2-(Methylamino)-2-phenylcyclohexan-1-one (Deschloroketamine; DXE; DCK; 2'-Oxo-PCM)

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4 substances in Reaxys

2018-05-24 07h:45m:56s (UTC)

O

1. Query HN

Search as: As drawn ))

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Reaxys ID 26423242 View in Reaxys

1/4 Linear Structure Formula: C12 (11)CH17NO Molecular Formula: C13H17NO Molecular Weight: 202.273 InChI Key: ZAGBSZSITDFFAF-BJUDXGSMSA-N Note:

O

HN H 11 3 C

Druglikeness (1) 1 of 1

LogP

2.26

H Bond Donors

1

H Bond Acceptors

2

Rotatable Bonds

2

TPSA

29.1

Lipinski Number

4

Veber Number

2

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

Dissociation constant of compound towards N-methyl-D-aspartate receptor (NMDAR) was determined

Substance RN

26423242View in Reaxys

Measurement Parameter

Kd (dissociation constant)

Unit

nM

Qualitative value

=

Quantitative value

1200

Measurement pX

5.92

Medchem (1) 1 of 1

Reaxys ID 2807399 View in Reaxys

2/4 CAS Registry Number: 7063-30-1 Chemical Name: 2-methylamino-2-phenylcyclohexanone; deschloroketamine; 2-Methylamino-2-phenyl-cyclohexanon; 2-Methylamino-2phenylcyclohexanon Linear Structure Formula: C13H17NO Molecular Formula: C13H17NO Molecular Weight: 203.284 Type of Substance: isocyclic InChI Key: ZAGBSZSITDFFAF-UHFFFAOYSA-N Note:

O

HN

Substance Label (2) Label References

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6b

Brunner, Henri; Kagan, Henri B.; Kreutzer, Georg; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2177 - 2187, View in Reaxys

XXI

Stevens et al.; Journal of the American Chemical Society; vol. 85; (1963); p. 1464,1466, View in Reaxys

Patent-Specific Data (1) Location in Patent References Claim

Patent; Preiss; Detlef; US5811464; (1998); (A) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.26

H Bond Donors

1

H Bond Acceptors

2

Rotatable Bonds

2

TPSA

29.1

Lipinski Number

4

Veber Number

2

Derivative (5) Comment (Derivative)

References

By formation of Brunner, Henri; Kagan, Henri B.; Kreutzer, Georg; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2177 - 2187, salt/complex; with View in Reaxys (R)-(-)-mandelic acid. Additional data: 1H NMR HCl-Salz: F: 255-256grad

Patent; Parke; Davis and Co.; US3254124; (1966); Chem.Abstr.; vol. 65; nb. 5414g; (1966), View in Reaxys

Hydrochlorid: C13H17NO*HCl: F: 256grad

Stevens et al.; Journal of the American Chemical Society; vol. 85; (1963); p. 1464,1466, View in Reaxys

Hydrochlorid: 1. Stevens et al.; Journal of the American Chemical Society; vol. 85; (1963); p. 1464,1466, View in Reaxys Bldg.: entspr. Oxim, wss. HCl <14h, Dampfbad>; Ausb. 82 percent; 2. Bldg.: <1-Methylamino-cyclopentyl>phenyl-keton, Δ <geschl. Rohr, 220grad, 10h>, Ausb. 20percent HCl-Salz: F: 255-257grad bzw. 256grad

Patent; Stevens; BE634208; (1962); Chem.Abstr.; vol. 61; nb. 5569c; (1964), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

256

Patent; Parke; Davis and Co.; US3254124; (1966); Chem.Abstr.; vol. 65; nb. 5414d; (1966), View in Reaxys Further Information (1) Description (FurReferences ther Information) Further information Stevens et al.; Journal of the American Chemical Society; vol. 85; (1963); p. 1464,1466, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

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Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 300.1 scopy) [MHz] Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications in Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys 2 of 4

Description (NMR Spectroscopy)

COSY (Correlation Spectroscopy); Spectrum

Nucleus (NMR Spectroscopy)

1H; 1H

Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications in Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys 3 of 4

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectro- 75.4 scopy) [MHz] Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications in Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys 4 of 4

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 300 scopy) [MHz] Brunner, Henri; Kagan, Henri B.; Kreutzer, Georg; Tetrahedron Asymmetry; vol. 14; nb. 15; (2003); p. 2177 - 2187, View in Reaxys Mass Spectrometry (4) Description (Mass References Spectrometry) electrospray ionisa- Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications tion (ESI); specin Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys trum electrospray ionisa- Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications tion (ESI); liquid in Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); spectrum electrospray ionisa- Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications tion (ESI); liquid in Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); CID (collision-in-

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duced dissociation); spectrum electron impact Frison, Giampietro; Zamengo, Luca; Zancanaro, Flavio; Tisato, Francesco; Traldi, Pietro; Rapid Communications (EI); gas chromain Mass Spectrometry; vol. 30; nb. 1; (2016); p. 151 - 160, View in Reaxys tography mass spectrometry (GCMS); fragmentation pattern; spectrum

Reaxys ID 2842448 View in Reaxys

3/4 CAS Registry Number: 7063-30-1 Chemical Name: 2-Methylamino-2-phenylcyclohexanon Linear Structure Formula: C13H17NO Molecular Formula: C13H17NO Molecular Weight: 203.284 Type of Substance: isocyclic InChI Key: ZAGBSZSITDFFAF-CYBMUJFWSA-N Note:

O

HN

Substance Label (1) Label References III

Stevens et al.; Journal of the American Chemical Society; vol. 88; (1966); p. 2769,2774, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.26

H Bond Donors

1

H Bond Acceptors

2

Rotatable Bonds

2

TPSA

29.1

Lipinski Number

4

Veber Number

2

Derivative (1) Comment (Derivative) Hydrochlorid: F: 256-258grad; F: 259-261grad; Therm. Umlagerung (Kinetik): Geschwindigkeitskonst.: ΔH(excit.), E(a); ΔS(excit.); ΔG(excit.)

References Stevens et al.; Journal of the American Chemical Society; vol. 88; (1966); p. 2769,2774, View in Reaxys

Reaxys ID 31731624 View in Reaxys

4/4 Chemical Name: S-2-(methylamino)-2-phenylcyclohexan-1-one hydrochloride Linear Structure Formula: C13H17NO*ClH Molecular Formula: C13H17NO*ClH Molecular Weight: 239.745 InChI Key: KJMDOBYGKOIRQI-ZOWNYOTGSA-N Note:

O HN H

Cl

Druglikeness (1)

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1 of 1

LogP

2.772

H Bond Donors

1

H Bond Acceptors

2

Rotatable Bonds

2

TPSA

29.1

Lipinski Number

4

Veber Number

2

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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