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

• ChemBase编号: 126657
• 分子式: C18H23NO4
• 平均质量: 317.37952
• 单一同位素质量: 317.16270822
• SMILES: O=C(O[C@H]1C[C@H]2N(C)[C@@H]([C@@H]1C(=O)OCC)CC2)c1ccccc1
• Canonical SMILES: CCOC(=O)[C@@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
• InChI: InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3/t13-,14+,15-,16+/m0/s1
• InChIKey: NMPOSNRHZIWLLL-XUWVNRHRSA-N

名称和登记号

名称

• IUPAC标准名: ethyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC传统名: cocaethylene
• 别名: 乙基苯酰芽子碱; 可卡乙碱; benzoylecgonine ethyl ester; ethylbenzoylecgonine,; Cocaethylene; Cocaethylene; (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Ethyl Ester; Ecgonine Ethyl Ester Benzoate (Ester); Ethyl Benzoylecgonine; Ethylcocaine; Homocaine; Homococaine

登记号

• CAS号: 529-38-4
• MDL号: MFCD00083171
• PubChem SID: 24892289; 162220987
• PubChem CID: 644006; 65034
• CHEMBL: 608806
• Chemspider ID: 559082
• 维基百科标题: Cocaethylene

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): -0.43166134
• LogD (pH = 7.4): 1.2525958
• Log P: 2.638916
• 摩尔折射率: 85.909 cm^3
• 极化性: 34.00524 Å^3
• 极化表面积: 55.84 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Alcohol; Ether
• 外观: Crystalline Solid
• 熔点: 1090C

安全信息

• RTECS编号: CL5602980
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 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): 3
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 毒品管制信息: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 给药途径: Produced from ingestion of cocaine and ethanol
• 依赖倾向: Moderate to High
• 法定药品分级: CD (UK); Not scheduled specifically, could be prosecuted as an analogue of a scheduled substance.
• 妊娠期药物分类: C
• 相关基因信息: mouse ... Slc6a2(20538)rat ... Slc6a3(24898), Slc6a4(25553)

详细说明

Sigma Aldrich - C0932

Biochem/physiol Actions
多巴胺转运蛋白的高亲和性配体；伴随滥用酒精时可卡因的代谢物

Toronto Research Chemicals - C633400

Homolog of Cocaine (C633500). Anesthetic (local). High-affinity ligand for dopamine transporter; a metabolite of Cocaine when alcohol is concommitently abused. Controlled substance.

参考文献

• ElSohly, M., et al.: J. Anal. Toxicol., 15, 46 (1991)
• Hearn, W.L., et al.: J. Neurochem., 56, 698 (1991)
• Shimomura, E., et al.: Clin. Chem., 47, 1040 (1991)
• Wu, A.H.B., et al.: J. Anal. Toxicol., 16, 132 (1991)