Rimcazole

Rimcazole

Systematic (IUPAC) name
9-{3-[(3R,5S)-3,5-dimethylpiperazin-1-yl]propyl}-9H-carbazole
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	75859-04-0 Y
ATC code	None
PubChem	CID 53389
UNII	C3N1PS8CX1 N
ChEMBL	CHEMBL275707 N
Chemical data
Formula	C21H27N3
Mol. mass	321.459
N (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 PCP 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 et al (1997) Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]-carbazole (Rimcazole): irreversible ligands for the dopamine transporter. J.Med.Chem. 40 4340. 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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