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Q102 Sigma

(−)-Quinpirole hydrochloride

≥98% (HPLC), solid

Synonym: (–)-Quinpirole monohydrochloride, trans-(–)-(4aR)-4,4a,5,6,7,8,8a,9-Octahydro-5-propyl-1H-pyrazolo[3,4-g]quinoline monohydrochloride, LY-171,555

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Properties

Related Categories Agonists, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology,
InChI Key   HJHVRVJTYPKTHX-HTMVYDOJSA-N
assay   ≥98% (HPLC)
form   solid
optical activity   [α]25/D −124.5°, c = 0.4 in H2O(lit.)
color   white
solubility   0.1 M HCl: 23 mg/mL
  H2O: 7.3 mg/mL
storage temp.   −20°C
Gene Information   human ... DRD2(1813), DRD3(1814)

Description

Packaging

10, 25, 100 mg in glass bottle

Legal Information

Manufactured and sold with the permission of Eli Lilly and Company.

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Biochem/physiol Actions

The putative D2 dopamine receptor agonist quinpirole (LY 171,555) is the most widely used D2 agonist in in vivo and in vitro studies Active enantiomer of (±)-quinpirole. Quinpirole is a dopamine agonist with high affinity for the D2 and D3 dopamine receptor subtypes. Specific [3H]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 +/- 0.3 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. The MAOIs clorgyline and Ro 41-1049 were the most potent. MAOIs interact with a novel binding site that is labeled by [3H]quinpirole or that modulates [3H]quinpirole binding. This site may be associated with D2-like dopamine receptors.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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Safety Information

RIDADR 
NONH for all modes of transport
Protocols & Articles
Peer-Reviewed Papers
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