Skip to Content
Merck
All Photos(1)

Documents

Q102

Sigma-Aldrich

(−)-Quinpirole hydrochloride

≥98% (HPLC), solid

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C13H21N3 · HCl
CAS Number:
Molecular Weight:
255.79
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hiroyoshi Inaba et al.
Neuropsychopharmacology reports, 41(3), 405-415 (2021-07-24)
A reduced mismatch negativity (MMN) response is a promising electrophysiological endophenotype of schizophrenia that reflects neurocognitive impairment. Dopamine dysfunction is associated with symptoms of schizophrenia. However, whether the dopamine system is involved in MMN impairment remains controversial. In this study
Laszlo Peczely et al.
The international journal of neuropsychopharmacology, 25(7), 590-599 (2022-03-30)
The ventral pallidum (VP) is a dopaminoceptive forebrain structure regulating the ventral tegmental area (VTA) dopaminergic population activity. We have recently demonstrated that in the VP, the D2-like dopamine (DA) receptor agonist quinpirole dose dependently facilitates memory consolidation in inhibitory
Role of D2 dopamine receptors of the ventral pallidum in inhibitory avoidance learning
Lenard L, et al.
Behavioural Brain Research, 321, 99-105 (2017)
Víctor Fernández-Dueñas et al.
Journal of neurochemistry, 123(3), 373-384 (2012-08-29)
In the CNS, an antagonistic interaction has been shown between adenosine A(2A) and dopamine D(2) receptors (A(2A)Rs and D(2)Rs) that may be relevant both in normal and pathological conditions (i.e., Parkinson's disease). Thus, the molecular determinants mediating this receptor-receptor interaction
Role of ventral pallidal D2 dopamine receptors in the consolidation of spatial memory
Peczely L, et al.
Behavioural Brain Research, 313, 1-9 (2016)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service