Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H21N3 |
Molecular Weight | 219.3259 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CCCN(CCC)[C@]1([H])CC3=C(C2)NN=C3
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
Molecular Formula | C13H21N3 |
Molecular Weight | 219.3259 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8099277Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8099277
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24831693 |
9.8 nM [EC50] | ||
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24831693 |
19.0 nM [EC50] | ||
Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17154515 |
|||
Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12617906 |
9.9 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Systemic hemodynamic and regional blood flow effects of LY141865, a selective dopamine receptor agonist. | 1984 Sep |
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Blockade of both D-1 and D-2 dopamine receptors may induce catalepsy in mice. | 1991 |
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Effect of D1 and D2 agonists and antagonists on dyskinesia produced by L-dopa in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated monkeys. | 1991 Oct |
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Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor. | 1992 Apr 10 |
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Strain differences in clonidine-induced aggressiveness in mice and its interaction with the dopamine system. | 1993 Apr |
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Striatal Fos expression is indicative of dopamine D1/D2 synergism and receptor supersensitivity. | 1993 Aug 15 |
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Depression of high-threshold calcium currents by activation of human D2 (short) dopamine receptors expressed in differentiated NG108-15 cells. | 1994 Apr |
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Rapid development of D1 and D2 dopamine receptor supersensitivity as indicated by striatal and pallidal Fos expression. | 1994 Sep 26 |
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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 |
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Neuropharmacological profile of EMD 57445, a sigma receptor ligand with potential antipsychotic activity. | 1996 Nov 21 |
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The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved? | 1999 |
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Dopamine D2/D3 receptors modulate cocaine's reinforcing and discriminative stimulus effects in rhesus monkeys. | 1999 Apr 1 |
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Enhanced vulnerability to cocaine self-administration is associated with elevated impulse activity of midbrain dopamine neurons. | 2000 Dec 1 |
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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 |
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Effect of olanzapine on functional responses from sensitized D1-dopamine receptors in rats with neonatal dopamine loss. | 2001 Aug |
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Blockade of spinal dopamine D2 receptors enhances the pressor effect of intravenous quinpirole in normotensive, conscious rats. | 2002 Feb |
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Presynaptic control of striatal dopamine neurotransmission in adult vesicular monoamine transporter 2 (VMAT2) mutant mice. | 2003 May |
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Haloperidol, but not clozapine, produces dramatic catalepsy in delta9-THC-treated rats: possible clinical implications. | 2003 Oct |
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Dyskinesias occur in response to saline and naltrexone alone after priming with combination of dopaminergic agents and naltrexone in the MPTP parkinsonian monkeys. | 2005 Jun-Jul |
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Role of cannabinoid type 1 receptors in locomotor activity and striatal signaling in response to psychostimulants. | 2007 Jun 27 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28434589
0.5 mg/kg (two injections/week)
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9806217
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
Edited
Fri Dec 15 16:44:43 UTC 2023
by
admin
on
Fri Dec 15 16:44:43 UTC 2023
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Record UNII |
20OP60125T
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C66884
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CHEMBL240773
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D019257
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C152128
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100000080281
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75401
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20OP60125T
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54562
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QUINPIROLE
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DTXSID9048229
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5610
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SUB10221MIG
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80373-22-4
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
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ACTIVE MOIETY |