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Q102

Sigma-Aldrich

(−)-Quinpirole hydrochloride

≥98% (HPLC), solid

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Synonym(s):
(–)-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
Empirical Formula (Hill Notation):
C13H21N3 · HCl
CAS Number:
85798-08-9
Molecular Weight:
255.79
MDL number:
MFCD00069336
PubChem Substance ID:
24277929
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]25/D −124.5°, c = 0.4 in H2O(lit.)

storage condition

desiccated

color

white

solubility

0.1 M HCl: 23 mg/mL
H2O: 7.3 mg/mL

storage temp.

−20°C

SMILES string

Cl.[H][C@]12CCCN(CCC)[C@]1([H])Cc3c[nH]nc3C2

InChI

1S/C13H21N3.ClH/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);1H/t10-,13-;/m1./s1

InChI key

HJHVRVJTYPKTHX-HTMVYDOJSA-N

Gene Information

human ... DRD2(1813) , DRD3(1814)

Application

(-)-Quinpirole hydrochloride has been used as a selective D2 dopamine (DA) receptor agonist in various experiments.

Biochem/physiol Actions

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. The putative D2 dopamine receptor agonist quinpirole (LY 171,555) is the most widely used D2 agonist in in vivo and in vitro studies. Quinpirole hydrochloride is an active enantiomer of (±)-quinpirole.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.

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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