TREPIPAM

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ICPHJSKVAZMKIV-QGZVFWFLSA-N

InChI=1S/C19H23NO2/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/h4-8,11-12,17H,9-10,13H2,1-3H3/t17-/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9658 | https://www.ncbi.nlm.nih.gov/pubmed/7417923 | https://www.ncbi.nlm.nih.gov/pubmed/1982973 | https://www.ncbi.nlm.nih.gov/pubmed/4211174

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

Title	Date	PubMed
A clinical trial of a benzazepine (SCH 12679) in acute schizophrenic patients.	1972 Jun	4625801
Effects of a novel anti-aggressive agent upon two types of brain stimulated emotional behavior.	1976 Jul 9	9658
Effects of benzazepine (Sch-12679) on shock-induced fighting and locomotor behavior in rats.	1978 Oct 31	103121
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	528626
Effects of the phenethylamine derivatives, BL-3912, fenfluramine, and Sch-12679, in rats trained with LSD as a discriminative stimulus.	1980	6776559
Prolactin releasing potencies of antipsychotic and related nonantipsychotic compounds in female rats: relation to clinical potencies.	1980 Aug	6104725
Comparison of SCH-12679 and thioridazine in aggressive mental retardates.	1980 Oct	7417923
Behavioural effects of psychoactive drugs on agonistic behaviour of male territorial rats (resident-intruder model).	1984	6095317
Endogenous dopamine maintains synchronous oscillation of intracellular calcium in primary cultured-mouse midbrain neurons.	2004 Feb	15049510
Evidence for dopamine involvement in ambulation promoted by menthone in mice.	2009 Jan	18718482
Evidence for dopamine involvement in ambulation promoted by pulegone in mice.	2010 Feb	19917306

Patents

Name

Type

Language

TREPIPAM

Official Name

English

trepipam [INN]

Common Name

English

1H-3-BENZAZEPINE, 2,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-3-METHYL-1-PHENYL-, (1R)-

Systematic Name

English

TRIMOPAM

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884