Rimcazole

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Rimcazole
Rimcazole.svg
Systematic (IUPAC) name
9-{3-[(3R,5S)-3,5-Dimethylpiperazin-1-yl]propyl}-9H-carbazole
Identifiers
CAS Number 75859-04-0 YesY
ATC code none
PubChem CID: 53389
ChemSpider 48221 N
UNII C3N1PS8CX1 N
ChEMBL CHEMBL275707 N
Chemical data
Formula C21H27N3
Molecular mass 321.459
  • 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
 NYesY (what is this?)  (verify)

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]

References

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  1. ↑ Gilmore DL, Liu Y, Matsumoto RR. Review of the pharmacological and clinical profile of rimcazole. CNS Drug Reviews. 2004 Spring;10(1):1-22.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Volz HP, Stoll KD. Clinical trials with sigma ligands. Pharmacopsychiatry. 2004 Nov;37 Suppl 3:S214-20.
  5. ↑ Katz JL, Libby TA, Kopajtic T, Husbands SM, Newman AH. Behavioral effects of rimcazole analogues alone and in combination with cocaine. European Journal of Pharmacology. 2003 May 9;468(2):109-19.
  6. ↑ Matsumoto RR, Hewett KL, Pouw B, Bowen WD, Husbands SM, Cao JJ, Hauck Newman A. Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters. Neuropharmacology. 2001 Dec;41(7):878-86.
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