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

• ChemBase编号: 130672
• 分子式: C17H22ClNO4
• 平均质量: 339.81388
• 单一同位素质量: 339.12373587
• SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC.Cl
• Canonical SMILES: COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1.Cl
• InChI: InChI=1S/C17H21NO4.ClH/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11;/h3-7,12-15H,8-10H2,1-2H3;1H/t12-,13+,14-,15+;/m0./s1
• InChIKey: PIQVDUKEQYOJNR-VZXSFKIWSA-N

名称和登记号

名称

• IUPAC标准名: methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride
• IUPAC传统名: cocaine hydrochloride
• 别名: 可卡因 盐酸盐 溶液; 苯甲酰甲基芽子碱 盐酸盐; 可卡因 盐酸盐; Cocaine hydrochloride solution; Cocaine hydrochloride; Ecgonine methyl ester benzoate hydrochloride; (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester Hydrochloride; (-)-Cocaine Hydrochloride; Cocaine Muriate; NSC 25263; Sal de Merck; Cocaine Hydrochloride

登记号

• CAS号: 53-21-4
• EC号: 200-167-1
• MDL号: MFCD00058119
• PubChem SID: 162224950
• PubChem CID: 656832

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): -0.8337083
• LogD (pH = 7.4): 0.82485026
• Log P: 2.282108
• 摩尔折射率: 81.1604 cm^3
• 极化性: 32.167484 Å^3
• 极化表面积: 55.84 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Ethanol; Water
• 外观: White Solid
• 熔点: 187-1890C
• 闪点: 11 °C; 51.8 °F

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: YM3050000
• 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; 1544
• 德国WGK号: 1; 2; 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 2; 3
• 危险公开号: 11-23/24/25-39/23/24/25; 60-25-43
• 安全公开号: 16-36/37-45; 53-22-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H301-H311-H331-H370; H301-H317-H360
• GHS警示性声明: P201-P280-P301 + P310-P308 + P313; P210-P260-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2; UN 1544 6.1/PG 3
• 毒品管制信息: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; USDEA Schedule II; Home Office Schedule 2; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.5% (HPLC)
• 浓度: ~1 mg/mL in methanol; 1.0 mg/mL±5% in methanol
• 级别: analytical standard, for drug analysis
• 杂质: ~1.2 mL solution
• 有效期: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C17H21NO4 · HCl

详细说明

Sigma Aldrich - C5776

Biochem/physiol Actions
分别以大约 300nM、900nM 和 400nM 的 Kis 抑制多巴胺、去甲肾上腺素和 5-羟色胺转运蛋白。不同于苯异丙胺，它不会影响儿茶酚胺的释放。

Sigma Aldrich - 19330

包装
安瓿瓶，含 1.2mL 溶液。

Sigma Aldrich - 51621

Biochem/physiol Actions
分别以大约 300nM、900nM 和 400nM 的 Kis 抑制多巴胺、去甲肾上腺素和 5-羟色胺转运蛋白。不同于苯异丙胺，它不会影响儿茶酚胺的释放。

Toronto Research Chemicals - C633500

Inhibits the dopamine, norepinephrine, and serotonin transporters. Unlike amphetamines, it has no effect on catecholamine release. Controlled substance. Anesthetic (local).

参考文献

• Blakely, R.D., et al.: Curr. Opin. Neurobiol., 10, 328 (2000)
• Cowell, R. M., et al.: Eur. J. Pharmacol., 389, 59 (2000)
• Fleckenstein, A.E., Eur. J. Pharmacol., 406, 1 (2000)
• Torres, G.E., et al.: Nat. Rev. Neurosci., 4, 13 (2000)