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Ciclindole
Clinical data
Other names	WIN-27,147-2; WIN-27147-2; WIN27147-2
Routes of; administration	Oral
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine;
CAS Number	32211-97-5;
PubChem CID	36082;
ChemSpider	33189;
UNII	CXJ7G6BYD7;
KEGG	D03619;
ChEMBL	ChEMBL2104160;
CompTox Dashboard (EPA)	DTXSID10865627 ;
Chemical and physical data
Formula	C14H18N2
Molar mass	214.312 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 with a tricyclic and tryptamine-like structure that was never marketed.^[1]^[2]

It displaces spiperone binding in vitro and elevates dopamine levels in the striatum, indicating that it acts as a dopamine D₂ receptor antagonist.^[2] It also shows apparent affinity for the α₁-adrenergic receptor, the serotonin S₁ receptor, and the serotonin S₂ receptor.^[2] However, its affinities for all of the preceding targets are weak, in the low micromolar range.^[2]

The related drug flucindole is about 5 to 10 times more potent than ciclindole both in vitro and in vivo.^[2]

References

^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
^ ^a ^b ^c ^d ^e Wood PL, McQuade PS (1984). "Ciclindole and flucindole: novel tetrahydrocarbazolamine neuroleptics". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 8 (4–6): 773–7. doi:10.1016/0278-5846(84)90057-5. PMID 6152347. S2CID 39252411.