Query Query
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Date
2 substances in Reaxys
2018-03-25 13h:29m:07s (EST)
O
1. Query
N
Search as: As drawn
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Reaxys ID 1252117 View in Reaxys
1/2 CAS Registry Number: 2201-35-6 Chemical Name: 1-[1-(4-methoxy-phenyl)-cyclohexyl]-piperidine; 1-<1-(4-Methoxy-phenyl)-cyclohexyl>-piperidin Linear Structure Formula: C18H27NO Molecular Formula: C18H27NO Molecular Weight: 273.418 Type of Substance: heterocyclic InChI Key: MUZGGFNYVLGUFS-UHFFFAOYSA-N Note:
O N
Substance Label (3) Label References 11 (methylated p-5)
Masumoto; Takeuchi; Ohta; Hirobe; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 7; (1989); p. 1788 1794, View in Reaxys
GK 27
Geneste et al.; European Journal of Medicinal Chemistry; vol. 14; (1979); p. 301,302, View in Reaxys
VI
Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys
Druglikeness (1) 1 of 1
LogP
4.133
H Bond Donors
0
H Bond Acceptors
1
Rotatable Bonds
3
TPSA
12.47
Lipinski Number
4
Veber Number
2
Derivative (2) Comment (Derivative)
References
*HCl: F: 171-172grad (korr.); pK(a)
Geneste et al.; European Journal of Medicinal Chemistry; vol. 14; (1979); p. 301,302, View in Reaxys
Hydrochlorid C18H27NO*HCl: F:186-187grad (unkorr.)
MADDOX; GODEFROI; PARCELL; Journal of medicinal chemistry; vol. 8; (1965); p. 230 - 235, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
50 - 51
Geneste et al.; European Journal of Medicinal Chemistry; vol. 14; (1979); p. 301,302, View in Reaxys Dissociation Exponent (1) 1 of 1
Comment (Dissociation Exponent)
(pk')pk(a)
Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys Further Information (1) Description (Fur- References ther Information) Further information
MADDOX; GODEFROI; PARCELL; Journal of medicinal chemistry; vol. 8; (1965); p. 230 - 235, View in Reaxys
Liquid/Liquid Systems (MCS) (1) 1 of 1
Description (Liquid/ Liquid Systems (MCS))
Distribution between solvent 1 + 2
Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry)
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spectrum; electron impact (EI)
Masumoto; Takeuchi; Ohta; Hirobe; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 7; (1989); p. 1788 1794, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
UV/VIS
Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys Medchem (5) 1 of 5
Bioassay Category
In Vivo (Animal models)
Bioassay Name
Rotarod test
Biological Species/NCBI Swiss Webster mouse ID Substance RN
1252117View in Reaxys
Substance Name
GK27
Substance Route of Adm.
subcutaneous administration
Substance Dosing Regi- Single men Measurement Parameter
ED50
Unit
mg/kg
Quantitative value
20
Geneste; Kamenka; Ung; et al.; European Journal of Medicinal Chemistry; vol. 14; nb. 4; (1979); p. 301 - 308, View in Reaxys 2 of 5
Target Name
Glutamate receptor ionotropic, NMDA 2A [human];+Glutamate receptor ionotropic, NMDA 1 [human]
Target Synonyms
glun2a; glutamate; glutamate receptor ionotropic, nmda 2a; grin2a; hnr2a; n-methyl d-aspartate receptor subtype 2a; nmdar2a; nr2a + glun1; glutamate; glutamate receptor ionotropic, nmda 1; grin1 (glutamate receptor ionotropic, nmda 1); n-methyl-d-aspartate receptor subunit nr1; nmd-r1; nmdar1
Target Uniprot ID
q12879 + q05586
Target PDB ID
3nfl + 2hqw; 3bya
Target, Subunit, Species Glutamate receptor ionotropic, NMDA 1 [human]; Glutamate receptor ionotropic, NMDA 2A [human] Target Mutant/Chimera Details
Glutamate receptor ionotropic, NMDA 2A [human]:Wild + Glutamate receptor ionotropic, NMDA 1 [human]:Wild
Target Species (Bioactivity)
human
Target Transfection
Transfected
Substance Action on Target
Antagonist
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Flux uptake
Cells/Cell Lines
U-2 OS
Substance RN
1252117View in Reaxys
Substance Name
Cpd 1
Measurement Parameter
pIC50
Quantitative value
4.8
Deviation
0.270000
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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3 of 5
Measurement pX
4.8
Concomitants: Compound RN
4241647
Concomitants: Compound name
Ca2+
Concomitants: Compound role
SUB
Target Name
Glutamate receptor ionotropic, NMDA 2B [human];+Glutamate receptor ionotropic, NMDA 1 [human]
Target Synonyms
glun2b; glutamate; glutamate receptor ionotropic, nmda 2b; grin2b; hnr3; n-methyl d-aspartate receptor subtype 2b; n-methyl-d-aspartate receptor subunit 3; nmdar2b; nr2b; nr3 + glun1; glutamate; glutamate receptor ionotropic, nmda 1; grin1 (glutamate receptor ionotropic, nmda 1); n-methyl-d-aspartate receptor subunit nr1; nmd-r1; nmdar1
Target Uniprot ID
q13224 + q05586
Target PDB ID
2hqw; 3bya
Target, Subunit, Species Glutamate receptor ionotropic, NMDA 1 [human]; Glutamate receptor ionotropic, NMDA 2B [human]
4 of 5
Target Mutant/Chimera Details
Glutamate receptor ionotropic, NMDA 2B [human]:Wild + Glutamate receptor ionotropic, NMDA 1 [human]:Wild
Target Species (Bioactivity)
human
Target Transfection
Transfected
Substance Action on Target
Antagonist
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Flux uptake
Cells/Cell Lines
U-2 OS
Substance RN
1252117View in Reaxys
Substance Name
Cpd 1
Measurement Parameter
pIC50
Quantitative value
5.4
Deviation
0.270000
Measurement pX
5.4
Concomitants: Compound RN
4241647
Concomitants: Compound name
Ca2+
Concomitants: Compound role
SUB
Target Name
Glutamate receptor ionotropic, NMDA 2A [human];+Glutamate receptor ionotropic, NMDA 1 [human]
Target Synonyms
glun2a; glutamate; glutamate receptor ionotropic, nmda 2a; grin2a; hnr2a; n-methyl d-aspartate receptor subtype 2a; nmdar2a; nr2a + glun1; glutamate; glutamate receptor ionotropic, nmda 1; grin1 (glutamate receptor ionotropic, nmda 1); n-methyl-d-aspartate receptor subunit nr1; nmd-r1; nmdar1
Target Uniprot ID
q12879 + q05586
Target PDB ID
3nfl + 2hqw; 3bya
Target, Subunit, Species Glutamate receptor ionotropic, NMDA 1 [human]; Glutamate receptor ionotropic, NMDA 2A [human]
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5 of 5
Target Mutant/Chimera Details
Glutamate receptor ionotropic, NMDA 2A [human]:Wild + Glutamate receptor ionotropic, NMDA 1 [human]:Wild
Target Species (Bioactivity)
human
Target Transfection
Transfected
Substance Action on Target
Antagonist
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Flux uptake
Cells/Cell Lines
U-2 OS
Substance RN
1252117View in Reaxys
Substance Name
Cpd 1
Measurement Parameter
Emax(%)
Unit
%
Quantitative value
94 - 100
Concomitants: Compound RN
4241647
Concomitants: Compound name
Ca2+
Concomitants: Compound role
SUB
Target Name
Glutamate receptor ionotropic, NMDA 2B [human];+Glutamate receptor ionotropic, NMDA 1 [human]
Target Synonyms
glun2b; glutamate; glutamate receptor ionotropic, nmda 2b; grin2b; hnr3; n-methyl d-aspartate receptor subtype 2b; n-methyl-d-aspartate receptor subunit 3; nmdar2b; nr2b; nr3 + glun1; glutamate; glutamate receptor ionotropic, nmda 1; grin1 (glutamate receptor ionotropic, nmda 1); n-methyl-d-aspartate receptor subunit nr1; nmd-r1; nmdar1
Target Uniprot ID
q13224 + q05586
Target PDB ID
2hqw; 3bya
Target, Subunit, Species Glutamate receptor ionotropic, NMDA 1 [human]; Glutamate receptor ionotropic, NMDA 2B [human] Target Mutant/Chimera Details
Glutamate receptor ionotropic, NMDA 2B [human]:Wild + Glutamate receptor ionotropic, NMDA 1 [human]:Wild
Target Species (Bioactivity)
human
Target Transfection
Transfected
Substance Action on Target
Antagonist
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Flux uptake
Cells/Cell Lines
U-2 OS
Substance RN
1252117View in Reaxys
Substance Name
Cpd 1
Measurement Parameter
Emax(%)
Unit
%
Quantitative value
94 - 100
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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Concomitants: Compound RN
4241647
Concomitants: Compound name
Ca2+
Concomitants: Compound role
SUB
Reaxys ID 4606236 View in Reaxys Cl
2/2 CAS Registry Number: 2185-93-5 Linear Structure Formula: C18H27NO*ClH Molecular Formula: C18H27NO*ClH Molecular Weight: 309.879 Type of Substance: heterocyclic InChI Key: FYAFJNVLHWQLHK-UHFFFAOYSA-N Note:
H
O N
Substance Label (1) Label References 3a
Brine; Boldt; Coleman; Carroll; Journal of Heterocyclic Chemistry; vol. 21; nb. 1; (1984); p. 71 - 75, View in Reaxys
Druglikeness (1) 1 of 1
LogP
4.645
H Bond Donors
0
H Bond Acceptors
1
Rotatable Bonds
3
TPSA
12.47
Lipinski Number
4
Veber Number
2
Melting Point (1) 1 of 1
Melting Point [°C]
177 - 178.5
Comment (Melting Point)
Details: new mp after resolidification at: 230 C - 232 C
Brine; Boldt; Coleman; Carroll; Journal of Heterocyclic Chemistry; vol. 21; nb. 1; (1984); p. 71 - 75, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Brine; Boldt; Coleman; Carroll; Journal of Heterocyclic Chemistry; vol. 21; nb. 1; (1984); p. 71 - 75, View in Reaxys Medchem (8) 1 of 8
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Digging activity of the compound was determined as number of gerbils out of 4 which did not pass sand barrier after 30 min at a dose of 10 mg\kg
Biological Species/NCBI gerbil ID Substance RN
4606236View in Reaxys
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Measurement Parameter
Number
Measurement Object
Number of animals
Quantitative value
2
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 2 of 8
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Percent reduction in performance of forced motor activity in mice after 30 min at a dose of 10 mg\kg
Biological Species/NCBI Mus musculus ID Substance RN
4606236View in Reaxys
Measurement Parameter
%
Unit
%
Measurement Object
Reduction activity
Qualitative value
=
Quantitative value
0
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 3 of 8
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Digging activity of the compound was determined as number of gerbils out of 4 which did not pass sand barrier after 60 min at a dose of 10 mg\kg
Biological Species/NCBI gerbil ID Substance RN
4606236View in Reaxys
Measurement Parameter
Number
Measurement Object
Number of animals
Quantitative value
2
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 4 of 8
Bioassay Category
In Vivo (Animal models)
Bioassay Details
Tested for main behavioral changes of cats at a intraventricular dose of 200 microg; None
Biological Species/NCBI domestic cat ID Substance RN
4606236View in Reaxys
Measurement Parameter
Qualitative
Measurement Object
Main behavioral changes
Qualitative value
Not Published
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 5 of 8
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Percent reduction in performance of forced motor activity in mice after 60 min at a dose of 10 mg\kg
Biological Species/NCBI Mus musculus ID
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Substance RN
4606236View in Reaxys
Measurement Parameter
%
Unit
%
Measurement Object
Reduction activity
Qualitative value
=
Quantitative value
0
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 6 of 8
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Digging activity of the compound was determined as number of gerbils out of 4 which did not pass sand barrier after 60 min at a dose of 5 mg\kg
Biological Species/NCBI gerbil ID Substance RN
4606236View in Reaxys
Measurement Parameter
Number
Measurement Object
Number of animals
Quantitative value
0
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 7 of 8
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Percent reduction in response of conditioned avoidance response (CAR) in rats at a dose of 10 mg\kg
Biological Species/NCBI Rattus norvegicus ID Substance RN
4606236View in Reaxys
Measurement Parameter
%
Unit
%
Measurement Object
Reduction activity
Qualitative value
=
Quantitative value
0
Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys 8 of 8
Bioassay Category
In Vivo (Animal models)
Bioassay Details
Compound was tested for cataleptic activity by measuring loss of righting reflex without head drop in pigeon upon intramuscular injection at the dose of 6-25 mg/kg; active members exhibiting maximum activity at the above mentioned dose
Biological Species/NCBI pigeon ID Substance RN
4606236View in Reaxys
Substance Route of Adm.
intramuscular administration
Measurement Parameter
Activity
Measurement Object
Cataleptic activity by measuring loss of righting reflex without head drop in pigeon
Qualitative value
ND
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MADDOX; GODEFROI; PARCELL; Journal of medicinal chemistry; vol. 8; (1965); p. 230 - 235, View in Reaxys
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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