(1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18),15-tetraen-10-yl acetate

• ChemBase编号: 127670
• 分子式: C21H23NO5
• 平均质量: 369.41102
• 单一同位素质量: 369.15762284
• SMILES: CC(=O)Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1OC(=O)C)C
• Canonical SMILES: CC(=O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC(=O)C
• InChI: InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
• InChIKey: GVGLGOZIDCSQPN-PVHGPHFFSA-N

名称和登记号

名称

• IUPAC标准名: (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-10-yl acetate
• IUPAC传统名: (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-10-yl acetate
• 别名: 二乙酰吗啡; 海洛因; Heroin; Diamorphine; Diacetylmorphine; Acetomorphine; (Dual) Acetylated morphine; Morphine diacetate; Heroin

登记号

• CAS号: 561-27-3
• EC号: 209-217-7
• MDL号: MFCD00468072
• PubChem SID: 162221988; 24895466
• PubChem CID: 5462328
• CHEBI ID: 27808
• ATC码: N07BC06
• CHEMBL: 459324
• Chemspider ID: 4575379
• DrugBank ID: DB01452
• 美国药典/FDA物质标识码: 8H672SHT8E
• 维基百科标题: Heroin

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): -1.697644
• LogD (pH = 7.4): -0.152045
• Log P: 1.549009
• 摩尔折射率: 98.4254 cm^3
• 极化性: 38.45062 Å^3
• 极化表面积: 65.07 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.1 M HCl: <6.67 mg/mL; ethanol: soluble6 mg/mL; H2O: <0.2 mg/mL
• 外观: solid

安全信息

• 保存条件: desiccated
• RTECS编号: QC8050000
• 欧盟危险性物质标志: 剧毒(Highly 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): 1
• 危险公开号: 26/27/28
• 安全公开号: 22-36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P302 + P350
• 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
• RID/ADR: UN 1544 6.1/PG 1
• 毒品管制信息: USDEA Schedule I; 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: Inhalation, Transmucosal, Intravenous, Oral, Intranasal, Rectal, Intramuscular
• 生物利用度: <35% (oral), 44–61% (inhaled)
• 依赖倾向: High
• 排泄: 90% renal as glucuronides, rest biliary
• 半衰期: <10 minutes
• 代谢: hepatic
• 蛋白结合率: 0% (morphine metabolite 35%)
• 法定药品分级: Class A (UK); S9 (Australia); Schedule I (Canada); Schedule I (US)
• 妊娠期药物分类: Not yet classified, but studies have shown a risk of abnormalities, hepatitis, malnutrition, and many other effects.

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H23NO5