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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H21N3
Molecular Weight 219.3264
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINPIROLE

SMILES

CCCN1CCC[C@]2([H])Cc3c(C[C@]21[H])c[nH]n3

InChI

InChIKey=FTSUPYGMFAPCFZ-ZWNOBZJWSA-N
InChI=1S/C13H21N3/c1-2-5-16-6-3-4-10-7-12-11(8-13(10)16)9-14-15-12/h9-10,13H,2-8H2,1H3,(H,14,15)/t10-,13-/m1/s1

HIDE SMILES / InChI

Molecular Formula C13H21N3
Molecular Weight 219.3264
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9806217 | https://www.ncbi.nlm.nih.gov/pubmed/2566488 | https://www.ncbi.nlm.nih.gov/pubmed/9926830 | https://www.ncbi.nlm.nih.gov/pubmed/28434589

Quinpirole (LY 171,555) is a psychoactive drug and research chemical which acts as a selective D2 and D3 receptor agonist. Quinpirole is the most widely used D2 agonist in in vivo and in vitro studies. Specific quinpirole binding in rat brain was saturable, and dependent on temperature, membrane concentration, sodium concentration and guanine nucleotides. Saturation analysis revealed high affinity binding characteristics (KD = 2.3 nM) which were confirmed by association-dissociation kinetics. The regional distribution of [3H]quinpirole binding sites roughly paralleled the distribution of [3H]spiperone binding sites, with greatest densities present in the striatum, nucleus accumbens and olfactory tubercles. A variety of drugs, most notably monoamine oxidase inhibitors (MAOls), inhibit the binding of [3H]quinpirole, but not [3H]spiperone or [3H](-)N-n-Propylnorapomorphine, in rat striatal membranes by a mechanism that does not appear to involve the enzymatic activity of MAO. Clinically antidepressant MAOIs exhibited selectivity between sites labeled by [3H]quinpirole and [3H]spiperone as did a number of structurally related propargylamines and N-acylethylenediamine derivatives and other drugs such as debrisoquin and phenylbiguanide. Quinpirole has been shown to increase locomotion and sniffing behavior in mice and induces compulsive behavior symptomatic of obsessive compulsive disorder in rats.

Originator

Sources: Brain research (1981), 225, (2), 347-56.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.8 nM [EC50]
19.0 nM [EC50]
9.9 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Rapid development of D1 and D2 dopamine receptor supersensitivity as indicated by striatal and pallidal Fos expression.
1994 Sep 26
Lack of discrimination by agonists for D2 and D3 dopamine receptors.
1995 Jul
Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors.
1995 Jun 23
Chronic L-DOPA administration induces dyskinesias in the 1-methyl-4- phenyl-1,2,3,6-tetrahydropyridine-treated common marmoset (Callithrix Jacchus).
1995 Nov
Functional correlates of dopamine D3 receptor activation in the rat in vivo and their modulation by the selective antagonist, (+)-S 14297: 1. Activation of postsynaptic D3 receptors mediates hypothermia, whereas blockade of D2 receptors elicits prolactin secretion and catalepsy.
1995 Nov
Cerebrocortical Fos expression following dopaminergic stimulation: D1/D2 synergism and its breakdown.
1996 Jul 22
Psychostimulants depress excitatory synaptic transmission in the nucleus accumbens via presynaptic D1-like dopamine receptors.
1996 Mar 1
Neuropsychopharmacological profile of remoxipride in comparison with clozapine.
1997 Jan-Feb
Repeated trimipramine induces dopamine D2/D3 and alpha1-adrenergic up-regulation.
1998
Acute nicotine pretreatment augments dopaminergic pulmonary vasodilation.
1998 Oct
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved?
1999
Cardiovascular responses to intrathecal dopamine receptor agonists in conscious DOCA-salt hypertensive rats.
1999
Quinpirole, 8-OH-DPAT and ketanserin modulate catalepsy induced by high doses of atypical antipsychotics.
1999 Nov
Dopamine D1- and D2-like receptor mechanisms in relapse to cocaine-seeking behavior: effects of selective antagonists and agonists.
2000 Aug
Estrogen priming modulates autoreceptor-mediated potentiation of dopamine uptake.
2000 Aug 11
Enhanced vulnerability to cocaine self-administration is associated with elevated impulse activity of midbrain dopamine neurons.
2000 Dec 1
D2 dopamine receptors in striatal medium spiny neurons reduce L-type Ca2+ currents and excitability via a novel PLC[beta]1-IP3-calcineurin-signaling cascade.
2000 Dec 15
Role of dopamine D3 receptors in thermoregulation: a reappraisal.
2000 Jan 17
Effects of dopaminergic agents on carrageenan hyperalgesia after intrathecal administration to rats.
2001 Apr 20
Effect of olanzapine on functional responses from sensitized D1-dopamine receptors in rats with neonatal dopamine loss.
2001 Aug
Cocaine and amphetamine depress striatal GABAergic synaptic transmission through D2 dopamine receptors.
2002 Feb
Relapse to cocaine- and heroin-seeking behavior mediated by dopamine D2 receptors is time-dependent and associated with behavioral sensitization.
2002 Jan
Morphine state-dependent learning: sensitization and interactions with dopamine receptors.
2004 Aug 23
Locomotor activity and cocaine-seeking behavior during acquisition and reinstatement of operant self-administration behavior in rats.
2005 May 28
Effect of repeated co-treatment with fluoxetine and amantadine on the behavioral reactivity of the central dopamine and serotonin system in rats.
2009 Sep-Oct
Amphetamine up-regulates activator of G-protein signaling 1 mRNA and protein levels in rat frontal cortex: the role of dopamine and glucocorticoid receptors.
2010 Jun 16
The role of the dopamine transporter in dopamine-induced DNA damage.
2011 May
Patents

Patents

Sample Use Guides

0.5 mg/kg (two injections/week)
Route of Administration: Other
In Vitro Use Guide
Adult, male, Sprague-Dawley rats (200-250g; Harlan Labs, Indianapolis, IN) were sacrificed by decapitation, the brains rapidly removed and dissected on ice. Striatal tissue was homogenized in 30 vol. ice-cold 0.32 M sucrose using a glass homogenizer and Teflon pestle. The crude nuclear fraction (P1), the pellet formed from centrifugation of the pellet at 1,000 x g for 10 mitt; the crude synaptosomal fraction (P2), the pellet formed by the centrifugation of the resulting supernatant at 20,000 x g for 30 min; Subfractionation of the crude synaptosomal fraction (P2) was performed by centrifugation of freshly prepared P2 fraction suspended in 0.32 M sucrose over a discontinuous gradient of 0.8 M and 1.2 M sucrose at 110,000 x g for 70 min. Three subfractions were collected. The myelin fraction (P2A) was collected at the 0.32 M/O.8 M sucrose interface; the synaptosomal fraction (P2B) at the 0.8 /1.2 M sucrose interface; and the mitochondrial fraction (P2C), the final pellet. All resulting fractions were resuspended in assay buffer and centrifuged at 100,000 x g for 30 min. The resulting pellets were used for receptor binding assays. The final fraction pellets were resuspended in assay buffer (50 mM Tris-HCl, 5 mM KCI, 2 mM MgCl2, and 2 mM CaCl2, pH 7.4 at 23°C) to yield a final protein concentration of 400 mkg/tube. Binding assays were performed in duplicate in disposable polystyrene tubes. Saturation analyses were performed in the major subcellular fractions to determine radioligand affinity. For saturation analyses, eight concentrations of [3H]quinpirole (43 Ci/mmol; NEN DuPont Research Products, Boston, MA) were used (0.1 to 30 nM). Because [3H]quinpirole exhibited similar affinity in the major subcellular fractions, single point analyses were used for subsequent experiments. For single point studies, the final concentration of [3H]quinpirole was ~2 nM Binding was initiated by the addition of resuspended subcellular fractionate. The total assay volume was 0.5 ml. Tubes were incubated at 23°C for 4 h
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:13:11 UTC 2021
Edited
by admin
on Sat Jun 26 13:13:11 UTC 2021
Record UNII
20OP60125T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINPIROLE
INN   WHO-DD  
INN  
Official Name English
QUINPIROLE [INN]
Common Name English
(-)-(4AR,8AR)-4,4A,5,6,7,8,8A,9-OCTAHYDRO-5-PROPYL-1H-PYRAZOLO(3,4-G)QUINOLINE
Common Name English
QUINPIROLE [WHO-DD]
Common Name English
1H-PYRAZOLO(3,4-G)QUINOLINE, 4,4A,5,6,7,8,8A,9-OCTAHYDRO-5-PROPYL-, (4AR-TRANS)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL240773
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
MESH
D019257
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
NCI_THESAURUS
C152128
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
FDA UNII
20OP60125T
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
PUBCHEM
54562
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
WIKIPEDIA
QUINPIROLE
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
EPA CompTox
80373-22-4
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
INN
5610
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
EVMPD
SUB10221MIG
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
CAS
80373-22-4
Created by admin on Sat Jun 26 13:13:12 UTC 2021 , Edited by admin on Sat Jun 26 13:13:12 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY