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Details

Stereochemistry ACHIRAL
Molecular Formula C13H15N3.C4H4O4
Molecular Weight 329.3505
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of QUIPAZINE MALEATE

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 C13H15N3
Molecular Weight 213.2783
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

PubMed

PubMed

TitleDatePubMed
Synthesis of a fluorine-18-labelled derivative of 6-nitroquipazine, as a radioligand for the in vivo serotonin transporter imaging with PET.
2002 Aug
Synthesis, radiolabeling and preliminary biological evaluation of radiolabeled 5-methyl-6-nitroquipazine, a potential radioligand for the serotonin transporter.
2002 Dec 16
The Interactions of the 5-HT(3) receptor with arylpiperazine, tropane, and quinuclidine ligands.
2002 Jun
Electroencephalographic activation by tacrine, deprenyl, and quipazine: cholinergic vs. non-cholinergic contributions.
2002 Jun 28
Serotonergic attenuation of the reinforcing and neurochemical effects of cocaine in squirrel monkeys.
2002 Mar
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 2: 4-substituted 6-nitroquipazines.
2002 Mar 11
Serotonin sets the day state in the neurons that control coupling between the optic lobe circadian pacemakers in the cricket Gryllus bimaculatus.
2002 May
Stimulus generalization by fenfluramine in a quipazine-ketanserin drug discrimination is not dependent on indirect serotonin release.
2002 May
5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens.
2002 May
Response of the mouse circadian system to serotonin 1A/2/7 agonists in vivo: surprisingly little.
2003 Apr
Biochemical evidence for the presence of serotonin transporters in the rat cochlea.
2003 Aug
Role of 5-HT3 receptors in the mechanisms of central pain syndrome.
2003 Jun
Thyrotropin-releasing hormone mediates serotonin-induced secretion of GH in cattle.
2003 Mar
Puerarin acts through brain serotonergic mechanisms to induce thermal effects.
2004 Dec
Turning behaviour induced by stimulation of the 5-HT receptors in the subthalamic nucleus.
2004 Jan
Role of NMDA receptor activation in serotonin agonist-induced air-stepping in paraplegic mice.
2004 Mar
Subunit rotation models activation of serotonin 5-HT3AB receptors by agonists.
2004 Oct
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.
2004 Oct
Developmental alterations in serotoninergic neurotransmission in Borna disease virus (BDV)-infected rats: a multidisciplinary analysis.
2004 Oct
Environmental programming of stress responses through DNA methylation: life at the interface between a dynamic environment and a fixed genome.
2005
N1/P2 component of auditory evoked potential reflect changes of the brain serotonin biosynthesis in rats.
2005 Aug
Spinal cord-transected mice learn to step in response to quipazine treatment and robotic training.
2005 Dec 14
Serotonin receptor mechanisms mediate the discriminative stimulus properties of the atypical antipsychotic clozapine in C57BL/6 mice.
2005 Jun
Structure-affinity relationship studies on arylpiperazine derivatives related to quipazine as serotonin transporter ligands. Molecular basis of the selectivity SERT/5HT3 receptor.
2005 May 16
Is the platelet serotonin transporter different in venous vs. arterial blood?
2005 Nov
Design and synthesis of long-chain arylpiperazines with mixed affinity for serotonin transporter (SERT) and 5-HT(1A) receptor.
2005 Oct
Effects of 5-HT2A receptor stimulation on the discrimination of durations by rats.
2006 Feb
Increased serotonergic functions following adminstration of 1-(1-naphthyl) piperazine in propranolol injected rats.
2006 Jul
Effect of robotic-assisted treadmill training and chronic quipazine treatment on hindlimb stepping in spinally transected rats.
2006 Jul
Presynaptic serotonergic modulation of 5-HT and acetylcholine release in the hippocampus and the cortex of 5-HT1B-receptor knockout mice.
2006 Jun 15
Implications of assist-as-needed robotic step training after a complete spinal cord injury on intrinsic strategies of motor learning.
2006 Oct 11
Behavioral and neuropharmacological evidence that serotonin crosses the blood-brain barrier in Coturnix japonica (Galliformes; Aves).
2007 Feb
5-HT3 receptor-mediated photic-like responses of the circadian clock in the rat.
2007 Feb
Presynaptic modulation of 5-HT release in the rat septal region.
2007 May 11
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 5: 2'-Substituted 6-nitroquipazines.
2007 May 15
Anxiolytics may promote locomotor function recovery in spinal cord injury patients.
2008 Aug
Role of spinal 5-HT2 receptor subtypes in quipazine-induced hindlimb movements after a low-thoracic spinal cord transection.
2008 Dec
Synthesis and biological evaluation of one novel technetium-99m-labeled nitroquipazine derivative as an imaging agent for serotonin transporter.
2008 Dec
Synthesis and preliminary pharmacological evaluation of N-2-(4-(4-(2-substitutedthiazol-4-yl) piperazin-1-yl)-2-oxoethyl)acetamides as novel atypical antipsychotic agents.
2008 Dec 1
Conservation of structure, signaling and pharmacology between two serotonin receptor subtypes from decapod crustaceans, Panulirus interruptus and Procambarus clarkii.
2008 Jan
Quantification of deficits in lateral paw positioning after spinal cord injury in dogs.
2008 Nov 25
Synthesis, potency, and in vivo evaluation of 2-piperazin-1-ylquinoline analogues as dual serotonin reuptake inhibitors and serotonin 5-HT1A receptor antagonists.
2009 Aug 13
Serotonin receptor agonist quipazine promotes proliferation and apoptosis of human hepatocyte strain of L-02 strain.
2009 Jun
Specific targeting of peripheral serotonin 5-HT(3) receptors. Synthesis, biological investigation, and structure-activity relationships.
2009 Jun 11
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
Transformation of nonfunctional spinal circuits into functional states after the loss of brain input.
2009 Oct
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
Morphofunctional study of injured spinal cord of rats after activation of serotonergic receptors and motor load.
2009 Sep-Oct
Facilitation of postural limb reflexes with epidural stimulation in spinal rabbits.
2010 Feb
A novel 5-HT(2A) receptor antagonist exhibits antidepressant-like effects in a battery of rodent behavioural assays: approaching early-onset antidepressants.
2010 Jan
Patents

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 Tue Oct 22 06:02:18 UTC 2019
Edited
by admin
on Tue Oct 22 06:02:18 UTC 2019
Record UNII
JY444CK9IG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUIPAZINE MALEATE
USAN  
USAN  
Official Name English
QUIPAZINE MALEATE [USAN]
Common Name English
MA 1291
Code English
MA-1291
Code English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
Code System Code Type Description
CAS
5786-68-5
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
PRIMARY
EPA CompTox
5786-68-5
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
PRIMARY
NCI_THESAURUS
C66502
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
PRIMARY
ChEMBL
CHEMBL18772
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
PRIMARY
ECHA (EC/EINECS)
227-314-2
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
PRIMARY
PUBCHEM
5702242
Created by admin on Tue Oct 22 06:02:18 UTC 2019 , Edited by admin on Tue Oct 22 06:02:18 UTC 2019
PRIMARY
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ACTIVE MOIETY