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]

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 mass321.459 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
 ☒NcheckY (what is this?)  (verify)

References
  1. Gilmore DL, Liu Y, Matsumoto RR (2004). "Review of the pharmacological and clinical profile of rimcazole". CNS Drug Reviews. 10 (1): 1–22. doi:10.1111/j.1527-3458.2004.tb00001.x. PMC 6741722. PMID 14978511.
  2. Eaton MJ, Lookingland KJ, Moore KE (September 1996). "The sigma ligand rimcazole activates noradrenergic neurons projecting to the paraventricular nucleus and increases corticosterone secretion in rats". Brain Research. 733 (2): 162–166. doi:10.1016/0006-8993(96)00290-9. PMID 8891298. S2CID 42885767.
  3. Husbands SM, Izenwasser S, Loeloff RJ, Katz JL, Bowen WD, Vilner BJ, Newman AH (December 1997). "Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole): irreversible ligands for the dopamine transporter". Journal of Medicinal Chemistry. 40 (26): 4340–4346. doi:10.1021/jm9705519. PMID 9435903.
  4. Volz HP, Stoll KD (November 2004). "Clinical trials with sigma ligands". Pharmacopsychiatry. 37 Suppl 3: S214–S220. doi:10.1055/s-2004-832680. PMID 15547788. S2CID 260238757.
  5. Katz JL, Libby TA, Kopajtic T, Husbands SM, Newman AH (May 2003). "Behavioral effects of rimcazole analogues alone and in combination with cocaine". European Journal of Pharmacology. 468 (2): 109–119. doi:10.1016/s0014-2999(03)01638-8. PMID 12742518.
  6. Matsumoto RR, Hewett KL, Pouw B, Bowen WD, Husbands SM, Cao JJ, Newman AH (December 2001). "Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters". Neuropharmacology. 41 (7): 878–886. doi:10.1016/s0028-3908(01)00116-2. PMID 11684152. S2CID 44328858.
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