Ciclindole

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.^[1][2]

Other namesWIN-27,147-2; WIN-27147-2; WIN27147-2

Routes of
administrationOral

ATC code

• None

Legal status

• In general: uncontrolled

Quick facts Clinical data, Other names ...

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

Close

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]