TREPIPAM MALEATE

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 Search

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	No
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	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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
Evidence for dopamine involvement in ambulation promoted by pulegone in mice.	2010-02	19917306
Evidence for dopamine involvement in ambulation promoted by menthone in mice.	2009-01	18718482
Endogenous dopamine maintains synchronous oscillation of intracellular calcium in primary cultured-mouse midbrain neurons.	2004-02	15049510
Evidence for the involvement of dopamine in ambulation promoted by menthol in mice.	2003-02	12686756
Pharmacological evaluation of SCH-12679: evidence for an in vivo antagonism of D1-dopamine receptors.	1990-02	1968972
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	1982973
Behavioural effects of psychoactive drugs on agonistic behaviour of male territorial rats (resident-intruder model).	1984	6095317
Comparison of SCH-12679 and thioridazine in aggressive mental retardates.	1980-10	7417923
Prolactin releasing potencies of antipsychotic and related nonantipsychotic compounds in female rats: relation to clinical potencies.	1980-08	6104725
Effects of the phenethylamine derivatives, BL-3912, fenfluramine, and Sch-12679, in rats trained with LSD as a discriminative stimulus.	1980	6776559
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.	1979-05-01	528626
Effects of benzazepine (Sch-12679) on shock-induced fighting and locomotor behavior in rats.	1978-10-31	103121
Effects of a novel anti-aggressive agent upon two types of brain stimulated emotional behavior.	1976-07-09	9658
[Pilot study of SCH-12679 in profoundly mentally retarded patients with severe behavior disorders].	1975-06	4912
The behavioral pharmacology of Sch 12679. A new psychoactive agent.	1974-05-15	4211174
A clinical trial of a benzazepine (SCH 12679) in acute schizophrenic patients.	1972-06	4625801

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:52:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:01 GMT 2025`
Record UNII	D6074YC6T3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCH 12679

Preferred Name

English

TREPIPAM MALEATE

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

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