(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 ID: 1255
• Molecular Formular: C21H23NO5
• Molecular Mass: 369.41102
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: heroin
• Synonyms: diacetylmorphine; diamorphine; Smack; Heroin

Database IDs

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

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.697644
• LogD (pH = 7.4): -0.152045
• Log P: 1.549009
• Molar Refractivity: 98.4254 cm^3
• Polarizability: 38.45062 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.3
• LOG S: -3.14
• Solubility (Water): 2.66e-01 g/l

PROPERTIES

Physical Property

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

DETAILS

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

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