Rimcazole

Rimcazole is an antagonist^[1] of the sigma receptor^[2] as well as a dopamine reuptake inhibitor.^[3] Sigma receptors are thought to be involved in the drug psychosis that can be induced by some drugs such as phencyclidine and cocaine, and rimcazole was originally researched as a potential antipsychotic with a different mechanism of action to traditional antipsychotic drugs. Trials proved inconclusive and rimcazole was not pursued for this application, but other sigma antagonists continue to be researched for a variety of potential applications.^[4] Rimcazole has been shown to reduce the effects of cocaine,^[5] and analogues of rimcazole have been shown to be highly effective at blocking the convulsions caused by cocaine overdose in animal models.^[6] Isothiocyanate derivatives of rimcazole acting as irreversible dopamine transporter (DAT) blockers have been developed.^[3]

Rimcazole

Clinical data
ATC code	none
Identifiers
IUPAC name 9-{3-[(3R,5S)-3,5-Dimethylpiperazin-1-yl]propyl}-9H-carbazole
CAS Number	75859-04-0 Y
PubChem CID	53389
ChemSpider	48221 N
UNII	C3N1PS8CX1
ChEMBL	ChEMBL275707 N
CompTox Dashboard (EPA)	DTXSID7048162
Chemical and physical data
Formula	C21H27N3
Molar mass	321.468 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@@H]1CN(C[C@@H](N1)C)CCCN2C3=CC=CC=C3C4=CC=CC=C42
InChI 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+ N Key:GUDVQJXODNJRIJ-CALCHBBNSA-N N
NY (what is this?)  (verify)

See also

• Amineptine