1-(3-Methoxyphenyl)cyclohexan-1-amine (3-MeO-PCA) [C13H19NO]

Query Query

1. Query O

Results

Date

2 substances in Reaxys

2018-07-31 10h:36m:12s (UTC)

H 2N

Search as: As drawn ))

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Reaxys ID 3650932 View in Reaxys

O

1/2 CAS Registry Number: 125802-07-5 Chemical Name: 1-(3-methoxyphenyl)cyclohexan-1-amine; {1-[3(methyloxy)phenyl]cyclohexyl}amine; 1-(3-methoxyphenyl)-cyclohexylamine Linear Structure Formula: C13H19NO Molecular Formula: C13H19NO Molecular Weight: 205.3 Type of Substance: isocyclic InChI Key: HCAWFOVQBDALEZ-UHFFFAOYSA-N Note:

H 2N

Substance Label (5) Label References 58

Patent; JORTAN PHARMACEUTICALS INC.; ANKALA, Sudha V.; LILLY, John C.; PEDDABUDDI, Gopal; (180 pag.); WO2017/66742; (2017); (A1) English, View in Reaxys

S19

Xu, Fan; Qian, Xiang-Yang; Li, Yan-Jie; Xu, Hai-Chao; Organic Letters; vol. 19; nb. 23; (2017); p. 6332 - 6335, View in Reaxys

F41

Patent; GLAXO GROUP LIMITED; WO2004/50619; (2004); (A1) English, View in Reaxys

9

Haradahira, Terushi; Sasaki, Sigeki; Maeda, Minoru; Kobayashi, Kaoru; Inoue, Osamu; Tomita, Urara; Nishikawa, Toru; Suzuki, Kazutoshi; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 41; nb. 9; (1998); p. 843 - 858, View in Reaxys

19 free base

Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.; Journal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.64

H Bond Donors

1

H Bond Acceptors

1

Rotatable Bonds

2

TPSA

35.25

Lipinski Number

4

Veber Number

2

Derivative (1) Derivative

References

1-(3-methoxyphen- Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.; yl)-cyclohexylaJournal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys mine hydrochloride Crystal Property Description (2) Colour & Other Location Properties

References

colourless

Paragraph 0198

yellow

supporting informa- Xu, Fan; Qian, Xiang-Yang; Li, Yan-Jie; Xu, Hai-Chao; Organic Letters; vol. 19; nb. 23; tion (2017); p. 6332 - 6335, View in Reaxys

Patent; JORTAN PHARMACEUTICALS INC.; ANKALA, Sudha V.; LILLY, John C.; PEDDABUDDI, Gopal; (180 pag.); WO2017/66742; (2017); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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2018-07-31 10:50:20

Xu, Fan; Qian, Xiang-Yang; Li, Yan-Jie; Xu, Hai-Chao; Organic Letters; vol. 19; nb. 23; (2017); p. 6332 - 6335, View in Reaxys 2 of 2

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 101 scopy) [MHz] Location

supporting information

Xu, Fan; Qian, Xiang-Yang; Li, Yan-Jie; Xu, Hai-Chao; Organic Letters; vol. 19; nb. 23; (2017); p. 6332 - 6335, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Xu, Fan; Qian, Xiang-Yang; Li, Yan-Jie; Xu, Hai-Chao; Organic Letters; vol. 19; nb. 23; (2017); p. 6332 - 6335, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); time-offlight mass spectra (TOFMS); spectrum

Comment (Mass Spectrometry)

supporting information

ESI (Electrospray ionisation)

References Xu, Fan; Qian, Xiang-Yang; Li, Yan-Jie; Xu, Hai-Chao; Organic Letters; vol. 19; nb. 23; (2017); p. 6332 - 6335, View in Reaxys

Molecular peak

Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); (A1) English, View in Reaxys

Molecular peak

Patent; GLAXO GROUP LIMITED; WO2004/50619; (2004); (A1) English, View in Reaxys

Medchem (1) 1 of 1

Target Name

Glutamate receptor ionotropic, NMDA 2D

Target Synonyms

eb11; glun2d; glutamate; glutamate receptor ionotropic, nmda 2d; grin2d; n-methyl d-aspartate receptor subtype 2d; nmdar2d; nr2d

Target, Subunit, Species

Glutamate receptor ionotropic, NMDA 2D

Target Mutant/Chimera Details

Glutamate receptor ionotropic, NMDA 2D:Wild

Substance Action on Target

Radioligand (/ligand)

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Binding affinity of the compound towards NMDA receptor

Substance RN

3650932View in Reaxys

Measurement Parameter

Ki (inhibition constant)

Unit

µM

Qualitative value

=

Quantitative value

0.563

Measurement pX

6.25

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

3/5

2018-07-31 10:50:20

Reaxys ID 3634378 View in Reaxys

2/2

Cl

CAS Registry Number: 125802-06-4 Chemical Name: 1-(3-methoxyphenyl)-cyclohexylamine hydrochloride Linear Structure Formula: C13H19NO*ClH Molecular Formula: C13H19NO*ClH Molecular Weight: 241.761 Type of Substance: isocyclic InChI Key: NKLOFEKZVVGNHB-UHFFFAOYSA-N Note:

H

H 2N

O

Substance Label (1) Label References 19

Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.; Journal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.152

H Bond Donors

1

H Bond Acceptors

1

Rotatable Bonds

2

TPSA

35.25

Lipinski Number

4

Veber Number

2

Melting Point (1) 1 of 1

Melting Point [°C]

195 - 196

Solvent (Melting Point)

ethyl acetate

Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.; Journal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray ionisation)

Patent; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); (A1) English, View in Reaxys

Molecular peak

Medchem (3) 1 of 3

Target Name

Ionotropic glutamate NMDA receptor [rat]

Target Synonyms

ionotropic glutamate nmda receptor

Target, Subunit, Species

Ionotropic glutamate NMDA receptor [rat]

Target Mutant/Chimera Details

Ionotropic glutamate NMDA receptor [rat]:Wild

Target Species (Bioactivity)

rat

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Binding

Biological Species/NCBI ID

rat

Organs/Tissues

brain

Cell Fraction

Membrane

Substance RN

3634378View in Reaxys

Substance Name

Cpd 19

Measurement Parameter

Ki (inhibition constant)

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4/5

2018-07-31 10:50:20

Unit

nM

Quantitative value

563

Measurement pX

6.25

Concomitants: Compound RN

1246605; 1246605

Concomitants: Compound name

TCP; [3H]-TCP

Concomitants: Compound role

NSB; RAD

Thurkauf; De Costa; Yamaguchi; Mattson; Jacobson; Rice; Rogawski; Journal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys 2 of 3

Bioassay Category

In Vivo (Animal models)

Bioassay Name

Inverted Screen

Biological Species/NCBI ID

Swiss Webster mouse

Substance RN

3634378View in Reaxys

Substance Name

Cpd 19

Measurement Parameter

ED50

Unit

mg/kg

Measurement Object

Motor activity

Quantitative value

21.4

Thurkauf; De Costa; Yamaguchi; Mattson; Jacobson; Rice; Rogawski; Journal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys 3 of 3

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Biological Species/NCBI ID

Swiss Webster mouse

Substance RN

3634378View in Reaxys

Substance Name

Cpd 19

Substance Route of Adm.

intraperitoneal administration

Substance Dosing Regimen

Single

Measurement Parameter

ED50

Unit

mg/kg

Measurement Object

Anticonvulsant activity

Quantitative value

14.78

Thurkauf; De Costa; Yamaguchi; Mattson; Jacobson; Rice; Rogawski; Journal of Medicinal Chemistry; vol. 33; nb. 5; (1990); p. 1452 - 1458, View in Reaxys

Copyright Š 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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