Piquindone

Piquindone

Systematic (IUPAC) name
(4aS,8aS)-3-ethyl-2,6-dimethyl-1,4a,5,6,7,8,8a,9-octahydro-4H-pyrrolo[2,3-g]isoquinolin-4-one
Clinical data
Legal status	Uncontrolled
Routes of administration	Oral
Identifiers
CAS Number	78541-97-6 83784-19-4 (hydrochloride)
ATC code	none
PubChem	CID: 121903
ChemSpider	108751
UNII	O1C9WXY65C Y
ChEMBL	CHEMBL1192678
Chemical data
Formula	C15H22N2O
Molecular mass	246.35 g/mol
SMILES O=C2c1c(nc(c1CC)C)C[C@H]3[C@H]2CN(CC3)C

Piquindone (Ro 22-1319) is an atypical antipsychotic with a tricyclic structure that was developed in the 1980s but was never marketed. It acts as a selective D₂ receptor antagonist, though based on its effects profile its selectivity may be considered controversial. Unlike most other D₂ receptor ligands, piquindone displays Na²⁺-dependent binding, a property it shares with tropapride, zetidoline, and metoclopramide.

In clinical trials piquindone was found to possess moderate efficacy in treating positive symptoms of schizophrenia, and notably, was also modestly effective for negative symptoms, though this was just under statistical significance. Additionally, relative to haloperidol, it was found to possesses significantly fewer extrapyramidal symptoms and had a much lower propensity for inducing tardive dyskinesia, indicating its atypical nature. In addition to psychosis, piquindone has also been found to be effective in the treatment of Tourette's syndrome in numerous clinical studies.

See also

• Losindole
• Molindone