Rimcazole

Chemical compound From Wikipedia, the free encyclopedia

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, although common with butyrophenone antipsychotics such as haloperidol. 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]

ATC code
  • none
CAS Number
PubChem CID
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Rimcazole
Clinical data
ATC code
  • none
Identifiers
  • 9-{3-[(3R,5S)-3,5-Dimethylpiperazin-1-yl]propyl}-9H-carbazole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H27N3
Molar mass321.468 g·mol−1
3D model (JSmol)
  • C[C@@H]1CN(C[C@@H](N1)C)CCCN2C3=CC=CC=C3C4=CC=CC=C42
  • 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
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