Rimcazole

Rimcazole

Systematic (IUPAC) name
9-{3-[(3R,5S)-3,5-Dimethylpiperazin-1-yl]propyl}-9H-carbazole
Identifiers
CAS Number	75859-04-0
ATC code	none
PubChem	CID 53389
ChemSpider	48221
UNII	C3N1PS8CX1
ChEMBL	CHEMBL275707
Chemical data
Formula	C21H27N3
Molar mass	321.459
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+ Key:GUDVQJXODNJRIJ-CALCHBBNSA-N
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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

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.
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.