(-)-Quinpirole hydrochloride

• Catalog No.: Q102
• CAS Number: 85798-08-9
• M. F.: C13H22ClN3
• M. W.: 255.78688
• Purity: ≥98% (HPLC)

SYNONYMS

• IUPAC name: (4aR,8aR)-5-propyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride
• IUPAC Traditional name: (4aR,8aR)-5-propyl-2H,4H,4aH,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride
• Synonyms: LY-171,555; (–)-Quinpirole monohydrochloride; trans-(–)-(4aR)-4,4a,5,6,7,8,8a,9-Octahydro-5-propyl-1H-pyrazolo[3,4-g]quinoline monohydrochloride

DATABASE IDS

• MDL Number: MFCD00069336
• PubChem SID: 24277929
• CAS Number: 85798-08-9

PROPERTIES

• Purity: ≥98% (HPLC)
• Gene Information: human ... DRD2(1813), DRD3(1814)
• Apperance: white solid
• Optical Rotation: [α]25/D -124.5°, c = 0.4 in H2O(lit.)
• Solubility: 0.1 M HCl: soluble23 mg/mL
• Solubility: H2O: soluble7.3 mg/mL
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RTECS: UR0809270
• Storage Temperature: -20°C
• German water hazard class: 3

DETAILS

Description (English)

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