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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO2.C4H4O4
Molecular Weight 413.4636
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TREPIPAM MALEATE

SMILES

OC(=O)\C=C/C(O)=O.COC1=C(OC)C=C2[C@H](CN(C)CCC2=C1)C3=CC=CC=C3

InChI

InChIKey=TYNKKGLBKXZIHX-XLOMBBFOSA-N
InChI=1S/C19H23NO2.C4H4O4/c1-20-10-9-15-11-18(21-2)19(22-3)12-16(15)17(13-20)14-7-5-4-6-8-14;5-3(6)1-2-4(7)8/h4-8,11-12,17H,9-10,13H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t17-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C19H23NO2
Molecular Weight 297.3914
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Trepipam is a benzazepine derivative. It is a D1-dopamine antagonist. Trepipam significantly reduced aggression in behaviorally disturbed adolescents and in acute schizophrenics without producing concomitant sedation. Trepipam specifically reduces aggressive and hyperactive behaviors in a wide range of laboratory tests in various species, without producing signs of overt CNS depression or neurological impairment. The drug is effective in reducing many forms of aggression including brain stimulated emotional behavior. Trepipam actually had little effect on gross behavior in mice or rats and only produced ataxia at lethal doses.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
A clinical trial of a benzazepine (SCH 12679) in acute schizophrenic patients.
1972 Jun
The behavioral pharmacology of Sch 12679. A new psychoactive agent.
1974 May 15
[Pilot study of SCH-12679 in profoundly mentally retarded patients with severe behavior disorders].
1975 Jun
Effects of a novel anti-aggressive agent upon two types of brain stimulated emotional behavior.
1976 Jul 9
Effects of benzazepine (Sch-12679) on shock-induced fighting and locomotor behavior in rats.
1978 Oct 31
Gas-liquid chromatographic method for the measurement of plasma levels of d-7,8-dimethoxy-3-methyl-phenyl-2,3,4,5-tetrahydro-1h-3-benzazepine acid maleate (SCH-12679) and its major metabolites in aggressive mental retardites.
1979 May 1
Effects of the phenethylamine derivatives, BL-3912, fenfluramine, and Sch-12679, in rats trained with LSD as a discriminative stimulus.
1980
Prolactin releasing potencies of antipsychotic and related nonantipsychotic compounds in female rats: relation to clinical potencies.
1980 Aug
Comparison of SCH-12679 and thioridazine in aggressive mental retardates.
1980 Oct
Behavioural effects of psychoactive drugs on agonistic behaviour of male territorial rats (resident-intruder model).
1984
Evidence that lack of brain dopamine during development can increase the susceptibility for aggression and self-injurious behavior by influencing D1-dopamine receptor function.
1990
Pharmacological evaluation of SCH-12679: evidence for an in vivo antagonism of D1-dopamine receptors.
1990 Feb
Evidence for the involvement of dopamine in ambulation promoted by menthol in mice.
2003 Feb
Endogenous dopamine maintains synchronous oscillation of intracellular calcium in primary cultured-mouse midbrain neurons.
2004 Feb
Evidence for dopamine involvement in ambulation promoted by menthone in mice.
2009 Jan
Evidence for dopamine involvement in ambulation promoted by pulegone in mice.
2010 Feb
Patents

Patents

Substance Class Chemical
Created
by admin
on Tue Oct 22 05:57:29 UTC 2019
Edited
by admin
on Tue Oct 22 05:57:29 UTC 2019
Record UNII
D6074YC6T3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TREPIPAM MALEATE
USAN  
USAN  
Official Name English
1H-3-BENZAZEPINE, 2,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-3-METHYL-1-PHENYL-, (+)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
1H-3-BENZAZEPINE, 2,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-3-METHYL-1-PHENYL-, (1R)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
SCH 12679
Code English
TREPIPAM MALEATE [USAN]
Common Name English
TRIMONAM MALEATE
Common Name English
SCH-12679
Code English
TRIMOPAM MALEATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL343569
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
PRIMARY
PUBCHEM
6434250
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
PRIMARY
ECHA (EC/EINECS)
254-546-1
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
PRIMARY
CAS
39624-66-3
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
PRIMARY
NCI_THESAURUS
C152729
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
PRIMARY
EPA CompTox
39624-66-3
Created by admin on Tue Oct 22 05:57:29 UTC 2019 , Edited by admin on Tue Oct 22 05:57:29 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY