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Rimcazole

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 mass321.468 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)

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 (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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