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
IUPAC name
  • 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)
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)

References
  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. Eaton MJ, Lookingland KJ, Moore KE (1996). "The sigma ligand rimcazole activates noradrenergic neurons projecting to the paraventricular nucleus and increases corticosterone secretion in rats". Brain Res. 733 (2): 162–6. doi:10.1016/0006-8993(96)00290-9. PMID 8891298. S2CID 42885767.
  3. Husbands, S. M.; Izenwasser, S; Loeloff, R. J.; Katz, J. L.; Bowen, W. D.; Vilner, B. J.; Newman, A. H. (1997). "Isothiocyanate derivatives of 9-3-(cis-3,5-dimethyl-1-piperazinyl)propylcarbazole (rimcazole): Irreversible ligands for the dopamine transporter". Journal of Medicinal Chemistry. 40 (26): 4340–46. doi:10.1021/jm9705519. PMID 9435903.
  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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