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Rimcazole

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Rimcazole
Clinical data
ATC code
  • none
Identifiers
  • 9-{3-[(3R,5S)-3,5-Dimethylpiperazin-1-yl]propyl}-9H-carbazole
CAS Number
PubChemCID
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 anantagonist[1] of thesigma receptor[2] as well as adopamine reuptake inhibitor.[3] Sigma receptors are thought to be involved in the drugpsychosis that can be induced by some drugs such asphencyclidine andcocaine, and rimcazole was originally researched as a potentialantipsychotic with a different mechanism of action to traditional antipsychotic drugs, although common withbutyrophenone antipsychotics such ashaloperidol. 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 theconvulsions caused by cocaineoverdose in animal models.[6]Isothiocyanatederivatives of rimcazole acting as irreversibledopamine transporter (DAT) blockers have been developed.[3]

See also

[edit]

References

[edit]
  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. ^abHusbands 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".J Med Chem.40 (26):4340–46.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.
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
σ1
σ2
Unsorted
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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