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
Neural circuits regulating pulsatile luteinizing hormone release in the female guinea-pig: opioid, adrenergic and serotonergic interactions.	2001 Mar	11207938
Addition of a 5-HT receptor agonist to methylphenidate potentiates the reduction of [123I]FP-CIT binding to dopamine transporters in rat frontal cortex and hippocampus.	2001 Mar 1	11169768
In vitro and in vivo ligand binding to the 5HT(3) serotonin receptor characterised by time-resolved fluorescence spectroscopy.	2001 Mar 2	11828446
PET examination of [(11)C]5-methyl-6-nitroquipazine, a radioligand for visualization of the serotonin transporter.	2002 Aug	12234589
Locomotor recovery in the chronic spinal rat: effects of long-term treatment with a 5-HT2 agonist.	2002 Aug	12193190
Metachlorophenylpiperazine (m-CPP) induced intracavernous pressure responses in anaesthetized rats.	2002 Aug	12152119
Synthesis, radiolabeling and preliminary biological evaluation of radiolabeled 5-methyl-6-nitroquipazine, a potential radioligand for the serotonin transporter.	2002 Dec 16	12443787
Comparison of the potency of MDL 100,907 and SB 242084 in blocking the serotonin (5-HT)(2) receptor agonist-induced increases in rat serum corticosterone concentrations: evidence for 5-HT(2A) receptor mediation of the HPA axis.	2002 Feb	11804612
Serotonergic attenuation of the reinforcing and neurochemical effects of cocaine in squirrel monkeys.	2002 Mar	11861788
5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens.	2002 May	11900766
Biochemical evidence for the presence of serotonin transporters in the rat cochlea.	2003 Aug	12948600
Role of 5-HT3 receptors in the mechanisms of central pain syndrome.	2003 Jun	12937671
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
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.	2004 Oct	15482641
Developmental alterations in serotoninergic neurotransmission in Borna disease virus (BDV)-infected rats: a multidisciplinary analysis.	2004 Oct	15385249
N1/P2 component of auditory evoked potential reflect changes of the brain serotonin biosynthesis in rats.	2005 Aug	16491646
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines.	2005 Aug 15	15993088
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	15848758
Is the platelet serotonin transporter different in venous vs. arterial blood?	2005 Nov	16341932
[Effect of local microapplication of serotoninergic drugs on membrane currents of Paracentrotus lividus early embryos].	2007 Jul-Aug	17915534
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 5: 2'-Substituted 6-nitroquipazines.	2007 May 15	17376695
Epidural spinal cord stimulation plus quipazine administration enable stepping in complete spinal adult rats.	2007 Nov	17855582
Location and orientation of serotonin receptor 1a agonists in model and complex lipid membranes.	2008 Mar 21	18187421
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	19719241
Serotonin receptor agonist quipazine promotes proliferation and apoptosis of human hepatocyte strain of L-02 strain.	2009 Jun	19502168
Specific targeting of peripheral serotonin 5-HT(3) receptors. Synthesis, biological investigation, and structure-activity relationships.	2009 Jun 11	19425598
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
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009 Oct 23	19725810
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 GMT 2023` Edited by `admin` on `Fri Dec 15 16:01:48 GMT 2023`
Record UNII	JY444CK9IG
Record Status	`Validated (UNII)`
Record Version

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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