QUIPAZINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H15N3.C4H4O4
Molecular Weight	329.3505
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.C1CN(CCN1)C2=CC=C3C=CC=CC3=N2

InChI

InChIKey=QYJJDHZHSCTBII-BTJKTKAUSA-N

InChI=1S/C13H15N3.C4H4O4/c1-2-4-12-11(3-1)5-6-13(15-12)16-9-7-14-8-10-16;5-3(6)1-2-4(7)8/h1-6,14H,7-10H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C13H15N3
Molecular Weight	213.2783
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C61919 | https://www.ncbi.nlm.nih.gov/pubmed/7192759

Quizapine is a piperazine-based nonselective serotonin (5-HT) receptor agonist with antidepressant and oxytocic activities. Quipazine targets and binds to serotonin receptors, particularly to the 5HT2A and 5HT3 receptors. Quipazine is a potential anti-parkinsonian agent. Serotonin receptor activation by quipazine may lead to smooth muscle contraction and antidepressant effects. quipazine, a central serotonergic agent, counteracted some of the drug-induced symptoms of pseudoparkinsonism in laboratory animals. Cholinergic, dopaminergic and histaminergic receptors play an important role in the manifestations of these symptoms.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 2b (5-HT2b) receptor 60 Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Agonist 2678	7.07 null [pKi]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Agonist 2678	6.89 null [pKi]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15322733	Agonist 2678	7.27 null [pKi]
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10543880	Agonist 2678	1.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7192759 http://www.sciencedirect.com/science/article/pii/0024320573902853	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of drugs influencing central serotonergic mechanisms on haloperidol-induced catalepsy.	1979 Mar 29	108749
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.	1999 May	10217294
RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity.	2001 Sep	11564657
Locomotor recovery in the chronic spinal rat: effects of long-term treatment with a 5-HT2 agonist.	2002 Aug	12193190
Stimulus generalization by fenfluramine in a quipazine-ketanserin drug discrimination is not dependent on indirect serotonin release.	2002 May	11900772
Response of the mouse circadian system to serotonin 1A/2/7 agonists in vivo: surprisingly little.	2003 Apr	12693869
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter: Part 3. A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine.	2003 Nov 17	14604657
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004 Aug	15322733
Synergistic activation of the central pattern generator for locomotion by l-beta-3,4-dihydroxyphenylalanine and quipazine in adult paraplegic mice.	2004 Mar 25	15026151
N1/P2 component of auditory evoked potential reflect changes of the brain serotonin biosynthesis in rats.	2005 Aug	16491646
Long-lasting recovery of locomotor function in chronic spinal rat following chronic combined pharmacological stimulation of serotonergic receptors with 8-OHDPAT and quipazine.	2005 Aug 12-19	15905027
Serotonin receptor mechanisms mediate the discriminative stimulus properties of the atypical antipsychotic clozapine in C57BL/6 mice.	2005 Jun	15696329
Serotonin-related enhancement of recovery of hind limb motor functions in spinal rats after grafting of embryonic raphe nuclei.	2005 May	15892603
Implications of assist-as-needed robotic step training after a complete spinal cord injury on intrinsic strategies of motor learning.	2006 Oct 11	17035542
Acute and constitutive increases in central serotonin levels reduce social play behaviour in peri-adolescent rats.	2007 Dec	17661017
[Effect of local microapplication of serotoninergic drugs on membrane currents of Paracentrotus lividus early embryos].	2007 Jul-Aug	17915534
5-HT-receptive structures are localized in the interblastomere cleft of Paracentrotus lividus early embryos.	2008 Feb	18221585
Dose dependence of the 5-HT agonist quipazine in facilitating spinal stepping in the rat with epidural stimulation.	2008 Jun 27	18490105
Serotonin receptor agonist quipazine promotes proliferation and apoptosis of human hepatocyte strain of L-02 strain.	2009 Jun	19502168
Synthesis and preliminary screening of novel N-{2-[4-(substituted)piperazin-1-yl]-2-oxoethyl}acetamides as potential atypical antipsychotic agents.	2009 Jun	18825551
Effects of serotonergic agents on survival and hemolymph composition of the larval mosquito Aedes aegypti (Diptera: Culicidae, L.) in vivo: does serotonin regulate hemolymph acid-base homeostasis?	2009 Nov	19880735
Transformation of nonfunctional spinal circuits into functional states after the loss of brain input.	2009 Oct	19767747
Morphofunctional study of injured spinal cord of rats after activation of serotonergic receptors and motor load.	2009 Sep-Oct	19994777
A novel 5-HT(2A) receptor antagonist exhibits antidepressant-like effects in a battery of rodent behavioural assays: approaching early-onset antidepressants.	2010 Jan	19800913

Patents

Sample Use Guides

In Vivo Use Guide

Rats: Quipazine increased serum corticosterone within 30 min after its i.p. injection (at 10 mg/kg) into rats. Elevation of serum corticosterone did not occur with a 1.25 mg/kg dose of quipazine but was dose-related over a 2.5-20 mg/kg dose range.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Quipazine (3.1 x 10(-7)-10(-4) M) caused concentration-dependent contractions of the canine basilar artery.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:01:48 UTC 2023` Edited by `admin` on `Fri Dec 15 16:01:48 UTC 2023`
Record UNII	JY444CK9IG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

QUIPAZINE MALEATE

Official Name

English

NSC-758469

Code

English

2-(1-Piperazinyl)quinoline maleate (1:1)

Systematic Name

English

QUIPAZINE MALEATE [USAN]

Common Name

English

MA 1291

Code

English

MA-1291

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47794