(1S,5R,13R,14S,17R)-10-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-yl acetate

• ChemBase编号: 1255
• 分子式: C21H23NO5
• 平均质量: 369.41102
• 单一同位素质量: 369.15762284
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(OC(=O)C)cc3)C=C[C@@H]2OC(=O)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)-10-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-yl acetate
• IUPAC传统名: heroin
• 别名: diacetylmorphine; diamorphine; Smack; Heroin

登记号

• CAS号: 561-27-3
• PubChem SID: 160964715; 46506839
• PubChem CID: 5462328

理论计算性质

JChem

• 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

ALOGPS 2.1

• Log P: 2.3
• LOG S: -3.14
• 溶解度: 2.66e-01 g/l

分子性质

理化性质

• 溶解度: 0.6 mg/mL at 25 oC [SEIDELL,A (1941)]
• 疏水性(logP): 1.58 [AVDEEF,A ET AL. (1996)]

详细说明

DrugBank - DB01452

• Drug Groups: illicit; experimental
• Description: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed) Internationally, heroin is controlled under Schedules I and IV of the Single Convention on Narcotic Drugs. It is illegal to manufacture, possess, or sell heroin in the United States and the UK. However, under the name diamorphine, heroin is a legal prescription drug in the United Kingdom.
• Indication: Used in the treatment of acute pain, myocardial infarction, acute pulmonary oedema, and chronic pain.
• Pharmacology: The onset of heroin's effects is dependent on the method of administration. Taken orally, heroin is totally metabolized in vivo into morphine before crossing the blood-brain barrier; so the effects are the same as oral morphine. Take by injection, heroin crosses into the brain. Once in the brain, heroin is rapidly metabolized into morphine by removal of the acetyl groups, therefore, it is known as a prodrug. It is the morphine molecule that then binds with opioid receptors and produces the subjective effects of the heroin high.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Bioavailability is less than 35%.
• Half Life: 2-3 hours
• Protein Binding: 0% (morphine metabolite 35%)
• Elimination: 90% renal as glucuronides, rest biliary
• References: Tschacher W, Haemmig R, Jacobshagen N: Time series modeling of heroin and morphine drug action. Psychopharmacology (Berl). 2003 Jan;165(2):188-93. Epub 2002 Oct 29. [Pubmed]
• External Links: Wikipedia; Drugs.com

参考文献

• Tschacher W, Haemmig R, Jacobshagen N: Time series modeling of heroin and morphine drug action. Psychopharmacology (Berl). 2003 Jan;165(2):188-93. Epub 2002 Oct 29. Pubmed