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 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2873494	Antagonist 2778
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435903	Binding Agent 1064

PubMed

Title	Date	PubMed
Neuropharmacological profile of EMD 57445, a sigma receptor ligand with potential antipsychotic activity.	1996 Nov 21	8982660
Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole): irreversible ligands for the dopamine transporter.	1997 Dec 19	9435903
Effect of sigma ligands on the cocaine-induced convulsions in mice.	1999 Nov-Dec	10817525
Discovery of highly potent small molecule Hepatitis C Virus entry inhibitors.	2011 Nov 15	21978675

Patents

Sample Use Guides

In Vivo Use Guide

5 mg/kg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:45:36 UTC 2023` Edited by `admin` on `Sat Dec 16 16:45:36 UTC 2023`
Record UNII	C3N1PS8CX1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIMCAZOLE

Official Name

English

BW 234U

Code

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