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 hydrochloride

• ChemBase编号: 72997
• 分子式: C21H27ClN2O3
• 平均质量: 390.90368
• 单一同位素质量: 390.17102041
• SMILES: [nH]1c2c(c3c1cccc3)CCN1[C@H]2C[C@H]2[C@H](C1)CC[C@@H]([C@@H]2C(=O)OC)O.Cl
• Canonical SMILES: COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1.Cl
• InChI: InChI=1S/C21H26N2O3.ClH/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;1H/t12-,15-,17-,18-,19+;/m0./s1
• InChIKey: PIPZGJSEDRMUAW-VJDCAHTMSA-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^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate hydrochloride; 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 hydrochloride
• IUPAC传统名: yohimbine hydrochloride
• 别名: 姬姆氏色素; Antagonil; Yohimbe; Aphrodine hydrochloride; Yohimbine monohydrochloride; Yohimbine hydrochloride; Giemsa Stain; (16α,17α)-17-Hydroxy-yohimban-16-carboxylic Acid Methyl Ester Hydrochloride; Actibine; Aphrodyne; Dayto-Himbin; Erex; NIH 9689; NSC 19509; Thybine; Yocon; Yohimbine Chloride; Yohimex; Yomax; 17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride; Yohimbine hydrochloride; (1R,2S,4aR,13bS,14aS)-methyl 2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride

登记号

• CAS号: 51811-82-6; 65-19-0
• EC号: 257-438-2; 200-600-4
• MDL号: MFCD00012674; MFCD00081642
• PubChem SID: 24277814; 162037917
• PubChem CID: 6169

理论计算性质

• Acid pKa: 14.676982
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.037232514
• LogD (pH = 7.4): 1.6539497
• 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

分子性质

理化性质

• 溶解度: DMSO; H2O: soluble10 mg/mL; Methanol
• 外观: Pale Beige Solid; white to off-white powder
• 熔点: 266-269°C; 288-290 °C (dec.)(lit.); ca 300°C

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: ZG1015000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 23/24/25
• 安全公开号: 22-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H311-H331
• GHS警示性声明: P261-P264-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2

药理学性质

• 相关基因信息: human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)

产品相关信息

• 纯度: ≥98% (TLC)
• 成盐信息: HCl; ydrochloride
• 分类: Genuine Natural Compounds

详细说明

Selleck Chemicals - S2373

Research Area: Endocrinology
Biological Activity:
Yohimbine(Antagonil) has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. Yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. [1]

Sigma Aldrich - Y3125

Biochem/physiol Actions
α2-adrenoceptor antagonist.

Toronto Research Chemicals - Y100800

Indole alkaloid with α2-adrenergic blocking activity. Mydriatic. Used in the treatment of neurological disorders.

参考文献

• http://www.drugbank.ca/drugs/DB01392
• Mekkawi, A.G., Anal. Profile Drug Subs., 16, 731 (1986)
• Goldberg, M.R., et al.: Pharmacol. Rev., 35, 143 (1986)
• Morales, A., et al.: J. Urol., 137, 1168 (1986)