methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

• ChemBase编号: 1203
• 分子式: C21H26N2O3
• 平均质量: 354.44274
• 单一同位素质量: 354.1943427
• SMILES: O[C@@H]1[C@@H]([C@@H]2[C@H](CN3[C@@H](C2)c2[nH]c4c(c2CC3)cccc4)CC1)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
• InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
• InChIKey: BLGXFZZNTVWLAY-SCYLSFHTSA-N

名称和登记号

名称

• IUPAC标准名: methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate; methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• IUPAC传统名: yohimbine
• 商标名: Yocon; Yohimar; Yohimex; Yoman; Yovital; Thybine; Actibine; Baron-X; Dayto himbin; Aphrodyne
• 别名: Yohimbine; Yohimbin; Yohimbine

登记号

• CAS号: 146-48-5
• PubChem SID: 46504602; 160964665
• PubChem CID: 8969
• CHEBI ID: 10093
• ATC码: G04BE04; QV03AB93
• CHEMBL: 15245
• Chemspider ID: 8622
• DrugBank ID: DB01392
• IUPHAR配体索引: 102
• 美国药典/FDA物质标识码: 2Y49VWD90Q
• 维基百科标题: Yohimbine

理论计算性质

JChem

• Acid pKa: 14.676982
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 0.09948015
• LogD (pH = 7.4): 1.7400687
• Log P: 2.0986583
• 摩尔折射率: 99.631 cm^3
• 极化性: 40.114906 Å^3
• 极化表面积: 65.56 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.36
• LOG S: -3.01
• 溶解度: 3.48e-01 g/l

分子性质

理化性质

• 外观: Powder
• 疏水性(logP): 2.73 [HANSCH,C ET AL. (1995)]

药理学性质

• 给药途径: Oral
• 法定药品分级: OTC

详细说明

DrugBank - DB01392

• Drug Groups: approved
• Description: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. [PubChem]
• Indication: Indicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.
• Pharmacology: Yohimbine is an indolalkylamine alkaloid with chemical similarity to reserpine. Yohimbine blocks presynaptic alpha-2 adrenergic receptors. Its action on peripheral blood vessels resembles that of reserpine, though it is weaker and of short duration. Yohimbine's peripheral autonomic nervous system effect is to increase parasympathetic (cholinergic) and decrease sympathetic (adrenergic) activity. It is to be noted that in male sexual performance, erection is linked to cholinergic activity and to alpha-2 adrenergic blockade which may theoretically result in increased penile inflow, decreased penile outflow or both. Yohimbine exerts a stimulating action on the mood and may increase anxiety. Such actions have not been adequately studied or related to dosage although they appear to require high doses of the drug. Yohimbine has a mild anti-diuretic action, probably via stimulation of hypothalmic center and release of posterior pituitary hormone. Reportedly Yohimbine exerts no significant influence on cardiac stimulation and other effects mediated by (beta)-adrenergic receptors. Its effect on blood pressure, if any, would be to lower it; however, no adequate studies are at hand to quantitate this effect in terms of Yohimbine dosage.
• Affected Organisms: Humans and other mammals
• Biotransformation: Yohimbine appears to undergo extensive metabolism in an organ of high flow such as the liver or kidney, however, the precise metabolic fate of yohimbine has not been fully determined.
• Absorption: Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).
• Half Life: Elimination half-life is approximately 36 minutes.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com