Piquindone

Piquindone (Ro 22-1319) is an atypical antipsychotic with a tricyclic structure that was developed in the 1980s but was never marketed.^[1][2][3] It acts as a selective D₂ receptor antagonist,^[4][5][6] though based on its effects profile its selectivity may be considered controversial. Unlike most other D₂ receptor ligands, piquindone displays Na⁺-dependent binding, a property it shares with tropapride, zetidoline, and metoclopramide.^[7]

Routes of
administrationOral

ATC code

• none

Legal status

• In general: uncontrolled

CAS Number

• 78541-97-6
  83784-19-4 (hydrochloride)

Quick facts Clinical data, Routes ofadministration ...

Piquindone

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
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
CAS Number	78541-97-6 83784-19-4 (hydrochloride)
PubChem CID	121903
ChemSpider	108751
UNII	O1C9WXY65C
ChEMBL	ChEMBL1192678
CompTox Dashboard (EPA)	DTXSID701016495
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2c1c([nH]c(c1CC)C)C[C@H]3[C@H]2CN(CC3)C

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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.^[1] 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.^[1][3] In addition to psychosis, piquindone has also been found to be effective in the treatment of Tourette's syndrome in numerous clinical studies.^{[8][9][10][11]}