Ciclindole

Ciclindole
Clinical data
Other namesWIN-27,147-2; WIN-27147-2; WIN27147-2
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H18N2
Molar mass214.312 g·mol−1
3D model (JSmol)
  • c21c(cccc1)[nH]c3c2CC(N(C)C)CC3

Ciclindole (INNTooltip International Nonproprietary Name; developmental code name WIN-27,147-2), also known as cyclindole (USANTooltip United States Adopted Name), is an antipsychotic of the tetrahydrocarbazolamine family with a tricyclic cyclized tryptamine structure that was never marketed.

It displaces spiperone binding in vitro and elevates dopamine levels in the striatum, indicating that it acts as a dopamine D2 receptor antagonist. It also shows apparent affinity for the α1-adrenergic receptor, the serotonin S1 receptor, and the serotonin S2 receptor. However, its affinities for all of the preceding targets are weak, in the low micromolar range.

The related drug flucindole is about 5 to 10 times more potent than ciclindole both in vitro and in vivo.

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