RIMCAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27N3
Molecular Weight	321.4592
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1CN(CCCN2C3=C(C=CC=C3)C4=C2C=CC=C4)C[C@@H](C)N1

InChI

InChIKey=GUDVQJXODNJRIJ-CALCHBBNSA-N

InChI=1S/C21H27N3/c1-16-14-23(15-17(2)22-16)12-7-13-24-20-10-5-3-8-18(20)19-9-4-6-11-21(19)24/h3-6,8-11,16-17,22H,7,12-15H2,1-2H3/t16-,17+

HIDE SMILES / InChI

Molecular Formula	C21H27N3
Molecular Weight	321.4592
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14978511 | https://www.ncbi.nlm.nih.gov/pubmed/12210554 | https://www.ncbi.nlm.nih.gov/pubmed/9826105 | https://www.ncbi.nlm.nih.gov/pubmed/1681560

Rimcazole is a carbazole derivative that acts as a sigma receptor antagonist and studied as potential antipsychotic agent for the treatment of acute schizophrenic patients. In open-clinical trials Rimcazole (BW 234U) appears to be effective in acute schizophrenic patients. However, subsequent clinical trials demonstrated that rimcazole lacked efficacy in schizophrenic patients and it is now primarily used as an experimental tool. In addition to its actions as  receptor antagonist, rimcazole also has high affinity for dopamine transporters, and inrecent years it has served as a lead compound for the development of novel dopamine transporter ligands.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sigma opioid receptor 64 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2873494	Antagonist 2849
Dopamine transporter 183 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435903	Binding Agent 1076

PubMed

Title	Date	PubMed
Discovery of highly potent small molecule Hepatitis C Virus entry inhibitors.	2011-11-15	21978675
The role of RelA (p65) threonine 505 phosphorylation in the regulation of cell growth, survival, and migration.	2011-09	21737676
Review of the pharmacological and clinical profile of rimcazole.	2004	14978511
Dual probes for the dopamine transporter and sigma1 receptors: novel piperazinyl alkyl-bis(4'-fluorophenyl)amine analogues as potential cocaine-abuse therapeutic agents.	2003-06-19	12801223
Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters.	2001-12	11684152
Effect of sigma ligands on the cocaine-induced convulsions in mice.	2000-05-19	10817525
Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole): irreversible ligands for the dopamine transporter.	1997-12-19	9435903
Neuropharmacological profile of EMD 57445, a sigma receptor ligand with potential antipsychotic activity.	1996-11-21	8982660

Patents

Sample Use Guides

In Vivo Use Guide

5 mg/kg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:21:11 GMT 2025` Edited by `admin` on `Wed Apr 02 08:21:11 GMT 2025`
Record UNII	C3N1PS8CX1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BW 234U

Preferred Name

English

RIMCAZOLE

Official Name

English

9H-CARBAZOLE, 9-(3-((3R,5S)-3,5-DIMETHYL-1-PIPERAZINYL)PROPYL)-, REL-

Common Name

English

9-(3-(CIS-3,5-DIMETHYL-1-PIPERAZINYL)PROPYL)CARBAZOLE

Systematic Name

English

BW-234U

Code

English

rimcazole [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710