potassium phosphate buffer (pH 7.4)

Further Details (Pharmacological Data)

supernatant of cerebellum homogenate used; mass of species: 120 - 150 g; inhibitory concentration (IC)

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

1.641E-4 mol/l

Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 68 of 193

Effect (Pharmacological Data)

nitric oxide formation; inhibition of

Species or Test-System (Pharmacological Data)

cerebellum of Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

1E-05 - 0.01 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in potassium phosphate buffer (pH 7.4)

Further Details (Pharmacological Data)

supernatant of cerebellum homogenate used; mass of species: 120 - 150 g; inhibitory concentration (IC)

Type (Pharmacological Data)

log IC50

Value of Type (Pharmacological Data)

-3.785

Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 69 of 193

Effect (Pharmacological Data)

nitric oxide formation; inhibition of

Species or Test-System (Pharmacological Data)

cerebellum of Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

1E-05 - 0.01 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in potassium phosphate buffer (pH 7.4)

Further Details (Pharmacological Data)

supernatant of cerebellum homogenate used; mass of species: 120 - 150 g

Type (Pharmacological Data)

maximum inhibition

Value of Type (Pharmacological Data)

23 percent

Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 70 of 193

Effect (Pharmacological Data)

nitric oxide formation; inhibition of

Species or Test-System (Pharmacological Data)

cerebellum of Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

1E-05 - 0.01 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in potassium phosphate buffer (pH 7.4)

Further Details (Pharmacological Data)

supernatant of cerebellum homogenate used; mass of species: 120 - 150 g

Results

molecular target: nitric oxide synthase

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Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 71 of 193

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK293 cells expressing rhesus monkey D2s

Concentration (Pharmacological Data)

1E-09 - 0.0001 mol/l

Method (Pharmacological Data)

cells incub. with title comp. in presence of <3H>dopamine at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>dopamine binding determined

Further Details (Pharmacological Data)

ref.: <3H>dopamine; nonspecific binding was determined in presence of 10 μM raclopride; D2s: dopamine D2 receptor short isoform; HEK: human embryonic kidney

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 10 μmol/l

Results

title comp. had poor binding affinity for D2s relative to dopamine; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 72 of 193

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK293 cells expressing human α2A

Concentration (Pharmacological Data)

1E-10 - 1E-05 mol/l

Method (Pharmacological Data)

cells incub. with title comp. in presence of <3H>norepinephrine at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>norepinephrine binding determined

Further Details (Pharmacological Data)

ref.: <3H>norepinephrine; nonspecific binding was determined in presence of 10 μM SKF86466; HEK: human embryonic kidney; α2A: subtype A of α-adrenal receptor 2

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 10 μmol/l

Results

title comp. had poor binding affinity for α2A relative to norepinephrine; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 73 of 193

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK293 cells expressing human α2B

Concentration (Pharmacological Data)

1E-10 - 1E-05 mol/l

Method (Pharmacological Data)

cells incub. with title comp. in presence of <3H>norepinephrine at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>norepinephrine binding determined

Further Details (Pharmacological Data)

ref.: <3H>norepinephrine; nonspecific binding was determined in presence of 10 μM SKF86466; HEK: human embryonic kidney; α2B: subtype B of α-adrenal receptor 2

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 10 μmol/l

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Results

title comp. had poor binding affinity for α2B relative to norepinephrine; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 74 of 193

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK293 cells expressing 5HT1A

Concentration (Pharmacological Data)

1E-10 - 1E-05 mol/l

Method (Pharmacological Data)

cells incub. with title comp. in presence of <3H>serotonin at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>serotonin binding determined

Further Details (Pharmacological Data)

ref.: <3H>serotonin; nonspecific binding was determined in presence of 10 μM methiothepin; HEK: human embryonic kidney; 5HT1A: subtype A of serotonin receptor 1

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 10 μmol/l

Results

title comp. had poor binding affinity for 5HT1A relative to serotonin; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 75 of 193

Effect (Pharmacological Data)

receptor; activation of

Species or Test-System (Pharmacological Data)

embryonic kidney 293 cells of human

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

cells transfected with rhesus monkey TAAR1 (trace amine-associated receptor) along with CRE-Luc (cAMP-response element-driven luciferase receptor); treated with title comp. for 18 h; CRE-Luc expressed detd. as measure of cAMP accumulation in cells

Further Details (Pharmacological Data)

control: vehicle; further study done in cells expressing rhesus monkey TAAR1 along with autoreceptors D2s (dopamine D2 receptor short isoform), α2A, α2B, 5HT1A or 5HT1B

Results

title comp. activated TAAR1; TAAR1 signaling in response to title comp. was not affected by any of the monoamine autoreceptors tests; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 76 of 193

Effect (Pharmacological Data)

receptor; activation of

Species or Test-System (Pharmacological Data)

embryonic kidney 293 cells of human

Concentration (Pharmacological Data)

1E-08 - 0.0001 mol/l

Method (Pharmacological Data)

cells transfected with rhesus monkey TAAR1 along with CRE-Luc and PGL4.73; treated with title comp. for 18 h; lysed; CRE-Luc expression was determined as measure of cAMP accumulation in cells

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1; CRE-Luc: cAMP-response element-driven luciferase reporter; controls: cells transfected with CRE-Luc and PGL4.73

Results

title comp. increased CRE-Luc expression in a TAAR1-dependent manner; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 77 of 193

Effect (Pharmacological Data)

receptor; binding activity

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Species or Test-System (Pharmacological Data)

HEK293 cells expressing 5HT1B

Concentration (Pharmacological Data)

1E-10 - 1E-05 mol/l

Method (Pharmacological Data)

cells incub. with title comp. in presence of <3H>serotonin at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>serotonin binding determined

Further Details (Pharmacological Data)

ref.: <3H>serotonin; nonspecific binding was determined in presence of 10 μM methiothepin; HEK: human embryonic kidney; 5HT1B: subtype B of serotonin receptor 1

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 10 μmol/l

Results

title comp. had poor binding affinity for 5HT1B relative to serotonin; fig.

Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 78 of 193

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT

Method (Pharmacological Data)

inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.4 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Cys mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.05 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Thr mutant

Method (Pharmacological Data)

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Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.0 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala169Ile mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

7.6 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Thr439Ser mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.83 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Thr439Ala mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.41 μmol/l

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Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Tyr176Phe mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.8 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Tyr175Phe mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.84 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Asp98Glu mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.37 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Leu mutant

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Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.6 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Met mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.94 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Asp mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.95 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Thr439Val mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

2.0 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Ser mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.26 μmol/l

Effect (Pharmacological Data)

cardiac output; effect on

Species or Test-System (Pharmacological Data)

heart of Wistar rat

Sex

male

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; aortic flow (AF) measured after perfusion

Further Details (Pharmacological Data)

further invest. in presence of tyrosine kinase inhibitor genistein (37 μM); control: standard buffer

Results

title comp. alone had no effect but reduced AF in presence of genistein; table

Frascarelli, Sabina; Ghelardoni, Sandra; Chiellini, Grazia; Vargiu, Romina; Ronca-Testoni, Simonetta; Scanlan, Thomas S.; Grandy, David K.; Zucchi, Riccardo; European Journal of Pharmacology; vol. 587; nb. 1-3; (2008); p. 231 - 236, View in Reaxys 93 of 193

Effect (Pharmacological Data)

coronary flow; decrease of

Species or Test-System (Pharmacological Data)

heart of Wistar rat

Sex

male

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; coronary flow measured after perfusion

Further Details (Pharmacological Data)

further invest. in presence of tyrosine kinase inhibitor genistein; control: standard buffer

Comment (Pharmacological Data)

No effect

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94 of 193

Effect (Pharmacological Data)

inotropic neg.

Species or Test-System (Pharmacological Data)

heart of Wistar rat

Sex

male

Concentration (Pharmacological Data)

Ca. 1E-06 - 0.0003 mol/l

Method (Pharmacological Data)

isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; cardiac output (CO) at all doses tested and peak systolic aortic pressure (PAP) measured after perfusion

Further Details (Pharmacological Data)

further invest. of 100 μM title comp. for time course during perfusion, and in presence of tyrosine kinase inhibitor genistein; control: standard buffer; reference comp.: thyronamine, 3-iodothyronamine

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 242 μmol/l

Results

title comp. dose-dependently reduced CO at conc. >1E-4 M, with maximum by ca. 38percent at highest dose; further reduction of CO in presence of genistein; title comp. also decreased PAP; table, figures

Effect (Pharmacological Data)

chronotropic pos.

Species or Test-System (Pharmacological Data)

heart of Wistar rat

Sex

male

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; heart rate (HR) monitored during perfusion

Further Details (Pharmacological Data)

further invest. in presence tyrosine kinase inhibitor genistein or β-adrenergic blocker propranolol; control: standard buffer; reference comp.: thyronamine, 3-iodothyronamine

Results

title comp. increased HR by ca. 20-35percent vs. baseline; effect was blunted in presence of genistein and abolished by propranolol; table, figure

Effect (Pharmacological Data)

DNA; examination of

Species or Test-System (Pharmacological Data)

leukemic U937 cells of human

Concentration (Pharmacological Data)

0.5 - 5 mmol/l

Method (Pharmacological Data)

cells treated with various conc. of title comp. for 24 h; DNA extracted and separated by agarose gel electrophoresis; gel stained with ethidium bromide and imaged with FluorImager

Results

title comp. induced DNA fragmentation at conc. >= 3 mM; fig.

Inagaki, Shyuichiro; Morimura, Shigeru; Gondo, Kazunobu; Tang, Yueqin; Akutagawa, Hiroshi; Kida, Kenji; Bioscience, Biotechnology and Biochemistry; vol. 71; nb. 2; (2007); p. 371 - 379, View in Reaxys 97 of 193

Effect (Pharmacological Data)

drug interaction

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Species or Test-System (Pharmacological Data)

Caco-2 cells

Concentration (Pharmacological Data)

<= 30 mmol/l

Method (Pharmacological Data)

uptake of <3H>clonidine (3 nmol/l) by cell monolayer measured at pH 7.5 for 2 min or pH 8.5 in the absence or presence of title comp.; liquid scintillation counting

Further Details (Pharmacological Data)

inhibition of <3H>clonidine transport by title comp. investigated; control: <3H>clonidine uptake without title comp. = 100 percent

Results

<3H>clonidine uptake at pH 7.5 in the presence of 2 mmol/l title comp. was 68 percent (table); Ki = 2.5 mmol/l and 1.0 mmol/l for pH 7.5 and 8.5, respectively (table, diagram)

Fischer, Wiebke; Metzner, Linda; Hoffmann, Kathrin; Neubert, Reinhard H. H.; Brandsch, Matthias; Pharmaceutical Research; vol. 23; nb. 1; (2006); p. 131 - 137, View in Reaxys 98 of 193

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

colon cancer CaCo2 cells

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO or H2O and further diluted with fresh complete medium

Method (Pharmacological Data)

standard tetrazolium MTT assay; test cells incubated with title comp.; MTT reagent added; after 4 h incubation at 37 deg C medium removed, DMSO added; formed MTT product dissolved in DMSO; absorbance at 560 nm recorded

Further Details (Pharmacological Data)

before addition of title comp. exponentially growing cells plated into 96-well plates and incubated for 72 h at 37 deg C

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

198.0 μmol/l

Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji; Nahar, Lutfun; Kong-Thoo-Lin, Paul; Sarker, Satyajit D.; Tetrahedron; vol. 62; nb. 48; (2006); p. 11172 - 11177, View in Reaxys 99 of 193

Effect (Pharmacological Data)

membrane currents; inhibition of

Species or Test-System (Pharmacological Data)

Xenopus laevis oocyte

Method (Pharmacological Data)

oocytes expressing rat NMDA receptor subunits NR1a+2B; Ca(2+)- and Mg(2+)-free solution at 18 deg C; two-electrode voltage clamp at -70 mV; bath application of title comp.; inhibition of currents induced by 100 μmol/l glutamate and 10 μmol/l glycine

Further Details (Pharmacological Data)

NMDA: N-methyl-D-aspartate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

138 μmol/l

Kloda, Anna; Adams, David J.; British Journal of Pharmacology; vol. 144; nb. 3; (2005); p. 323 - 330, View in Reaxys 100 of 193 Effect (Pharmacological Data)

membrane currents; inhibition of

Species or Test-System (Pharmacological Data)

Xenopus laevis oocyte

Method (Pharmacological Data)

oocytes expressing rat NMDA receptor subunits NR1a+2B; Ca(2+)- and Mg(2+)-free solution at 18 deg C; two-electrode voltage clamp at -120 mV; bath application of title comp.; inhibition of currents induced by 100 μmol/l glutamate and 10 μmol/l glycine

Further Details (Pharmacological Data)

NMDA: N-methyl-D-aspartate

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

32 μmol/l

Kloda, Anna; Adams, David J.; British Journal of Pharmacology; vol. 144; nb. 3; (2005); p. 323 - 330, View in Reaxys 101 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Wistar rat kidney P2 membranes

Sex

male

Method (Pharmacological Data)

affinity at α2-adrenergic receptor evaluated by radioligand (<3H>RX821002) competition binding assay

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

19000 nmol/l

receptor; binding activity

Species or Test-System (Pharmacological Data)

Wistar rat whole brain P2 membranes

Sex

male

Method (Pharmacological Data)

affinity at imidazoline I2 receptor evaluated by radioligand (<3H>2-BFI) competition binding assay

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

5400 nmol/l

transport; inhibition of

Species or Test-System (Pharmacological Data)

human choriocarcinoma JEG-3 cell monolayers

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

uptake of <3H>clonidine (3 nmol/l, pH 7.5, 1 min, room temperature) measured in presence of title comp.; cells solubilized and prepared for scintillation counting

Further Details (Pharmacological Data)

control: <3H>clonidine uptake in absence of title comp.: 100 percent

Results

<3H>clonidine uptake decreased to 87 percent in presence of title comp.

Mueller, Johanna; Neubert, Reinhard; Brandsch, Matthias; Pharmaceutical Research; vol. 21; nb. 4; (2004); p. 692 - 694, View in Reaxys 104 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

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Method (Pharmacological Data)

competition binding assay; 0.1 nmol/l <125I>-DOI used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 5 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharmacological Data)

nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); DOI: 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane; title comp. binding affinity to recombinant 5-HT2A receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

6.66 dimensionless

Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 370; nb. 2; (2004); p. 114 - 123, View in Reaxys 105 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

CHO-K1 cell membranes expressing human 5-HT2B receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 5 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 4 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharmacological Data)

nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding affinity to recombinant 5-HT2B receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

6.99 dimensionless

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2C receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 1 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharmacological Data)

nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding affinity to recombinant 5-HT2C receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

5.63 dimensionless

agonist

Endpoint of Effect (Pharmacological Data)

arachidonic acid (AA) release

Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

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Concentration (Pharmacological Data)

0.0001 - 10 μmol/l

Method (Pharmacological Data)

cells labeled with <3H>AA for 4 h; washed three times with DMEM and incubated with title comp. for 30 min at 37 deg C; <3H>AA in medium counted

Further Details (Pharmacological Data)

5-HT = 5-hydroxytryptamine; DMEM = Dulbecco's modified Eagle's medium; control: without title comp.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1200 nmol/l

Results

title comp. stimulated the <3H>AA accumulation conc.-dependently (table)

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys 108 of 193 Effect (Pharmacological Data)

agonist

Endpoint of Effect (Pharmacological Data)

IPs accumulation

Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

0.001 - 10 μmol/l

Method (Pharmacological Data)

cells loaded with myo-<2-3H(N)>inositol and pretreated with 10 μmol/l pargyline and 10 mmol/l LiCl for 15 min at 37 deg C in CMRL-1066 media; then title comp. added for 30 min; <3H>IPs of cell lysate separated by ion-exchange chromatography and counted

Further Details (Pharmacological Data)

5-HT = 5-hydroxytryptamine; IPs = a mixture of inositol mono- bis-, and triphosphate; control: without title comp.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1100 nmol/l

Results

title comp. stimulated the <3H>IPs accumulation conc.-dependently (table)

receptor; binding activity

Endpoint of Effect (Pharmacological Data)

<125I>2,5-dimethoxy-4-iodoamphetamine (DOI) binding

Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

1E-05 - 10 μmol/l

Method (Pharmacological Data)

competition binding study; cells incubated with 2E-1 nmol/l <125I>DOI in the presence title comp. for 60 min at 25 deg C in Tris-EDTA buffer, pH 7.4; nonspecific binding determ. with 10 μmol/l cinanserin; filter-bound radioactivity counted

Further Details (Pharmacological Data)

5-HT = 5-hydroxytryptamine; control: without title comp.

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

49 nmol/l

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys

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110 of 193

Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

calf thymus DNA

Concentration (Pharmacological Data)

1 - 10 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

DNA exposed to title comp. with/without S9 (conc. 1.5 percent); incubated at 37 deg C for 3 h; during the last 1 h and after purified RNAses added; analyzed for DNA adducts by 32P-postlabeling analysis

Further Details (Pharmacological Data)

S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; RNAses: ribonucleases; solvent (K2HPO4, pH 7.0, containing isocitrate and NADP(+)) as control

Results

title comp. no significantly produced DNA adducts in the presence of S9 (table)

Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 111 of 193

Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

Escherichia coli WP2 uvrA pKM101

Concentration (Pharmacological Data)

4000 - 12000 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

log-phase culture added to molten agar (5E7 cells/ml) and buffer/co-factor mix with/without S9 and with title comp.; then placed on solid agar; incub. at 37 deg C for 48 h; colonies number counted and analyzed DNA adducts by 32P-postlabeling analysis

Further Details (Pharmacological Data)

S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; solid agar with/without histidine or tryptophan; benzo(a)pyrene and 2-aminoanthracene as positive control (induced mutations)

Results

title comp. showed induced mutations and DNA adducts in a dose-dependent manner (diagrams)

Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA1535

Concentration (Pharmacological Data)

4000 - 12000 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Comment (Pharmacological Data)

No effect

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Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA100

Concentration (Pharmacological Data)

4000 - 12000 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Results

title comp. showed induced mutations and DNA adducts in a dose-dependent manner (diagrams)

Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA98

Concentration (Pharmacological Data)

4000 - 12000 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

mutagenic

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA97a

Concentration (Pharmacological Data)

4000 - 12000 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

Further Details (Pharmacological Data)

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Results

title comp. showed induced mutations and DNA adducts in a dose-dependent manner (diagrams)

Effect (Pharmacological Data)

genotoxic

Species or Test-System (Pharmacological Data)

rat hepatocytes

Concentration (Pharmacological Data)

1 - 10 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

cells from induced (PB/β-NF) or uninduced rats treated for 3 h at 37 deg C; alkaline elution assay; DNA single-strand breaks and adduct formation determined by 32P-postlabeling analysis

Further Details (Pharmacological Data)

PB/β-NF: phenobarbital/β-naphthoflavone; aflatoxin B1 (AFB1), γ-radiation and benzo(a)pyrene as positive controls: γ-radiation produced DNA strand breaks, AFB1 produced strand breaks in uninduced hypatocytes; two replicates

Results

title comp. showed negative effect for the induction of DNA single-strand breaks in cultured primary hepatocytes isolated from uninduced or induced rats with PB/β-NF; intensity of DNA adduct formation in a dose-dependent manner (table)

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

CHO cells

Concentration (Pharmacological Data)

1 - 4 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

culture (2-3E6 cells) incubated with title comp. for 3 h; at the end for the last 30 min of incubation added BrdUrd for staining; reduction in total cell DNA (PI) number analyzed using flow cytometer

Further Details (Pharmacological Data)

BrdUrd: 5-bromodeoxyuridine; PI: propidium iodide

Results

title comp. increased in a dose-dependent manner both with/without S9 (diagrams)

Effect (Pharmacological Data)

DNA synthesis; inhibition of

Species or Test-System (Pharmacological Data)

CHO cells

Concentration (Pharmacological Data)

1 - 4 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

culture (2-3E6 cells) incubated with title comp. for 3 h; at the end for the last 30 min of incubation added BrdUrd and FITC labeled secondary antibody to mouse anti-BrdUrd; inhibition of DNA synthesis measured as suppression of BrdUrd uptake/S phase

Further Details (Pharmacological Data)

BrdUrd: 5-bromodeoxyuridine; two replicates

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Results

title comp. induced strong (dose-dependent) inhibition of DNA synthesis with/without S9 (diagrams)

Effect (Pharmacological Data)

genotoxic

Species or Test-System (Pharmacological Data)

CHO cells

Concentration (Pharmacological Data)

1 - 4 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

culture (2-3E6 cells) incubated with title comp. for 3 h; at the end for the last 30 min of incubation added BrdUrd and FITC labeled secondary antibody to mouse anti-BrdUrd; DNA adducts measured

Further Details (Pharmacological Data)

BrdUrd: 5-bromodeoxyuridine; two replicates

Comment (Pharmacological Data)

No effect

genotoxic

Species or Test-System (Pharmacological Data)

CHO cells

Concentration (Pharmacological Data)

1 - 4 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

culture (2-3E6 cells) incubated with title comp. with/without S9 for 3 h; then once more incubated for an additional 17 h title comp.; percent of cells (in methaphase) with chromosomal aberration (Abs) in treated culture evaluated

Further Details (Pharmacological Data)

S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; cyclophosphamide and mitomycin C as positive controls (induced Abs as expected)

Results

title comp. produced no significant increases in Abs over the controls with/without S9 (diagrams)

cytotoxicity

Species or Test-System (Pharmacological Data)

rat hepotocytes

Concentration (Pharmacological Data)

1 - 10 mmol/l

Kind of Dosing (Pharmacological Data)

title comp. stock solution prepared in DMSO

Method (Pharmacological Data)

cells from induced (PB/β-NF) or uninduced rats treated for 3 h at 37 deg C; Trypan blue dye exclusion viability assay; cell viability after treated or 3 h and intracellular ATP determined

Further Details (Pharmacological Data)

PB/β-NF: phenobarbital/β-naphthoflavone; aflatoxin B1, γ-radiation and benzo(a)pyrene as positive controls

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Results

title comp. showed decreased number of cell viability and cellular ATP content of controls in a dose-dependent manner (table)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

cathepsin K

Concentration (Pharmacological Data)

100 mg/l

Kind of Dosing (Pharmacological Data)

in DMSO

Method (Pharmacological Data)

in the presence of 160 ng/mL cathepsin K and 20 μmol/l ZFR-AMC (phenylalanine-arginine-aminomethylcoumarin)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

15 μmol/l

Patil, Ashok D.; Freyer, Alan J.; Carte, Brad; Taylor, Paul B.; Johnson, Randall K.; Faulkner, D. John; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 628 - 629, View in Reaxys 123 of 193 Effect (Pharmacological Data)

enzyme; examination of

Species or Test-System (Pharmacological Data)

coclaurine N-methyltransferase

Method (Pharmacological Data)

0.1 mM norreticuline, 100 mM potassium phosphate buffer, 1 mM (methyl-3H)-S-adenosyl-L-methionine, 20 μl of enzyme soln., 30 deg C, 60 min; 1 mM (S)-coclaurine

Results

relative activity (vs (S)-coclaurine when activity = 100) is 0 (no methylation)

Choi, Kum-Boo; Morishige, Takashi; Sato, Fumihiko; Phytochemistry; vol. 56; nb. 7; (2001); p. 649 - 655, View in Reaxys 124 of 193 Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

rat brain stem

Kind of Dosing (Pharmacological Data)

decreasing concentrations: 5.0; 2.5; 1.0; 0.5; 0.25; 0.1; 0.05; 0.01; 0.005 mg/L

Method (Pharmacological Data)

as in Knoll, J. et al. Life Sci. 1996, 58, 2101; LT incorp. into transmitter stores of brain stem slices by preincubation; counting of released LT amount before and after brain stem stimulation with/without title comp.; each concn. for two brain stems

Further Details (Pharmacological Data)

LT: labeled transmitter (5-hydroxy-<G-3H>-tryptamine creatinine sulphate (10-20 Ci/ mmol)); stimulation by rectang. pulses 3 Hz, 1 ms, 60 V, 3 min; start with 3 3-min resting periods before first stimulation, then 7 resting periods between stimulations

Results

title comp. concn. which increases on both stems at least 25 percent of <3H>-serotonin amount released after stimulation is 0.25 mg/L compared with 5.0 mg/L for fluoxetine and > 5 mg/L for bromocryptine, pergolide, clorgyline, lazabemide and amantadine

Yoneda, Fumio; Moto, Toshiaki; Sakae, Masatoshi; Ohde, Hironori; Knoll, Berta; Miklya, Ildiko; Knoll, Joseph; Bioorganic and Medicinal Chemistry; vol. 9; nb. 5; (2001); p. 1197 - 1212, View in Reaxys 125 of 193 Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

rat brain stem

Kind of Dosing (Pharmacological Data)

decreasing concentrations: 5.0; 2.5; 1.0; 0.5; 0.25; 0.1; 0.05; 0.01; 0.005 mg/L

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Method (Pharmacological Data)

Further Details (Pharmacological Data)

LT: labeled transmitter (<2,5,6-3H>-dopamine (5-15 Ci/mmol)); stimulation by rectangular pulses 3 Hz, 1 ms, 60 V, 3 min; start with 3 consecutive 3-min resting periods before first stimulation, then 7 resting periods between stimulations

Results

title comp. concn. which increases on both stems at least 25 percent of LT amount released after stimulation is 2.5 mg/L compared with 0.25 mg/L for bromocryptine, 0.5 mg/L for pergolide and > 5 mg/L for fluoxetine, clorgyline, lazabemide and amantadine

transmitter releasing

Species or Test-System (Pharmacological Data)

rat brain stem

Kind of Dosing (Pharmacological Data)

decreasing concentrations: 5.0; 2.5; 1.0; 0.5; 0.25; 0.1; 0.05; 0.01; 0.005 mg/L

Method (Pharmacological Data)

Further Details (Pharmacological Data)

LT: labeled transmitter (1-<7,8-3H>-noradrenaline (30-50 Ci/mmol)); stimulation by rectangular pulses 3 Hz, 1 ms, 60 V, 3 min; start with 3 consecutive 3-min resting periods before first stimulation, then 7 resting periods between stimulations

Results

title comp. concn. which increases on both stems at least 25 percent of LT amount released after stimulation is 2.5 mg/L compared with 2.5 mg/L for bromocryptine and > 5 mg/L for pergolide, fluoxetine, clorgyline, lazabemide and amantadine

tumor cell migration; inhibition of

Species or Test-System (Pharmacological Data)

murine colon 26-L5 adenocarcinoma cell line

Concentration (Pharmacological Data)

100 mg/l

Kind of Dosing (Pharmacological Data)

title comp. added in dimethyl sulfoxide

Method (Pharmacological Data)

2E5 cells incub. with var. conc. of title comp. in RPMI-1640 medium with 0.1 percent bovine serum albumin for 30 min on ice, then added to upper compartment of Transwell chamber, incub. 3 h at 37 deg C; cells stained, migrated cells extracted, absorbance det.

Further Details (Pharmacological Data)

vehicle control; cells stained with 0.5 percent crystal violet for 30 min

Results

title comp. inhibited tumor cell migration (30 - 40 percent inhibition of control)

Ogasawara, Masaru; Matsubara, Toshiyuki; Suzuki, Hideyo; Biological and Pharmaceutical Bulletin; vol. 24; nb. 6; (2001); p. 720 - 723, View in Reaxys 128 of 193 Effect (Pharmacological Data) Species or Test-System (Pharmacological Data)

enzyme; inhib. of phenylalanine ammonia-lyase

Kim, Seong Hwan; Kronstad, James W.; Ellis, Brian E.; Phytochemistry; vol. 58; nb. 6; (2001); p. 849 - 857, View in Reaxys 129 of 193 Effect (Pharmacological Data) Species or Test-System (Pharmacological Data)

agonist HEK293 cells expressing rTAR1

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Concentration (Pharmacological Data)

Ca. 1E-09 - 1E-05 mol/l

Method (Pharmacological Data)

cells incubated in KRH with 100 μmol/l 3-isobutyl-1-methylxanthine and title comp. for 1 h at 37 deg C; cAMP content measured using competitive binding of <3H>cAMP to a cAMPbinding protein

Further Details (Pharmacological Data)

HEK: human embryonic kidney; rTAR1: rat trace amine receptor 1; reference comp.: forskolin; KRH: Krebs-Ringer-HEPES buffer

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

310 nmol/l

Results

title comp. induced cAMP production acting as agonist (diagram)

Bunzow; Sonders; Arttamangkul; Harrison; Zhang; Quigley; Darland; Suchland; Pasumamula; Kennedy; Olson; Magenis; Amara; Grandy; Molecular Pharmacology; vol. 60; nb. 6; (2001); p. 1181 - 1188, View in Reaxys 130 of 193 Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Phoma lingam virulent isolate BJ 125

Concentration (Pharmacological Data)

0.0002 mol/l

Method (Pharmacological Data)

in vitro; inoculated with fungal spores (2E9 per flask); minimal medium; incubation 14 days; metabolites isolated by preparative TLC

Metabolite XRN (Pharmacological Data)

170780; 143358

Metabolite (Pharmacological Data)

N-Acetyltryptamine; indole-3-acetic acid

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 131 of 193 Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Phoma lingam avirulent isolate Unity

Concentration (Pharmacological Data)

0.0002 mol/l

Method (Pharmacological Data)

in vitro; inoculated with fungal spores (2E9 per flask); minimal medium; incubation 5 days; metabolites isolated by preparative TLC

Metabolite XRN (Pharmacological Data)

125553; 129435

Metabolite (Pharmacological Data)

2-(3-indole)-ethanol; 1H-indole-3-carboxylic acid

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 132 of 193 Effect (Pharmacological Data)

fungistatic

Species or Test-System (Pharmacological Data)

Phoma lingam virulent isolate

Concentration (Pharmacological Data)

0.0001 - 0.0005 mol/l

Method (Pharmacological Data)

in vitro; mycelial radial growth bioassay; incubation time 72 h

Results

percent inhibition/dose (M): 0/1E-4, and 1/5E-4

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys

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133 of 193 Effect (Pharmacological Data)

fungistatic

Species or Test-System (Pharmacological Data)

Phoma lingam avirulent isolate Unity

Concentration (Pharmacological Data)

0.0001 - 0.0005 mol/l

Method (Pharmacological Data)

in vitro; mycelial radial growth bioassay; incubation time 72 h

Results

percent inhibition/dose (M): 0/1E-4, and 1/5E-4

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 134 of 193 Effect (Pharmacological Data)

fungistatic

Species or Test-System (Pharmacological Data)

Alternaria brassica

Concentration (Pharmacological Data)

0.0001 - 0.0005 mol/l

Method (Pharmacological Data)

in vitro; mycelial radial growth bioassay; incubation time 72 h

Comment (Pharmacological Data)

No effect

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 135 of 193 Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

deacetylipecoside synthase

Concentration (Pharmacological Data)

0.1 - 1.0 mM

Comment (Pharmacological Data)

No effect

De-Eknamkul, Wanchai; Suttipanta, Nitima; Kutchan, Toni M; Phytochemistry; vol. 55; nb. 2; (2000); p. 177 181, View in Reaxys 136 of 193 Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human liver microsomes

Concentration (Pharmacological Data)

0.1 - 500 μmol/l

Method (Pharmacological Data)

human liver samples were obtained from unrelated white Spanish patients (no liver disease); microsomal fractions were prepared; CYP3A enzyme activity was measured using the enzyme-specific substrate midazolam (0.5-20 μmol/l), incubated with title comp.

Further Details (Pharmacological Data)

midazolam and its main metabolites, 1'-hydroxymidazolam and 4-hydroxymidazolam analysed by HPLC

Comment (Pharmacological Data)

No effect

Martinez; Gervasini; Agundez; Carrillo; Ramos; Garcia-Gamito; Gallardo; Benitez; European Journal of Clinical Pharmacology; vol. 56; nb. 2; (2000); p. 145 - 151, View in Reaxys 137 of 193 Comment (Pharmacological Data)

weak inhibitory activity on NADPH-dependent lipid peroxidation in rat liver microsomes (IC50 260 μM)

Takahashi, Satoshi; Matsunaga, Takayuki; Hasegawa, Chika; Saito, Haruo; Fujita, Daisuke; Kiuchi, Fumiyuki; Tsuda, Yoshisuke; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 10; (1998); p. 1527 - 1529, View in Reaxys

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138 of 193 Effect (Pharmacological Data)

inhibition of forskolin-induced cAMP production

Species or Test-System (Pharmacological Data)

HA7 cell line

Exposure Period (Pharmacological Data)

10 min

Method (Pharmacological Data)

cell preincubation; forskolin (100 μM) and title compd. addn., incubation (10 min, room temp.), cellular extract anal.

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

5.36 -log(M)

Koek; Patoiseau; Assie; Cosi; Kleven; Dupont-Passelaigue; Carilla-Durand; Palmier; Valentin; John; Pauwels; Tarayre; Colpaert; Journal of Pharmacology and Experimental Therapeutics; vol. 287; nb. 1; (1998); p. 266 283, View in Reaxys 139 of 193 Effect (Pharmacological Data)

intracellular cAMP stimulation

Species or Test-System (Pharmacological Data)

murine fibroblasts (LMtk-) cell line

Exposure Period (Pharmacological Data)

10 min

Method (Pharmacological Data)

cell line membrane preincubated (HEPES-buffered saline, pH 7.4, 37 deg C, 30 min), then incubated in presence of title compd.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

13342 nmol/l

Results

affinity const. Ki = 57 nM

Adham, Nika; Zgombick, John M.; Bard, Jonathan; Journal of Pharmacology and Experimental Therapeutics; vol. 287; nb. 2; (1998); p. 508 - 514, View in Reaxys 140 of 193 Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

20 μmol/l

Method (Pharmacological Data)

ability of title comp. to activate PLC-mediated IP accumulation studied; cells labeled with 1 μCi/ml myo-<3H>inositol (24 h, 37 deg C) incubated with title comp. for 10 min; mono-, di-, triphosphates of inositol separated by ion exchange chromatography

Further Details (Pharmacological Data)

radioactivity counted by liquid scintillation; cells expressing human 5-HT2A receptors; 5HT: 5-hydroxytryptamine; PLC: phospholipase C; IP: inositol phosphates; 5-HT used as reference comp.; Emax: maximal response

Results

Emax title comp./Emax 5-HT ca. 0.60 (figure)

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 141 of 193 Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

20 μmol/l

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Method (Pharmacological Data)

ability of title comp. to activate PLA2-mediated arachidonic acid release studied; cells labeled with 0.1 μCi/ml <14C>arachidonic acid (4 h, 37 deg C) incubated with title comp. for 10 min; radioactivity measured by liquid scintillation counting

Further Details (Pharmacological Data)

cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; PLA2: phospholipase A2; 5-HT used as reference comp.; Emax: maximal response

Results

Emax title comp./Emax 5-HT ca.1.4 (figure)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

20 μmol/l

Method (Pharmacological Data)

ability of title comp. to increase Ca(2+) conc. studied; cells loaded with Fura-2; intracellular Ca(2+) conc. determined by measuring fluorescence (340/380 nm)

Further Details (Pharmacological Data)

cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; 5-HT used as reference comp.; Emax: maximal response

Results

Emax title comp./Emax 5-HT ca. 0.45 (figure)

inhibition of 2-<125I>-iodomelatonin binding in membrane preparations of rat testes, IC50=31000 nmol/L

Vera; Tijmes; Valladares; Steroids; vol. 62; nb. 2; (1997); p. 226 - 229, View in Reaxys 144 of 193 Comment (Pharmacological Data)

substrate specificity for phenylethylamine oxidase of Arthrobacter globiformis IFO 12137 (ATCC 8010), Km = 0.017 mM, Vmax = 7.63 μmol/min/mg, Vmax/Km = 449; relative reaction rate 16percent of that observed with 2-phenylethylamine at 1.0 mM

Shimizu, Eiichi; Ohta, Keiichi; Takayama, Shigeo; Kitagaki, Yuzuru; Tanizawa, Katsuyuki; Yorifuji, Takamitsu; Bioscience, Biotechnology and Biochemistry; vol. 61; nb. 3; (1997); p. 501 - 505, View in Reaxys 145 of 193 Effect (Pharmacological Data)

transport

Species or Test-System (Pharmacological Data)

Caco-2 cells

Concentration (Pharmacological Data)

50 μmol/l

Exposure Period (Pharmacological Data)

5 - 60 min

Method (Pharmacological Data)

cells seeded on microporous membrane filters inside Transwell cell culture chambers; incubation medium; pH 7.5 (apical side); 37 deg C or ambient temp.; also in the presence of imipramine; samples from basal side withdrawn; HPLC

Results

imipramine reduced drug uptake at pH 7.5

Iseki, Ken; Kaido, Koh-Ichi; Kobayashi, Michiya; Sugawara, Mitsuru; Miyazaki, Katsumi; Biological and Pharmaceutical Bulletin; vol. 20; nb. 7; (1997); p. 794 - 799, View in Reaxys 146 of 193 Effect (Pharmacological Data)

transport

Species or Test-System (Pharmacological Data)

rat intestinal brush-border membrane vesicles

Concentration (Pharmacological Data)

1 mmol/l

Exposure Period (Pharmacological Data)

0.5 - 30 min

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Method (Pharmacological Data)

vesicles from small intestine of rats (Wistar, male, 175-240 g); pH 7.5; rapid filtration technique; drug trapped on filter measured by HPLC; also in the presence of imipramine

Results

imipramine reduced drug uptake at pH 7.5

muscle contractive

Species or Test-System (Pharmacological Data)

Beagle dog colon longitudinal muscle

Sex

male and female

Concentration (Pharmacological Data)

Ca. 1E-06 - 0.0001 mol/l

Method (Pharmacological Data)

dogs (7-14kg) decerebrated, a piece of midcolon ca. 5 cm dissected, luminal contents removed; mucosa, submucosa and mesenterium dissected, strips of longitudinal muscle prepared

Further Details (Pharmacological Data)

concentration-response curve in the presence of 10 nM SB 204070

Results

concentration-dependent contraction: title compound concentration (logM), ca. contraction percent: -6, 0; -5, 15

Prins, Nicolaas H.; Briejer, Michel R.; Schuurkes, Jan A.J.; British Journal of Pharmacology; vol. 120; nb. 4; (1997); p. 714 - 720, View in Reaxys 148 of 193 Effect (Pharmacological Data)

protein binding

Species or Test-System (Pharmacological Data)

Wistar rat brain cortical membranes

Sex

male

Method (Pharmacological Data)

membranes (0.5-0.6 mg protein/ml) were incubated with 1.3-1.5 nmol/l <3H>citalopram for 60 min at 22 deg C in presence of title comp.; inhibition of <3H>citalopram binding to 5-HT transporter was assayed by liquid scintillation spectrometry

Further Details (Pharmacological Data)

incubation buffer (mmol/l): 50 Tris-HCl, 120 NaCl, 5 KCl, pH 7.4; Ki=IC50/(1+C/Kd); Hill coefficient (nH) was determined from Hill plots of saturation experiments; 5-HT: 5-hydroxytryptamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3600 nmol/l

Results

nH = 0.87 (table)

Paehkla, Rein; Raego, Lembit; Callaway, James J.; Airaksinen, Mauno M.; Pharmacology and Toxicology; vol. 80; nb. 3; (1997); p. 122 - 126, View in Reaxys 149 of 193 Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

HL-60 cell membranes

Concentration (Pharmacological Data)

1 - 3000 μmol/l

Method (Pharmacological Data)

effect of title compound on GTPase activity studied; dibutyryl-cAMP differentiated HL-60 cells; purified by repeated centrifugation and resuspension; disintegrated by 25 bar N2 cavitation at 4 deg C; EDTA and mercaptoethanol added; centrifuged

Further Details (Pharmacological Data)

incubation in pH 7.4 medium containing membranes, adenosine 5'-(βγ-imido)triphosphate, (γ-32P)GTP, and bovine serum albumin at 25 deg C, for 15-25 min

Comment (Pharmacological Data)

No effect

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Klinker, Jan F.; Seifert, Roland; Damm, Henning; Rommelspacher, Hans; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1621 - 1626, View in Reaxys 150 of 193 Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

bovine retinal G-protein transducin

Concentration (Pharmacological Data)

1 - 3000 μmol/l

Method (Pharmacological Data)

effect of title compound on GTPase activity studied; transducin prepared from bovine rod outer segment disk membranes

Further Details (Pharmacological Data)

incubation in pH 7.4 medium containing transducin, ATP, adenosine 5'-(βγ-imido)triphosphate, (γ-32P)GTP and bovine serum albumin at 25 deg C, 15-25 min

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

350 μmol/l

Results

effect in 1 mmol/l concentration of title compound: 13 percent above basal

Klinker, Jan F.; Seifert, Roland; Damm, Henning; Rommelspacher, Hans; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1621 - 1626, View in Reaxys 151 of 193 Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

recombinant human IDO

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

recombinant human indoleamine 2,3-dioxygenase (IDO) from E. coli YA21; activity assayed by measuring the kynurenine; yellow-coloured complex measured by spectrophotometer

Further Details (Pharmacological Data)

activity of IDO in the presence of 1 mM of title comp.; relative to the activity with 200 μM Ltryptophan

Results

percentage of in vitro activity 32 percent and inhibition 28 percent

agonist

Species or Test-System (Pharmacological Data)

neuroblastoma cells of N1E-115 mouse

Method (Pharmacological Data)

5-HT3 receptor-mediated ion currents evoked by title comp. in cells investigated in wholecell voltage clamp experiments at 20-24 deg C

Further Details (Pharmacological Data)

potency for desensitization (IC50); Student's t test

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

17 μmol/l

Results

desensitizes completely 5-HT3 receptor-mediated inward current; conc.-effect curve; recovery from desensitization is single exponential

Van Hooft, Johannes A.; Vijverberg, Henk P.M.; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 839 846, View in Reaxys 153 of 193 Effect (Pharmacological Data)

agonist

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Species or Test-System (Pharmacological Data)

neuroblastoma cells of N1E-115 mouse

Method (Pharmacological Data)

5-HT3 receptor-mediated ion currents evoked by title comp. in cells investigated in wholecell voltage clamp experiments at 20-24 deg C

Further Details (Pharmacological Data)

potency for activation (EC50); Student's t test

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

44 μmol/l

Results

partial agonism on 5-HT3 receptors; Emax=33.0 percent; time constant of inward current decay 22.7 s (n=6) for 100 μM of title comp.

Van Hooft, Johannes A.; Vijverberg, Henk P.M.; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 839 846, View in Reaxys 154 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mutant A5.46S 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

174 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 155 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

wild-type 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

284 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 156 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mutant S5.46A 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

3493 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 157 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

wild-type 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

929 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 158 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

h5-HT1Dβ L929sA cells

Method (Pharmacological Data)

radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-alniditan (2 nM)

Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

150 nmol/l

Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 159 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

h5-HT1Dβ L929sA cells

Method (Pharmacological Data)

radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-HT (4 nM)

Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

58 nmol/l

receptor; binding activity

Species or Test-System (Pharmacological Data)

h5-HT1Dα C6 glioma cells

Method (Pharmacological Data)

radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-HT (4 nM)

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Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

42 nmol/l

receptor; binding activity

Species or Test-System (Pharmacological Data)

h5-HT1Dα C6 glioma cells

Method (Pharmacological Data)

radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>alniditan (2 nM)

Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

141 nmol/l

receptor; binding activity

Species or Test-System (Pharmacological Data)

5-HT1D calf substantia nigra

Method (Pharmacological Data)

radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>alniditan (2 nM)

Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

91 nmol/l

receptor; binding activity

Species or Test-System (Pharmacological Data)

5-HT1D calf substantia nigra

Method (Pharmacological Data)

radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-HT (4 nM)

Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

34 nmol/l

inhibition of binding to receptor

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Species or Test-System (Pharmacological Data)

human 5-HT1B receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1B plasmid; cellular membranes prepared; radioligand binding with 0.5 nM <3H>-5-carboxamidotryptamine in presence of title comp., 25 deg C, 30 min

Further Details (Pharmacological Data)

5-HT=serotonin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6.42 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 165 of 193 Effect (Pharmacological Data)

inhibition of nucleotide formation

Species or Test-System (Pharmacological Data)

human 5-HT1B receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1B plasmid; incub. with 100 μM forskolin plus title comp., 37 deg C, 5 min; cellular cAMP content by radioimunoassay

Further Details (Pharmacological Data)

EC50: conc. of title comp. yielding 50 percent of the inhibition by 1 μM serotonin (5-HT)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

100.00 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 166 of 193 Effect (Pharmacological Data)

inhibition of nucleotide formation

Species or Test-System (Pharmacological Data)

human 5-HT1D receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pRcRSV/5-HT1D plasmid; incub. with 100 μM forskolin plus title comp., 37 deg C, 5 min; cellular cAMP content by radioimunoassay

Further Details (Pharmacological Data)

EC50: conc. of title comp. yielding 50 percent of the inhibition by 1 μM serotonin (5-HT)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

24.70 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 167 of 193 Effect (Pharmacological Data)

inhibition of nucleotide formation

Species or Test-System (Pharmacological Data)

human 5-HT1D receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1D plasmid; incub. with 100 μM forskolin plus title comp., 37 deg C, 5 min; cellular cAMP content by radioimunoassay

Further Details (Pharmacological Data)

EC50: conc. of title comp. yielding 50 percent of the inhibition by 1 μM serotonin (5-HT)

Type (Pharmacological Data)

EC50

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Value of Type (Pharmacological Data)

53.30 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 168 of 193 Effect (Pharmacological Data)

inhibition of binding to receptor

Species or Test-System (Pharmacological Data)

human 5-HT1D receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1D plasmid; cellular membranes prepared; radioligand binding with 3 nM <3H>-sumatriptan in presence of title comp., 25 deg C, 30 min

Further Details (Pharmacological Data)

5-HT=serotonin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

27.23 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 169 of 193 Effect (Pharmacological Data)

inhibition of binding to receptor

Species or Test-System (Pharmacological Data)

human 5-HT1D receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1D plasmid; cellular membranes prepared; radioligand binding with 0.5 nM <3H>-5-carboxamidotryptamine (5-CT) in presence of title comp., 25 deg C, 30 min

Further Details (Pharmacological Data)

5-HT=serotonin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

18.69 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 170 of 193 Effect (Pharmacological Data)

inhibition of binding to receptor

Species or Test-System (Pharmacological Data)

human 5-HT1D receptor

Method (Pharmacological Data)

C6-glial cells (CCL 107, rat), ATCC, stably transfected with pRcRSV/5-HT1D plasmid; cellular membranes prepared; radioligand binding with <3H>-5-carboxamidotryptamine in presence of title comp., 25 deg C, 30 min

Further Details (Pharmacological Data)

5-HT=serotonin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

14.59 nmol/l

Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 171 of 193 Comment (Pharmacological Data)

affinity and intrinsic efficacy at 5-HT1D receptor in rabbit saphenous vein and affinity at 5HT2A receptor in rabbit aorta

Glen, Robert C.; Martin, Graeme R.; Hill, Alan P.; Hyde, Richard M.; Woollard, Patrick M.; et al.; Journal of Medicinal Chemistry; vol. 38; nb. 18; (1995); p. 3566 - 3580, View in Reaxys

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172 of 193 Effect (Pharmacological Data)

muscle relaxant

Species or Test-System (Pharmacological Data)

Dunkin-Hartley guinea-pig ileum

Sex

male

Method (Pharmacological Data)

250-350 g pigs killed, ileal segments suspended in Krebs solution + (μM) cocaine 10, corticosterone 10, pargyline 5, indomethacin 1, atropine 1 at 37 deg C, pH 7.4; H: without/ with desensitization by 60 min equilibr. with 3 μM 5-carboxamidotryptamine

Further Details (Pharmacological Data)

contractions induced by 1 μM histamine (H) or 30 nM substance P (SP) for 30 s, 5 min dose-cycle; when stable contractions, title comp. added 3 min before spasmogen; change in isometric tension recorded

Comment (Pharmacological Data)

No effect

Carter; Champney; Hwang; Eglen; European Journal of Pharmacology; vol. 280; nb. 3; (1995); p. 243 - 250, View in Reaxys 173 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mouse 1C11 cells

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

in vitro; cells cultured for 2 d in the presence of 1 mM dibutyryl-cAMP and 0.05 percent cyclohexane carboxylic acid; 5HT2B receptors; competitive binding with <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane

Further Details (Pharmacological Data)

inhibition of <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane binding; diagram

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

6.83 dimensionless

Loric, Sylvain; Maroteaux, Luc; Kellermann, Odile; Launay, Jean-Marie; Molecular Pharmacology; vol. 47; nb. 3; (1995); p. 458 - 466, View in Reaxys 174 of 193 Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mouse LMTK- fibroplast cells

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

in vitro; cells stably transfected with NP75 cDNA; 5-HT2B receptors; competitive binding with <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane

Further Details (Pharmacological Data)

inhibition of <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane binding; diagram

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

6.87 dimensionless

Loric, Sylvain; Maroteaux, Luc; Kellermann, Odile; Launay, Jean-Marie; Molecular Pharmacology; vol. 47; nb. 3; (1995); p. 458 - 466, View in Reaxys 175 of 193 Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

human saliva

Sex

male

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Concentration (Pharmacological Data)

1 - 10 mg/l

Method (Pharmacological Data)

in vitro; TBC and MTBC formation assayed; intact or heated saliva obtained from smokers (while smoking or without); 37 deg C; incubated for 0.5-15 min; TBC and MTBC formation determined by HPLC

Further Details (Pharmacological Data)

TBC: 1,2,3,4-tetrahydro-β-carboline; MTBC: 1-methyl-1,2,3,4-tetrahydro-β-carboline

Results

in intact and heated saliva obtained while smoking fromation of TBC and MTBC increased with increasing time of incubation and conc. of title comp.; in saliva obtained from smokers without smoking neither TBC nor MTBC was found

Tsuchiya; Ohtani; Yamada; Tajima; Sato; Biochemical Pharmacology; vol. 50; nb. 12; (1995); p. 2109 - 2112, View in Reaxys 176 of 193 Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

human saliva

Sex

male

Concentration (Pharmacological Data)

2.5 mg/l

Method (Pharmacological Data)

in vitro; TBC and MTBC formation assayed; smoke of single cigarette bubbled through 5 ml of saliva; 37 deg C; incubated for 10 min; TBC and MTBC formation determined by HPLC

Further Details (Pharmacological Data)

TBC: 1,2,3,4-tetrahydro-β-carboline; MTBC: 1-methyl-1,2,3,4-tetrahydro-β-carboline

Results

graphical representation; TBC and MTBC in saliva increased; level of TBC was higher than MTBC; TBC and MTBC conc. were dependent on volume of added smoke saliva

Tsuchiya; Ohtani; Yamada; Tajima; Sato; Biochemical Pharmacology; vol. 50; nb. 12; (1995); p. 2109 - 2112, View in Reaxys 177 of 193 Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

rat C6-glial cells expressing human 5-HT1Dβ receptor

Concentration (Pharmacological Data)

1E-10 - 1E-05 mol/l

Method (Pharmacological Data)

in vitro; inhibition of forskolin-stimulated cAMP formation evaluated; 100 μmol/l forskolin; 1 mmol/l isobutylmethylxanthine; controlled salt solution, pH 7.4; humidified 95 percent air/5 percent CO2; 37 deg C; incubated for 5 min

Further Details (Pharmacological Data)

cellular cAMP content assayed using RIA; EC50: conc. yielding 50 percent of inhibition of forskolin-induced cAMP formation produced by 1 μmol/l 5-HT; Emax: max. percent inhibition of forskolin-induced cAMP formation vs. that obtained with 1 μmol/l 5-HT

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

100 nmol/l

Results

Emax: 96 percent (conc.-response curve)

Pauwels, Petrus J.; Colpaert, Francis C.; Biochemical Pharmacology; vol. 50; nb. 10; (1995); p. 1651 - 1658, View in Reaxys 178 of 193 Comment (Pharmacological Data)

activity against Mycobacterium tuberculosis H 37 Ra, MIC: 256 μg/ml

Mahboobi; Grothus; Meindl; Archiv der Pharmazie; vol. 327; nb. 2; (1994); p. 105 - 114, View in Reaxys 179 of 193 Comment (Pharmacological Data)

antifouling activity

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Kon-Ya, Kazumi; Shimidzu, Nobuyoshi; Miki, Wataru; Endo, Mamoru; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 12; (1994); p. 2178 - 2181, View in Reaxys 180 of 193 Effect (Pharmacological Data)

antimutagenic

Species or Test-System (Pharmacological Data)

Salmonella typhimurium TA 100

Concentration (Pharmacological Data)

0.33 - 10 μmol/plate

Exposure Period (Pharmacological Data)

48 h

Method (Pharmacological Data)

4-nitroquinoline (4-NQO) as mutagenic agent; standard plate incorporation assay; 37 deg C

Further Details (Pharmacological Data)

inhibition of direct-acting mutagenicity of 4-NQO

Comment (Pharmacological Data)

No effect

De Flora; Rosenkranz; Klopman; Mutagenesis; vol. 9; nb. 1; (1994); p. 39 - 45, View in Reaxys 181 of 193 Comment (Pharmacological Data)

receptor binding affinities (pKl) for 6 subtypes of serotonin/tryptamin receptors: 5-HT1A: 7.35; 5-HT1B: 7.32; 5-HT1C: 7.78; 5-HT1D: 7.24; 5-HT2: 5.41; 5-HT3: <5.14; tryptamine: 8.21.

Dijkstra, Gerard D. H.; Tulp, Martin Th. M.; Hermkens, Pedro H. H.; Maarseveen, Jan H. van; Scheeren, Hans W.; Kruse, Chris G.; Recueil des Travaux Chimiques des Pays-Bas; vol. 112; nb. 2; (1993); p. 131 - 136, View in Reaxys 182 of 193 Comment (Pharmacological Data)

competitive inhibitor of L-tryptophan 2',3'-oxidase from Chromobacterium violaceum

Genet, R; Denoyelle, C; Menez, A; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 12; (1992); p. 848 - 850, View in Reaxys 183 of 193 Comment (Pharmacological Data)

LD 50: 276; dose (mg/kg): 92 on male Swiss albino mice

Cingolani; Claudi; Venturi; European Journal of Medicinal Chemistry; vol. 23; nb. 3; (1988); p. 291 - 294, View in Reaxys 184 of 193 Comment (Pharmacological Data)

inhibition of the metabolism by clorgyline or semicarbazide in human umbilical artery

Precious; Lyles; Journal of Pharmacy and Pharmacology; vol. 40; nb. 9; (1988); p. 627 - 633, View in Reaxys 185 of 193 Comment (Pharmacological Data)

in vitro anti-acetylcholine activity ID 50: 46 μg/ml; anti-histamine activity ID 50: 16.3 μg/ml on guinea pig ileum

Cingolani; Claudi; Venturi; European Journal of Medicinal Chemistry; vol. 23; nb. 3; (1988); p. 291 - 294, View in Reaxys 186 of 193 Comment (Pharmacological Data)

toxicity (at 160 mg/kg s.c.) in combination with deltamethrin (1.5 g/kg p.o.) or iproniazid (250 mg/kg p.o.) in white mice (Swiss strain) of either sex

Pham Huu Chanh; Navarro Delmasure Ch.; et al.; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 2; (1984); p. 175 - 181, View in Reaxys 187 of 193 Comment (Pharmacological Data)

effects on syntheses of tyramine oxidase and β-galactosidase in strains with tyn :: lac or ats :: lac fusions (Escherichia coli)

Yamashita, Mitsuo; Murooka, Yoshikatsu; Agricultural and Biological Chemistry; vol. 48; nb. 6; (1984); p. 1459 1470, View in Reaxys 188 of 193 Comment (Pharmacological Data)

no effect on the production of polyamine oxidase by Penicillium sp. No. PO-1

Kobayashi, Yoshinori; Horikoshi, Koki; Agricultural and Biological Chemistry; vol. 45; nb. 12; (1981); p. 2943 2946, View in Reaxys 189 of 193 Comment (Pharmacological Data)

effect on oxidations of putrescine by putrescine oxidase from Micrococcus rubens and spermine by the Penicillium enzyme

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Isobe, Kimiyasu; Tani, Yoshiki; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 45; nb. 3; (1981); p. 727 - 734, View in Reaxys 190 of 193 Comment (Pharmacological Data)

increases the cyclic GMP content in human blood platelets

Laubscher; Pletscher; Journal of Pharmacy and Pharmacology; vol. 32; nb. 8; (1980); p. 601 - 602, View in Reaxys 191 of 193 Comment (Pharmacological Data)

effect on spermine and spermidine oxidation by polyamine oxidase from Penicillium chrysogenum and by polyamine oxidase from Aspergillus terreus

Isobe, Kimiyasu; Tani, Yoshiki; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 44; nb. 12; (1980); p. 2955 - 2960, View in Reaxys 192 of 193 Comment (Pharmacological Data)

Uebersicht ueber d. pharmakologische Wirkung

Daly; Witkop; Angewandte Chemie; vol. 75; (1963); p. 552,558-560, View in Reaxys 193 of 193 Comment (Pharmacological Data)

Zum Metabolismus beim malabsorption syndrom

Haverback et al.; New England Journal of Medicine; vol. 262; (1960); p. 754; Chem.Abstr.; nb. 14429; (1960), View in Reaxys Ecotoxicology (4) 1 of 4

Effect (Ecotoxicology)

toxicity to invertebrates

Species or Test-System (Ecotoxicology)

brine shrimp

Kind of Dosing (Ecotoxi- title comp. dissolved in 20 percent aq. DMSO to 1 mg/ml concentration, formed solution cology) serially diluted two times to seven different concentrations Method (Ecotoxicology)

brine shrimp lethality assay carried out with nauplii; 1 ml title comp. solution of different concentrations transferred into vials and 9 ml aerated seawater added; about 10 nauplii transferred into each vial; number of alive nauplii after 24 h noted

Further Details (Ecotoxi- podophyllotoxin as control with LD50 2.79 mg/l; shrimp eggs hatched in flask with artificial cology) seawater, flask aerated and kept at 29-30 deg C, light source left on, nauplii hatched within 48 h Type (Ecotoxicology)

LD50

Value of Type (Ecotoxicology)

83 mg/l

Effect (Ecotoxicology)

biotransformation

Species or Test-System (Ecotoxicology)

hairy roots of Catharanthus roseus

Concentration (Ecotoxicology)

1 mmol/l

Kind of Dosing (Ecotoxi- on day 7 in DMSO cology) Method (Ecotoxicology)

culture grown at 26 deg C and pH 5.7; extraction and LC-MS on day 21

Comment (Ecotoxicology)

Further metabolite(s)

Metabolite (Ecotoxicology)

serpentine; ajmalicine; Yohimbine

McCoy, Elizabeth; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 128; nb. 44; (2006); p. 14276 - 14277, View in Reaxys 3 of 4

Effect (Ecotoxicology)

biotransformation

Species or Test-System (Ecotoxicology)

Penicillum sp. isolate N934-53

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Kind of Dosing (Ecotoxi- 14C-labeled title comp. (0.14 μCi) dissolved in water and delivered in 4 equal sub-doses cology) at 48, 64, 68 and 72 h Method (Ecotoxicology)

title comp. delivered to test species; culture harvested at 80 h; metabolites isolated by extraction; scintillation counting

Results

title comp. incorporated into communesin alkaloids during biosynthesis; table

Metabolite (Ecotoxicology)

communesin A; communesin B

Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.; Phytochemistry; vol. 67; nb. 6; (2006); p. 561 - 569, View in Reaxys 4 of 4

Effect (Ecotoxicology)

biotransformation

Species or Test-System (Ecotoxicology)

Alangium lamarckii Thw.

Kind of Dosing (Ecotoxi- soln. in H2O-DMSO cology) Method (Ecotoxicology)

<14-C>-label. title comp. fed to young plants by wick feeding technique; H2O added after uptake was complete; plants kept alive for 7-8 d; macerated in EtOH; chromatography

Results

0.16 percent and 0.175 percent radioactivity incorporation into deoxytubulosine and alangimarckine, resp.; biosynthesis sequence: tyrosine -> dopamine -> N-deacetylisoipecoside (-> ahkorine) -> deoxytubulosine -> alangimarckine

Metabolite (Ecotoxicology)

deoxytubulosine; (-)-alangimarckine

Jain, Sudha; Sinha, Archana; Bhakuni, Dewan S.; Phytochemistry; vol. 60; nb. 8; (2002); p. 853 - 859, View in Reaxys Use (21) Laboratory Use and Handling

Use Pattern

Location

References

Pharmaceuticals

Page/Page column 22-30

Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys

activating GPR139

Page/Page column 22-30

Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys

for detecting GPR139 activation

Page/Page column 22-30

Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys

modulating Phenylketonuria (PKU)

Page/Page column 22-30

Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys

modulating a neu- Page/Page colrological function umn 22-30

Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys

A part of composition suitable for improving seed quality in a plant

Page/Page column 38

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116260; (2010); (A2) English, View in Reaxys

thinning agent

Page/Page column Title page; 29

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; DECKERS, Tom; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116256; (2010); (A2) English, View in Reaxys

A part of composition used as a plant safener

Page/Page column 136

Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116264; (2010); (A2) English, View in Reaxys

insect attractant

Page/Page column 23

Patent; ACTIVETRAD (PROPRIETARY) LIMITED; WO2008/110984; (2008); (A1) English, View in Reaxys

pest control composition

Page/Page column 23

Patent; ACTIVETRAD (PROPRIETARY) LIMITED; WO2008/110984; (2008); (A1) English, View in Reaxys

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aryl hydrocarbon receptor binding ligand

Patent; G.I.M.-GESELLSCHAFT FUeR INNOVATIVE MEDIZIN GMBH NFG OHG; EP1842541; (2007); (A1) English, View in Reaxys

endometriosis

Patent; G.I.M.-GESELLSCHAFT FUeR INNOVATIVE MEDIZIN GMBH NFG OHG; EP1842541; (2007); (A1) English, View in Reaxys

antidyslipidemic formulation comprising vanadium (IV)/(V) compounds

Patent; GENMEDICA THERAPEUTICS SL; WO2006/64061; (2006); (A1) English, View in Reaxys

semicarbazidesensitive amine oxidase (SSAO) substrates

Page/Page column 10; 30; 32

Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys

diabetes

Page/Page column 10; 30; 32

Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys

diabetes type 1

Page/Page column 10; 30; 32

Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys

diabetes type 2

Page/Page column 10; 30; 32

Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys

diabetes mellitus

Page/Page column 10; 30; 32

Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys

obesity

Page/Page column 10; 30; 32

Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys

Comparative compound for investigation of inhibition of lipid peroxidation used as inhibitor in reaction of peroxidation of 1stearoyl 2-linoleoyl sn-glycerol 3phosphocholine induced by FeCl2*4H2O

Patent; Board of Trustees of Michigan State University; US2005/59727; (2005); (A1) English, View in Reaxys

Jayaprakasam, Bolleddula; Strasburg, Gale A.; Nair, Muraleedharan G.; Tetrahedron; vol. 60; nb. 13; (2004); p. 3109 - 3121, View in Reaxys

Isolation from Natural Product (24) Isolation from References Natural Product Penicillium sp. CYE-87; isolated from Didemnum sp., marine tunicate; collected from Suez Canal, Egypt, around a man-made support at a depth of 1–2 m in July 2010

Shaala, Lamiaa A.; Youssef, Diaa T. A.; Marine Drugs; vol. 13; nb. 4; (2015); p. 1698 - 1709, View in Reaxys

South China Sea Qi, Shu-Hua; Miao, Li; Gao, Cheng-Hai; Xu, Ying; Zhang, Si; Qian, Pei-Yuan; Helvetica Chimica Acta; gorgonian coral vol. 93; nb. 3; (2010); p. 511 - 516, View in Reaxys Isis minorbrachyblasta collected in Sanya, Hainan Province, China, in May 2007 leaves, flowers, stems and aerial parts of Prosopis

139/155

2016-06-21 14:42:30

glandulosa Torrey var. glandulosa (Leguminosae); collected from Nevada Chimonanthus Kitajima, Mariko; Mori, Ikue; Arai, Kazumichi; Kogure, Noriyuki; Takayama, Hiromitsu; Tetrahedron Letpraecox f. concol- ters; vol. 47; nb. 19; (2006); p. 3199 - 3202, View in Reaxys or Makino (Calycanthaceae); seeds and rinds seeds of Centaur- Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji; Nahar, Lutfun; Kongea montana Thoo-Lin, Paul; Sarker, Satyajit D.; Tetrahedron; vol. 62; nb. 48; (2006); p. 11172 - 11177, View in Reaxys Didemnum sp. Segraves, Nathaniel L.; Robinson, Sarah J.; Garcia, Daniel; Said, Sadri A.; Fu, Xiong; Schmitz, Francis Monniot and Mon- J.; Pietraszkiewicz, Halina; Valeriote, Frederick A.; Crews, Phillip; Journal of Natural Products; vol. 67; niot 1997, tuninb. 5; (2004); p. 783 - 792, View in Reaxys cate, collected in Northern Sulawesi, Indonesia marine sponge Smenospongia sp. (Thorectidae)

McKay, Matthew J.; Carroll, Anthony R.; Quinn, Ronald J.; Hooper, John N. A.; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 595 - 597, View in Reaxys

sponge (PAL93-055)

Patil, Ashok D.; Freyer, Alan J.; Carte, Brad; Taylor, Paul B.; Johnson, Randall K.; Faulkner, D. John; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 628 - 629, View in Reaxys

culture of Rauvol- Sheludko; Gerasimenko; Platonova; Planta Medica; vol. 66; nb. 7; (2000); p. 656 - 659, View in Reaxys fia serpentina Benth. ex Kurz * Rhazya stricta Decaisne (Apocynaceae), RxR17K callus strain stimulated with 100 μM methyl jasmonate aerial part of Nitraria schoberi L.

Tulyaganov; Nazarov; Chemistry of Natural Compounds; vol. 36; nb. 4; (2000); p. 393 - 395, View in Reaxys

Villagorgia rubra

Espada, Alfonso; Tetrahedron Letters; vol. 34; nb. 48; (1993); p. 7773 - 7776, View in Reaxys

epigeal part of Ni- Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh traria komarovii Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys leaves of Tecoma stans

Kunapuli, Satya P.; Vaidyanathan, C. S.; Phytochemistry (Elsevier); vol. 23; nb. 8; (1984); p. 1826 - 1827, View in Reaxys

aus Desmodium tiliaefolium

Ghosal; Srivastava; Phytochemistry (Elsevier); vol. 12; (1973); p. 193,196, View in Reaxys

Vork. u. Isol. aus Acacia caesia

Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

Vork. u. Isol. aus Acacia leucophloea

Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

Vork. u. Isol. aus Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys Acacia farnesiana Vork. u. Isol. aus Desmodium triflorum

Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

aus Petalostylis Labicheoides

Johns et al.; Australian Journal of Chemistry; vol. 19; (1966); p. 893, View in Reaxys

Abtrennung v. Indol-Derivaten aus Urin mittels Sephadex G25

Schlossberger et al.; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 333; (1963); p. 152, View in Reaxys

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Ausscheidung im Urin nach Eingabe v. versch. Drogen

Svoerdsma et al.; Proceedings of the Society for Experimental Biology and Medicine; vol. 103; (1960); p. 485; Chem.Abstr.; vol. 54; nb. 13415; (1960), View in Reaxys

aus Acacia podalyriifolia

White; New Zealand J. Sci. Technol. <B>; vol. 33; (1951); p. 54,60, View in Reaxys

aus Acacia floriWhite; New Zealand J. Sci. Technol. <B>; vol. 25; (1944); p. 137,158, View in Reaxys bunda und Acacia pruinosa bei der VergaerGrimmer; Wiemann; Forschg. Milchwirtsch. Molkereiw.; vol. 1; p. 2; Chem. Zentralbl.; vol. 92; nb. I; (1921); ung von Casein p. 775, View in Reaxys durch Bac. mesentericus vulgatus

Reaxys ID 3568419 View in Reaxys

2/2 CAS Registry Number: 343-94-2 Chemical Name: tryptamine hydochloride; 3-(2-aminoethyl)indole hydrochloride; Tryptamine hydrochloride; tryptamine hydrochloride; tryptamine monohydrochloride; triptamine hydrochloride; tryptamine hydrochloide Linear Structure Formula: C10H13N2 (1+)*Cl(1-) Molecular Formula: C10H13N2*Cl Molecular Weight: 196.68 Type of Substance: heterocyclic InChI Key: KDFBGNBTTMPNIG-UHFFFAOYSA-N Note:

H NH

NH 2

Substance Label (24) Label References 7

Arazny; Czarnocki; Wojtasiewicz; Maurin; Tetrahedron Asymmetry; vol. 11; nb. 13; (2000); p. 2793 - 2800, View in Reaxys; Gattuso, Giuseppe; Notti, Anna; Parisi, Melchiorre F.; Pisagatti, Ilenia; Marcos, Paula Maria; Ascenso, Jos Rosrio; Brancatelli, Giovanna; Geremia, Silvano; New Journal of Chemistry; vol. 39; nb. 2; (2015); p. 817 - 821, View in Reaxys

1*HCl

Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys; Mizoguchi, Haruki; Oikawa, Hideaki; Oguri, Hiroki; Nature Chemistry; vol. 6; nb. 1; (2014); p. 57 - 64, View in Reaxys

Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys; Takasu, Kiyosei; Shimogama, Tsubasa; Saiin, Chalerm; Kim, HyeSook; Wataya, Yusuke; Ihara, Masataka; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 7; (2004); p. 1689 - 1692, View in Reaxys; Takasu, Kiyosei; Shimogama, Tsubasa; Saiin, Chalerm; Kim, Hye-Sook; Wataya, Yusuke; Brun, Reto; Ihara, Masataka; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 6; (2005); p. 653 - 661, View in Reaxys; Reimer, Daniela; Nollmann, Friederike I.; Schultz, Katharina; Kaiser, Marcel; Bode, Helge B.; Journal of Natural Products; vol. 77; nb. 8; (2014); p. 1976 - 1980, View in Reaxys

Li, Yuexian; Prakash, Shimoga R.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 5; (2005); p. 323 - 330, View in Reaxys; Fischereder, Eva; Pressnitz, Desiree; Kroutil, Wolfgang; Lutz, Stefan; Bioorganic and Medicinal Chemistry; vol. 22; nb. 20; (2014); p. 5633 - 5637, View in Reaxys

Tian, Jingjing; Du, Qiuchen; Guo, Rui; Li, Yun; Cheng, Bin; Zhai, Hongbin; Organic Letters; vol. 16; nb. 12; (2014); p. 3173 - 3175, View in Reaxys

TRY

Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys

Panosyan; Still; Canadian Journal of Chemistry; vol. 79; nb. 7; (2001); p. 1110 - 1114, View in Reaxys; Panarese, Joseph D.; Waters, Stephen P.; Organic and Biomolecular Chemistry; vol. 11; nb. 21; (2013); p. 3428 - 3431, View in Reaxys

Eschenbrenner-Lux, Vincent; Dueckert, Heiko; Khedkar, Vivek; Bruss, Hanna; Waldmann, Herbert; Kumar, Kamal; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2294 - 2304, View in Reaxys

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Sanaboina, Chakrapani; Jana, Samaresh; Chidara, Sridhar; Patro, Balaram; Raolji, Gajendrasinh Balvantsinh; Eppakayala, Laxminarayana; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 5027 - 5029,3, View in Reaxys

Miyake, Fumiko Y.; Yakushijin, Kenichi; Horne, David A.; Organic Letters; vol. 6; nb. 5; (2004); p. 711 713, View in Reaxys; Nemet, Ina; Varga-Defterdarovic, Lidija; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4551 - 4562, View in Reaxys

Shen, Shuren; Bremont, Beatrice; Serraz, Isabelle; Andrieux, Jean; Poncet, Annie; Mathe-Allainmat, Monique; Chanut, Evelyne; Trouvin, Jean-Hugues; Langlois, Michel; European Journal of Pharmacology; vol. 307; nb. 2; (1996); p. 133 - 140, View in Reaxys; Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys; Molt, Oliver; Ruebeling, Daniel; Schaefer, Gerhard; Schrader, Thomas; Chemistry - A European Journal; vol. 10; nb. 17; (2004); p. 4225 - 4232, View in Reaxys; Fokas, Demosthenes; Wang, Zhimin; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3816 - 3822, View in Reaxys

Tonkikh; Strakovs; Petrova; Chemistry of Heterocyclic Compounds; vol. 41; nb. 8; (2005); p. 1053 - 1058, View in Reaxys; Tulyaganov; Kozimova; Allaberdiev; Chemistry of Natural Compounds; vol. 42; nb. 2; (2006); p. 198 - 200, View in Reaxys

2e*HCl

Pal, Bikash; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 34; nb. 7; (2004); p. 1317 - 1323, View in Reaxys

2a; 4a; 5a

Patent; ELI LILLY AND COMPANY; EP942722; (2004); (B1) English, View in Reaxys

Itoh, Atsuko; Tanahashi, Takao; Nagakura, Naotaka; Nishi, Toyoyuki; Phytochemistry; vol. 62; nb. 3; (2003); p. 359 - 369, View in Reaxys

Fokas, Demosthenes; Patterson, Jean E.; Slobodkin, Gregory; Baldino, Carmen M.; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5137 - 5140, View in Reaxys

2f*HCl

Strakovs; Tonkikh; Petrova; Ryzhanova; Palitis; Chemistry of Heterocyclic Compounds; vol. 38; nb. 4; (2002); p. 449 - 455, View in Reaxys

1, R=R1=R2=H

Novak; Hanania; Kovacs; Kolonits; Szantay; Synthesis; nb. 1; (2001); p. 108 - 118, View in Reaxys

Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; Photochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, View in Reaxys

Tulyaganov; Nazarov; Levkovich; Abdullaev; Chemistry of Natural Compounds; vol. 37; nb. 1; (2001); p. 61 - 64, View in Reaxys

7*HCl

Bringmann, Gerhard; Feineis, Doris; Brueckner, Ralph; Blank, Michael; Peters, Karl; Peters, Eva-Maria; Reichmann, Heinz; Janetzky, Bernd; Grote, Christoph; Clement, Hans-Willi; Wesemann, Wolfgang; Bioorganic and Medicinal Chemistry; vol. 8; nb. 6; (2000); p. 1467 - 1478, View in Reaxys

Herr; Kuhler; Meckler; Opalka; Synthesis; nb. 11; (2000); p. 1569 - 1574, View in Reaxys

Tietze, Lutz F.; Zhou, Yifa; Toepken, Enno; European Journal of Organic Chemistry; nb. 12; (2000); p. 2247 - 2252, View in Reaxys

1a*HCl

Patthy-Lukats, Agnes; Kocsis, Akos; Szabo, Laszlo F.; Podanyi; Journal of Natural Products; vol. 62; nb. 11; (1999); p. 1492 - 1499, View in Reaxys

Patent-Specific Data (2) References Patent; NATREON, INC.; Ghosal, Shibnath; Veeraragavan, Muruganandam; Kalidindi, Sanyasi R.; US2013/115316; (2013); (A1) English, View in Reaxys Patent; Les Laboratoires Servier; US6350757; (2002); (B1) English, View in Reaxys Melting Point (10) 1 of 10

Melting Point [°C]

245 - 248

Solvent (Melting Point)

ethanol

Location

supporting information

Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 2 of 10

Melting Point [°C]

247 - 248

Solvent (Melting Point)

aq. ethanol; ethyl acetate

Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys

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3 of 10

Melting Point [°C]

251 - 253

Solvent (Melting Point)

ethanol; ethyl acetate

Melting Point [°C]

256

Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi; Chemistry Letters; (1986); p. 893 - 896, View in Reaxys 5 of 10

Melting Point [°C]

248 - 249

Solvent (Melting Point)

ethanol; ethyl acetate

Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 21; nb. 4; (1985); p. 502 - 509; Khimiya Prirodnykh Soedinenii; vol. 21; nb. 4; (1985); p. 536 - 544, View in Reaxys 6 of 10

Melting Point [°C]

248 - 249

Tulyaganov, T. S.; Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 17; (1981); p. 149 152; Khimiya Prirodnykh Soedinenii; vol. 17; nb. 2; (1981); p. 192 - 195, View in Reaxys 7 of 10

Melting Point [°C]

250 - 252

Solvent (Melting Point)

ethanol; diethyl ether

Brutcher; Vanderwerff; Journal of Organic Chemistry; vol. 23; (1958); p. 146, View in Reaxys 8 of 10

Melting Point [°C]

249 - 250

Solvent (Melting Point)

methanol; ethyl acetate

Comment (Melting Point)

Decomp.

Young; Journal of the Chemical Society; (1958); p. 3493,3494, View in Reaxys 9 of 10

Melting Point [°C]

248

Manske; Journal of the American Chemical Society; vol. 51; (1929); p. 1203; Canadian Journal of Research; vol. 4; (1931); p. 594; Chem. Zentralbl.; vol. 102; nb. II; (1931); p. 2738, View in Reaxys 10 of 10

Melting Point [°C]

251 - 253

Jackson; Journal of Biological Chemistry; vol. 84; (1929); p. 5, View in Reaxys Association (MCS) (5) 1 of 5

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

D2O

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

temperature dependence

Partner (Association (MCS))

2,19,28,45-tetraoxa-3,18,29,44-tetraoxo-10,36-diyne-22,25,48,51-tetrakis(dimethoxyphosphorylmethyl)-[3.2.3.2]paracyclophane tetralithium salt

Molt, Oliver; Ruebeling, Daniel; Schaefer, Gerhard; Schrader, Thomas; Chemistry - A European Journal; vol. 10; nb. 17; (2004); p. 4225 - 4232, View in Reaxys 2 of 5

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

D2O

Comment (Association (MCS))

ambient temperature

Partner (Association (MCS))

2,19,28,45-tetraoxa-3,18,29,44-tetraoxo-10,36-diyne-22,25,48,51-tetrakis(dimethoxyphosphorylmethyl)-[3.2.3.2]paracyclophane tetralithium salt

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Molt, Oliver; Ruebeling, Daniel; Schaefer, Gerhard; Schrader, Thomas; Chemistry - A European Journal; vol. 10; nb. 17; (2004); p. 4225 - 4232, View in Reaxys 3 of 5

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

aq. phosphate buffer

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

5,10,15,20-tetrakis(4-methylpyridinium)porphyrin tetrahydrochloride

Rekharsky; Nakamura; Hembury; Inoue; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 449 457, View in Reaxys 4 of 5

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

methanol

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

3,10-dimethyl-1',4',7',10',13',16'-hexaoxacyclooctadec-2'-enolt;2',3'-igt;isoalloxazine; K(1+)

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

methanol

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

3-methyllumiflavin; K(1+)

Shinkai, Sheiji; Ishikawa, Yuichi; Shinkai, Hiroko; Tsuno, Takaharu; Makishima, Hiroki; et al.; Journal of the American Chemical Society; vol. 106; nb. 6; (1984); p. 1801 - 1808, View in Reaxys Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Fischereder, Eva; Pressnitz, Desiree; Kroutil, Wolfgang; Lutz, Stefan; Bioorganic and Medicinal Chemistry; vol. 22; nb. 20; (2014); p. 5633 - 5637, View in Reaxys; Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties brown

supporting information

References Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 2700, View in Reaxys

NMR Spectroscopy (9) 1 of 9

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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Location

supporting information

Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 2 of 9

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- water-d2 scopy) Location

supporting information

Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 3 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

δH 2.97 2H t J=9, 3.13 2H t J=8, 7.01 1H t J=4, 7.07-7.12 2H m, 7.34 1H d J=4, 7.49 1H d J=4;

Location

Paragraph 0053

Patent; Morrison, Richard W.; Jackson, Douglas Michael; US2014/275569; (2014); (A1) English, View in Reaxys 4 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- water-d2 scopy) Original Text (NMR Spectroscopy)

δC 22.88, 40.03, 109.36, 112.30, 118.54, 119.68, 122.44, 124.53, 126.70, 136.69

Location

Paragraph 0053

Patent; Morrison, Richard W.; Jackson, Douglas Michael; US2014/275569; (2014); (A1) English, View in Reaxys 5 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Teuber, Hans-Joachim; Quintanilla-Licea, Ramiro; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 336; nb. 5; (1994); p. 452 - 457, View in Reaxys 6 of 9

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Teuber, Hans-Joachim; Quintanilla-Licea, Ramiro; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 336; nb. 5; (1994); p. 452 - 457, View in Reaxys

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7 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Saito; Muramatsu; Sugiyama; et al.; Tetrahedron Letters; vol. 26; nb. 48; (1985); p. 5891 - 5894, View in Reaxys 8 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Ernst, Ludger; Kang, Sungzong; Journal of Chemical Research, Miniprint; nb. 9; (1981); p. 3019 - 3038, View in Reaxys 9 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6; trifluoroacetic acid scopy) Temperature (NMR Spectroscopy) [°C]

Ernst, Ludger; Kang, Sungzong; Journal of Chemical Research, Miniprint; nb. 9; (1981); p. 3019 - 3038, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3333 - 1250 cm**(-1)

Nakanishi et al.; Bulletin of the Chemical Society of Japan; vol. 30; (1957); p. 403,405, View in Reaxys Mass Spectrometry (3) Description (Mass References Spectrometry) liquid chromatog- Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of raphy mass spec- Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys trometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; spectrum liquid chromatog- Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of raphy mass spec- Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys trometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; IT (ion trap); spectrum LCMS (Liquid chromatography mass spectrometry); Tandem mass spectrome-

Sagratini; Fernandez-Franzon; De Berardinis; Font; Vittori; Manes; Food Chemistry; vol. 132; nb. 1; (2012); p. 537 - 543, View in Reaxys

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2016-06-21 14:42:30

try; ESI (Electrospray ionisation); Spectrum UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

methanol

Comment (UV/VIS Spectroscopy)

300 - 600 nm

Hayakawa, Kenji; Kido, Keiko; Kanematsu, Ken; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 511 - 520, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Absorption Maxima (UV/ 221; 275; 281; 290 VIS) [nm] Noland; Hartman; Journal of the American Chemical Society; vol. 76; (1954); p. 3227, View in Reaxys Luminescence Spectroscopy (1) Description (LuReferences minescence Spectroscopy) Luminescence lifetime

Shizuka, Haruo; Serizawa, Manabu; Kobayashi, Hirokazu; Kameta, Kosei; Sugiyama, Hiroshi; et al.; Journal of the American Chemical Society; vol. 110; nb. 6; (1988); p. 1726 - 1732, View in Reaxys

Fluorescence Spectroscopy (5) Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)

Comment (Fluorescence Spectroscopy)

References

Fluorescence

Medici, Rosario; De Maria, Pablo Dominguez; Otten, Linda G.; Straathof, Adrie J. J.; Advanced Synthesis and Catalysis; vol. 353; nb. 13; (2011); p. 2369 - 2376, View in Reaxys

Maxima

benzene

Maxima

H2O

Fluorescence quantum yield Maxima

in the presence of Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; organic comPhotochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, pounds View in Reaxys Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; Photochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, View in Reaxys in the presence of Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; organic comPhotochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, pounds View in Reaxys

H2O

355 nm

Sprince et al.; Science (Washington, DC, United States); vol. 125; (1957); p. 442, View in Reaxys; Bertrand; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 1023,1025, View in Reaxys

Pharmacological Data (11) 1 of 11

Comment (Pharmacological Data)

Bioactivities present

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Comment (Pharmacological Data)

physiological behaviour discussed

Shimizu, Mai; Fukami, Tatsuki; Nakajima, Miki; Yokoi, Tsuyoshi; Drug Metabolism and Disposition; vol. 42; nb. 7; (2014); p. 1103 - 1109, View in Reaxys 3 of 11

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing rat 5-HT6 receptors

Concentration (Pharmacological Data)

Ca. 1E-10 - 1E-06 mol/l

Method (Pharmacological Data)

0.2 nmol/l <35S>GTPγS used as radioligand; 20 mmol/l HEPES buffer (pH 7.4), 1 h; Gα activation determined by SPA/antibody-immunocapture procedure; non-specific binding defined at 10 μmol/l GTPγS

Further Details (Pharmacological Data)

serotonin (5-HT) used for comparison (pEC50: 7.69; Emax at 1 μmol/l=100percent); SPA: scintillation proximity assay

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

6.13 dimensionless

Results

title comp. stimulated binding <35S>GTPγS to Gα proteins with Emax=109.8percent, thus acting as full agonist; fig.

Dupuis, Delphine S.; la Cour, Clotilde Mannoury; Chaput, Christine; Verriele, Laurence; Lavielle, Gilbert; Millan, Mark J.; European Journal of Pharmacology; vol. 588; nb. 2-3; (2008); p. 170 - 177, View in Reaxys 4 of 11

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing rat 5-HT6 receptors

Concentration (Pharmacological Data)

Ca. 1E-09 - 0.0001 mol/l

Method (Pharmacological Data)

radioligand binding assay; 0.1 nmol/l <125I>SB258,585 used as radioligand; 50 mmol/l Tris (pH 7.4) buffer, 37 deg C, 45 min; non-specific binding defined with 10 μmol/l methiothepin

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Further Details (Pharmacological Data)

5-HT: serotonin

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

5.94 dimensionless

Results

title comp. showed high affinity for 5-HT6 receptors; fig.

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK cell membranes

Method (Pharmacological Data)

radioligand binding assay; in triplicate; assay tubes containing membranes, 2.5 nmol/l <3H>5-HT and varying concentrations of title comp. incubated for 20 min at 37 deg C; suspensions filtered and counted in liquid scintillation counter

Further Details (Pharmacological Data)

HEK cells stably expressing human 5-HT1E receptor; methiothepin (10 μmol/l) used to define nonspecific binding; 5-HT, serotonin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

500 nmol/l

Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys 6 of 11

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

COS-7 cells

Method (Pharmacological Data)

h5-HT6 radioligand binding assay; 5-HT6-cDNA transfected by DEAE-dextran technique, harvested (centrifugated/washed) cells suspended in Tris-Cl/MgCl2/EDTA buffer (pH 7.40), room temp., 90 min, 1 nmol/l <3H>LSD, 10 μmol/l clozapine, title comp.

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

180 nmol/l

Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys 7 of 11

Effect (Pharmacological Data)

neuromuscular

Species or Test-System (Pharmacological Data)

Hartley guinea pig

Sex

male

Route of Application

inhalation

Concentration (Pharmacological Data)

0.001 - 0.01 percent

Kind of Dosing (Pharmacological Data)

through ultrasonic nebulizer

Method (Pharmacological Data)

350-820 g guinea pigs (12 h light:dark cycle) anesthetized; trachea transected; artificially ventilated through respirator; bronchial pressure measured as ventilation overflow (VO) through pneumotachograph

Further Details (Pharmacological Data)

tracheal pressure (TP) measured via pressure transducer; title comp. effect on VO, TP studied

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Results

VO increased; biphasic effect on TP: initial increase, then (3 min later) decrease (diagram)

Takahashia, Yoshinori; Ohno, Hiromitsu; Misawa, Miwa; European Journal of Pharmacology; vol. 302; nb. 1-3; (1996); p. 89 - 97, View in Reaxys 8 of 11

Effect (Pharmacological Data)

inhibition of 5-HT uptake

Species or Test-System (Pharmacological Data)

Wistar rats

Sex

male and female

Concentration (Pharmacological Data)

2900 - 5490 nmol/l

Exposure Period (Pharmacological Data)

22 min

Method (Pharmacological Data)

rats pretreated with pargyline (75 mg/kg i.p.) 18 and 2 h prior sacrifice; in anaesthesia thorax opened, heparin (2500 U/kg) injected intracardially; trachea, pulmonary artery, left atrium cannulated; perfusion via pulmonary artery

Further Details (Pharmacological Data)

lungs perfused with title compd. for 20 min and for 2 min with (3)H-5-HT (2 nmol/l) and (14)C-sorbitol (100 μmol/l); lungs homogenate supernatant and perfusion solution collected from pulmonary artery cannula; (3)H and (14)C content detd.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

4080 nmol/l

Results

title compd. inhibited uptake of 5-HT in perfused lung

Paczkowski, Natalii J.; Vuocolo, Helen E.; Bryan-Lluka, Lesley J.; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 4; (1996); p. 423 - 430, View in Reaxys 9 of 11

Effect (Pharmacological Data)

binding to microsome; effect on

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat liver microsomes

Sex

male

Concentration (Pharmacological Data)

0.01 - 50 μmol/l

Method (Pharmacological Data)

rats (2 - 3 months old), liver microsomes isolated; microsomal suspension treated with <3H>labelled stanozolol overnight at O deg C in the presence of increasing conc. of title comp.; DCC added, centrifuged; supernatant radioactivity counting

Further Details (Pharmacological Data)

DCC = Dextran T70-coated charcoal; protein conc. in microsomal susp. = 2 - 3 mg/ml; ability of the title comp. to compete with <3H>labelled stanozolol for its binding to liver microsomes tested

Comment (Pharmacological Data)

No effect

Boada, Luis D.; Fernandez, Leandro; Zumbado, Manuel; Luzardo, Octavio P.; Chirino, Ricardo; Diaz-Chico, Bonifacio N.; Journal of Pharmacology and Experimental Therapeutics; vol. 279; nb. 3; (1996); p. 1123 - 1129, View in Reaxys 10 of 11

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Dunkin-Hartley guineapig proximal colon

Sex

male and female

Concentration (Pharmacological Data)

1E-06 - 0.001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in distilled H2O

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Method (Pharmacological Data)

pig (400-600 g) killed; proximal colon removed; relaxation induced by title comp. in presence of ketanserin and tropisetron (to block contractions mediated by 5-HT2A,3,4 receptors) and strips precontracted with methacholine

Further Details (Pharmacological Data)

concentration-relaxation curve; relaxation expressed as percentage of relaxation induced by 10 μM 5-hydroxytryptamine

Results

title comp. active as partial agonist: induced relaxation with low potency and efficacy and pEC50 = 5.5

Briejer, Michel R.; Akkermans, Louis M. A.; Lefebvre, Romain A.; Schuurkes, Jan A. J.; European Journal of Pharmacology; vol. 279; nb. 2-3; (1995); p. 123 - 134, View in Reaxys 11 of 11

Comment (Pharmacological Data)

antiproliferative effect against the murine leukemic cell line P388D1; D 50: 58 μM

Laske; Schonenberger; Holler; Archiv der Pharmazie; vol. 322; nb. 12; (1989); p. 857 - 862, View in Reaxys Transport and Distribution (1) 1 of 1

Type (Transport and Distribution)

partition

Media (Transport and Distribution)

water-micellar interface

Results

partition constant K = 10-16

Method, Remarks (Transport and Distribution)

reverse micellar solution containing benzylhexadecyldimethylammonium chloride; title comp. dissolved in water; varying water/surfactant molar ratio; mixtures shaken of sonicated for a few min

Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; Photochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, View in Reaxys

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