(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

• ChemBase编号: 1304
• 分子式: C16H19NO4
• 平均质量: 289.32636
• 单一同位素质量: 289.13140809
• SMILES: O([C@@H]1[C@@H]([C@@H]2N([C@@H](CC2)C1)C)C(=O)O)C(=O)c1ccccc1
• Canonical SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)O
• InChI: InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1
• InChIKey: GVGYEFKIHJTNQZ-RFQIPJPRSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• IUPAC传统名: ecgonine benzoate; benzoylecgonine
• 别名: 苯甲酰芽子碱 溶液; (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid; Benzoyl Ecgonine; Benzoylecgonine solution; BCG; BEG; Benzoylecgonine hydrate; Benzoylecgonine solution; Benzoylecogonine; Ecgonine benzoate; O-benzoyl-(-)-ecgonine; O-benzoylecgonine; (-)-benzoylecgonine; Benzoylecgonine

登记号

• CAS号: 519-09-5
• MDL号: MFCD00070263
• PubChem SID: 46508112; 160964764; 24892104
• PubChem CID: 448223
• CHEBI ID: 41001
• Chemspider ID: 395095
• DrugBank ID: DB01515
• KEGG ID: C10847
• 美国药典/FDA物质标识码: 5353I8I6YS
• 维基百科标题: Benzoylecgonine

理论计算性质

JChem

• Acid pKa: 3.1464374
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -0.59588516
• LogD (pH = 7.4): -0.59690845
• Log P: -0.59486806
• 摩尔折射率: 76.3913 cm^3
• 极化性: 30.082672 Å^3
• 极化表面积: 66.84 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.71
• LOG S: -1.88
• 溶解度: 3.82e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; Ethanol; Methanol
• 外观: White Solid
• 熔点: 1950C (dec)
• 闪点: 11 °C; 51.8 °F

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T)
• 联合国危险货物编号: 1230
• 德国WGK号: 1
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-23/24/25-39/23/24/25
• 安全公开号: 16-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H301-H311-H331-H370
• GHS警示性声明: P210-P260-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2
• 毒品管制信息: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: rat ... Slc6a3(24898)

产品相关信息

• 浓度: 1.0 mg/mL±5% in methanol
• 级别: analytical standard, for drug analysis

详细说明

DrugBank - DB01515

• Drug Groups: illicit; experimental
• Description: Benzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases. It is excreted in the urine of cocaine users after processing in the liver. [Wikipedia]
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Toronto Research Chemicals - B208125

A metabolite of Cocaine. Controlled substance.

参考文献

• Wolff, K., et al.: Addiction, 94, 1279 (1999)
• Schaffer, M., et al.: J. Anal. Toxicol., 29, 319 (1999)
• Cognard, E., et al.: J. Pharm. Biomed. Anal., 41, 925(1999)