Q102

(−)-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
• Empirical Formula (Hill Notation): C₁₃H₂₁N₃ · HCl
• CAS Number: 85798-08-9
• Molecular Weight: 255.79
• MDL number: MFCD00069336
• UNSPSC Code: 12352200
• PubChem Substance ID: 24277929
• NACRES: NA.77

Properties

• 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)

Description

Application

(-)-Quinpirole hydrochloride has been used as a selective D2 dopamine (DA) receptor agonist in various experiments.[1][2][3]

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 (K_D = 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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves