(4aR,8aR)-5-propyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride

• ChemBase编号: 134069
• 分子式: C13H22ClN3
• 平均质量: 255.78688
• 单一同位素质量: 255.1502254
• SMILES: CCCN1CCC[C@H]2[C@H]1Cc1c[nH]nc1C2.Cl
• Canonical SMILES: CCCN1CCC[C@H]2[C@H]1Cc1c[nH]nc1C2.Cl
• InChI: 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
• InChIKey: HJHVRVJTYPKTHX-HTMVYDOJSA-N

名称和登记号

名称

• IUPAC标准名: (4aR,8aR)-5-propyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride
• IUPAC传统名: (4aR,8aR)-5-propyl-2H,4H,4aH,6H,7H,8H,8aH,9H-pyrido[2,3-f]indazole hydrochloride
• 别名: (–)-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; (-)-Quinpirole hydrochloride

登记号

• CAS号: 85798-08-9
• MDL号: MFCD00069336
• PubChem SID: 24277929; 162228346
• PubChem CID: 55397

理论计算性质

• 里宾斯基五规则: true
• Acid pKa: 16.111439
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -1.3089768
• LogD (pH = 7.4): -0.31849062
• Log P: 2.140967
• 摩尔折射率: 66.8137 cm^3
• 极化性: 25.464058 Å^3
• 极化表面积: 31.92 Å^2
• 可自由旋转的化学键: 2

分子性质

理化性质

• 溶解度: 0.1 M HCl: soluble23 mg/mL; H2O: soluble7.3 mg/mL
• 外观: white solid
• 比旋光度: [α]25/D -124.5°, c = 0.4 in H2O(lit.)

安全信息

• RTECS编号: UR0809270
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... DRD2(1813), DRD3(1814)

产品相关信息

• 纯度: ≥98% (HPLC)

详细说明

Sigma Aldrich - Q102

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.