PIQUINDONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H22N2O
Molecular Weight	246.348
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C(C)NC2=C1C(=O)[C@@H]3CN(C)CC[C@H]3C2

InChI

InChIKey=PVZMYDPRVUCJKV-CMPLNLGQSA-N

InChI=1S/C15H22N2O/c1-4-11-9(2)16-13-7-10-5-6-17(3)8-12(10)15(18)14(11)13/h10,12,16H,4-8H2,1-3H3/t10-,12+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H22N2O
Molecular Weight	246.348
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6132425 | https://www.ncbi.nlm.nih.gov/pubmed/2564788 | https://www.ncbi.nlm.nih.gov/pubmed/3549873 | https://www.ncbi.nlm.nih.gov/pubmed/2890671 | https://www.ncbi.nlm.nih.gov/pubmed/3699100 | https://www.ncbi.nlm.nih.gov/pubmed/6149457

Piquindone is an antipsychotic pyrroloisoquinoline derivative that binds to dopamine D2 receptors. It is a potent D-2 antagonist. It has a low potential for extrapyramidal effects and tardive dyskinesia. Piquindone exhibited relatively weaker cataleptogenic and antistereotypic activity than haloperidol, and had minimal activity in a rat chronic stereotypy model of receptor supersensitivity. Piquindone almost as potent as haloperidol, with fewer or less intense extrapyramidal effects and low potential for tardive dyskinesia. Piquindone led to moderate but significant improvements in the positive symptoms of schizophrenia and to improvements in negative symptoms just below the level of statistical significance. Therapeutic efficacy of a piquindone antagonist in Tourette Syndrome can be achieved without production of disabling extrapyramidal-side effects.

Approval Year

PubMed

Title	Date	PubMed
Pharmacological options for the treatment of Tourette's disorder.	2001	11772131
A multiway 3D QSAR analysis of a series of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxybenzamides.	1998-01	9570091
The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists.	1997-08	9342550
Dopamine D2 receptor model explains binding affinity of neuroleptics: piquindone and its structure activity relationships.	1996-04	8874043
Optically active benzamides as predictive tools for mapping the dopamine D2 receptor.	1990-07-31	1977603
The effect of dopamine receptor blockade on the development of sensitization to the locomotor activating effects of amphetamine and morphine.	1989-10-09	2679971
Structural requirements of Na+-dependent antidopaminergic agents: Tropapride, Piquindone, Zetidoline, and Metoclopramide. Comparison with Na+-independent ligands.	1989-03	2715795
Comparison of prolactin responses to D-1 and D-2 antagonists in rats: Ro 22-1319 is a potent D-2 antagonist.	1989-02-15	2564788
The induction of grooming and vacuous chewing by a series of selective D-1 dopamine receptor agonists: two directions of D-1:D-2 interaction.	1989-02-07	2565818
Alterations in sleep polygraphy after neuroleptic withdrawal: a putative supersensitive dopaminergic mechanism.	1989-01	2563233
Stereoelectronic study of zetidoline, a dopamine D2 receptor antagonist.	1989-01	2521253
Further evidence for two directions of D-1:D-2 dopamine receptor interaction revealed concurrently in distinct elements of typical and atypical behaviour: studies with the new enantioselective D-2 agonist LY 163502.	1989	2569218
Pharmacological activity profiles of dopamine D-1 and D-2 reception agonists and antagonists on striatal neuronal activity and the response to dexamphetamine in freely moving rats.	1989	2568305
Crystallographic, theoretical and molecular modelling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist.	1987-10	2891816
The efficacy of piquindone, a new atypical neuroleptic, in the treatment of the positive and negative symptoms of schizophrenia.	1987-10	2890671
The dopamine D-2 antagonist, Ro 22-1319, inhibits the persistent behavioral syndrome induced by iminodipropionitrile (IDPN) in mice.	1987-06	2953619
Effects of D2-dopaminergic receptor stimulation on male rat sexual behavior.	1987	2951493
The thermodynamics of agonist and antagonist binding to dopamine D-2 receptors.	1986-09	2943980
Improvement of symptoms in Tourette syndrome by piquindone, a novel dopamine-2 receptor antagonist.	1986-07	3549873
Locomotor behaviors in response to new selective D-1 and D-2 dopamine receptor agonists, and the influence of selective antagonists.	1986-07	3529126

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:42:50 GMT 2025` Edited by `admin` on `Mon Mar 31 18:42:50 GMT 2025`
Record UNII	O1C9WXY65C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RO 22-1319

Preferred Name

English

PIQUINDONE

Official Name

English

RO-22-1319

Code

English

(±)-TRANS-3-ETHYL-1,4A,5,6,7,8,8A,9-OCTAHYDRO-2,6-DIMETHYL-4H-PYRROLO(2,3-G)ISOQUINOLIN-4-ONE

Common Name

English

piquindone [INN]

Common Name

English

4H-PYRROLO(2,3-G)ISOQUINOLIN-4-ONE, 3-ETHYL-1,4A,5,6,7,8,8A,9-OCTAHYDRO-2,6-DIMETHYL-, (±)-

Common Name

English

Code System Code Type Description

MESH

C032412