Rimcazole

Overview

Rimcazole is an antagonist of the sigma receptor as well as a dopamine reuptake inhibitor. 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, although common with butyrophenone antipsychotics such as haloperidol. 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. Rimcazole has been shown to reduce the effects of cocaine, and analogues of rimcazole have been shown to be highly effective at blocking the convulsions caused by cocaine overdose in animal models. Isothiocyanate derivatives of rimcazole acting as irreversible dopamine transporter (DAT) blockers have been developed.[1–6] WP

Chemistry

Formula

C21H27N3 PC

CAS number

75859-04-0 PC

Molar mass (g/mol)

321.5 PC

IUPAC name (computed by PubChem)

9-[3-[(3R,5S)-3,5-dimethylpiperazin-1-yl]propyl]carbazole PC

SMILES

C[C@@H]1CN(C[C@@H](N1)C)CCCN2C3=CC=CC=C3C4=CC=CC=C42 PC

InChIKey

GUDVQJXODNJRIJ-CALCHBBNSA-N PC

PubChem CID

53389

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Gilmore DL, Liu Y, Matsumoto RR. Review of the pharmacological and clinical profile of rimcazole. CNS Drug Reviews. 2004. doi:10.1111/j.1527-3458.2004.tb00001.x · PMID 14978511 · PMC6741722
2. Journal / agency Eaton MJ, Lookingland KJ, Moore KE. The sigma ligand rimcazole activates noradrenergic neurons projecting to the paraventricular nucleus and increases corticosterone secretion in rats. Brain Research. September 1996. doi:10.1016/0006-8993(96)00290-9 · PMID 8891298
3. Journal / agency Husbands SM, Izenwasser S, Loeloff RJ, Katz JL, Bowen WD, Vilner BJ, Newman AH. Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole): irreversible ligands for the dopamine transporter. J Med Chem. December 1997. doi:10.1021/jm9705519 · PMID 9435903
4. Journal / agency Volz HP, Stoll KD. Clinical trials with sigma ligands. Pharmacopsychiatry. November 2004. doi:10.1055/s-2004-832680 · PMID 15547788
5. Journal / agency 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. May 2003. doi:10.1016/s0014-2999(03)01638-8 · PMID 12742518
6. Journal / agency Matsumoto RR, Hewett KL, Pouw B, Bowen WD, Husbands SM, Cao JJ, Newman AH. Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters. Neuropharmacology. December 2001. doi:10.1016/s0028-3908(01)00116-2 · PMID 11684152

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.