QUIPAZINE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

C1CN(CCN1)C2=CC=C3C=CC=CC3=N2

InChI

InChIKey=XRXDAJYKGWNHTQ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

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
Environmental programming of stress responses through DNA methylation: life at the interface between a dynamic environment and a fixed genome.	2005	16262207
Involvement of the retinohypothalamic tract in the photic-like effects of the serotonin agonist quipazine in the rat.	2005	16084651
N1/P2 component of auditory evoked potential reflect changes of the brain serotonin biosynthesis in rats.	2005 Aug	16491646
Hyperglycemia induced by pharmacological activation of central serotonergic pathways depends on the functional integrity of brain CRH system and 5-HT3 receptors.	2005 Aug	16138260
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
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines.	2005 Aug 15	15993088
Preclinical pharmacology of FMPD [6-fluoro-10-[3-(2-methoxyethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene]: a potential novel antipsychotic with lower histamine H1 receptor affinity than olanzapine.	2005 Dec	16141369
Spinal cord-transected mice learn to step in response to quipazine treatment and robotic training.	2005 Dec 14	16354932
The serotonergic agonists quipazine, CGS-12066A, and alpha-methylserotonin alter motor activity and induce hindlimb stepping in the intact and spinal rat fetus.	2005 Jun	15998204
Characterization of serotonin 5-HT2C receptor signaling to extracellular signal-regulated kinases 1 and 2.	2005 Jun	15935077
Serotonin-related enhancement of recovery of hind limb motor functions in spinal rats after grafting of embryonic raphe nuclei.	2005 May	15892603
Is the platelet serotonin transporter different in venous vs. arterial blood?	2005 Nov	16341932
Design and synthesis of long-chain arylpiperazines with mixed affinity for serotonin transporter (SERT) and 5-HT(1A) receptor.	2005 Oct	16259761
Effects of 5-HT2A receptor stimulation on the discrimination of durations by rats.	2006 Feb	16377963
Increased serotonergic functions following adminstration of 1-(1-naphthyl) piperazine in propranolol injected rats.	2006 Jul	16935825
Effect of robotic-assisted treadmill training and chronic quipazine treatment on hindlimb stepping in spinally transected rats.	2006 Jul	16866627
Presynaptic serotonergic modulation of 5-HT and acetylcholine release in the hippocampus and the cortex of 5-HT1B-receptor knockout mice.	2006 Jun 15	16750486
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
Behavioral and neuropharmacological evidence that serotonin crosses the blood-brain barrier in Coturnix japonica (Galliformes; Aves).	2007 Feb	17505765
5-HT3 receptor-mediated photic-like responses of the circadian clock in the rat.	2007 Feb	17084866
[Effect of local microapplication of serotoninergic drugs on membrane currents of Paracentrotus lividus early embryos].	2007 Jul-Aug	17915534
Presynaptic modulation of 5-HT release in the rat septal region.	2007 May 11	17383104
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
Anxiolytics may promote locomotor function recovery in spinal cord injury patients.	2008 Aug	19043520
Effect of intrathecal administration of serotoninergic and noradrenergic drugs on postural performance in rabbits with spinal cord lesions.	2008 Aug	18497353
Role of spinal 5-HT2 receptor subtypes in quipazine-induced hindlimb movements after a low-thoracic spinal cord transection.	2008 Dec	19019202
Synthesis and biological evaluation of one novel technetium-99m-labeled nitroquipazine derivative as an imaging agent for serotonin transporter.	2008 Dec	18684634
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	18948000
5-HT-receptive structures are localized in the interblastomere cleft of Paracentrotus lividus early embryos.	2008 Feb	18221585
Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys.	2008 Feb	17993605
5-Fluorotryptamine is a partial agonist at 5-HT3 receptors, and reveals that size and electronegativity at the 5 position of tryptamine are critical for efficient receptor function.	2008 Feb 12	18082160
Conservation of structure, signaling and pharmacology between two serotonin receptor subtypes from decapod crustaceans, Panulirus interruptus and Procambarus clarkii.	2008 Jan	18083737
Step training reinforces specific spinal locomotor circuitry in adult spinal rats.	2008 Jul 16	18632941
Facilitation of stepping with epidural stimulation in spinal rats: role of sensory input.	2008 Jul 30	18667609
A hydrogen bond in loop A is critical for the binding and function of the 5-HT3 receptor.	2008 Jun 17	18498149
Dose dependence of the 5-HT agonist quipazine in facilitating spinal stepping in the rat with epidural stimulation.	2008 Jun 27	18490105
Location and orientation of serotonin receptor 1a agonists in model and complex lipid membranes.	2008 Mar 21	18187421
Quantification of deficits in lateral paw positioning after spinal cord injury in dogs.	2008 Nov 25	19032742
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
Synthesis and preliminary screening of novel N-{2-[4-(substituted)piperazin-1-yl]-2-oxoethyl}acetamides as potential atypical antipsychotic agents.	2009 Jun	18825551
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
Morphofunctional study of injured spinal cord of rats after activation of serotonergic receptors and motor load.	2009 Sep-Oct	19994777
Facilitation of postural limb reflexes with epidural stimulation in spinal rabbits.	2010 Feb	20018835
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 15:14:41 GMT 2023` Edited by `admin` on `Fri Dec 15 15:14:41 GMT 2023`
Record UNII	4WCY05C0SJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUIPAZINE

Official Name

English

quipazine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794