Diacetylmorphine

Title: Diacetylmorphine
CAS Registry Number: 561-27-3
CAS Name: (5a,6a)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)
Additional Names: heroin; diamorphine; acetomorphine
Molecular Formula: C21H23NO5
Molecular Weight: 369.41
Percent Composition: C 68.28%, H 6.28%, N 3.79%, O 21.66%
Literature References: Narcotic analgesic prepared from morphine and acetic anhydride: O. Hesse, Ann. 220, 203 (1883); from morphine and acetyl chloride: Small, Lutz, Chemistry of the Opium Alkaloids, Supplement No. 103, Public Health Reports, Washington (1932); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954). Comparison with acetylmorphine: N. B. Eddy, H. A. Howes, J. Pharmacol. Exp. Ther. 53, 430 (1935). Pharmacodynamics: J. G. Umans, C. E. Inturrisi, ibid. 218, 409 (1981). Toxicity: eidem, Eur. J. Pharmacol. 85, 317 (1982). Vapor pressure studies: A. H. Lawrence et al., Can. J. Chem. 42, 1886 (1984). Comprehensive description: D. K. Wyatt, L. T. Grady, Anal. Profiles Drug Subs. 10, 357-403 (1981).
Properties: Orthorhombic plates, tablets from ethyl acetate. mp 173°. bp12 272-274°. [a]D25 -166° (c = 1.49 in methanol). One gram dissolves in 1.5 ml chloroform, 31 ml alcohol, 100 ml ether, 1700 ml water. Slightly sol in ammonia or sodium carbonate soln, sol in alkalies, dec by boiling with water. Turns pink and emits acetic odor on prolonged exposure to air. LD50 i.v. in mice: 59 mmol/kg (Umans, Inturrisi).
Melting point: mp 173°
Boiling point: bp12 272-274°
Optical Rotation: [a]D25 -166° (c = 1.49 in methanol)
Toxicity data: LD50 i.v. in mice: 59 mmol/kg (Umans, Inturrisi)
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C21H23NO5.HCl.H2O
Molecular Weight: 423.89
Percent Composition: C 59.50%, H 6.18%, N 3.30%, O 22.65%, Cl 8.36%
Properties: Fine crystals, mp 243-244°. [a]D24 -156° (c = 1.044). Sol in 2 parts water, 11 parts alcohol. Insol in ether.
Melting point: mp 243-244°
Optical Rotation: [a]D24 -156° (c = 1.044)
Derivative Type: Methyl iodide
Molecular Formula: C21H23NO5.CH3I
Molecular Weight: 511.35
Percent Composition: C 51.67%, H 5.12%, N 2.74%, O 15.64%, I 24.82%
Properties: Needles, mp 252°, [a]D15 -107° (c = 0.896).
Melting point: mp 252°
Optical Rotation: [a]D15 -107° (c = 0.896)
NOTE: "China White" has been used as a term for very pure Southeast Asian heroin. This term has also been erroneously used to refer to 3-methylfentanyl and a-methylfentanyl, q.v., which are potent derivs of fentanyl, q.v. See: S. Stinson, Chem. Eng. News 59, 71 (Jan. 19, 1981).
NOTE: This is a controlled substance (opium derivative): 21 CFR, 1308.11.
Diafenthiuron Dialifor Diallate Diallyl Trisulfide Diallylamine

Heroin
Heroin - Heroine.svg
Heroin3Dan.gif
Systematic (IUPAC) name
(5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate
Clinical data
AHFS/Drugs.com entry
Pregnancy cat. Not yet classified, but studies have shown a risk of abnormalities, hepatitis, malnutrition, and many other effects.[1]
Legal status Prohibited (S9) (AU)
Schedule I (CA)
Class A (UK)
Schedule I (US)
Dependence liability High
Routes Inhalation, Transmucosal, Intravenous, Oral, Intranasal, Rectal, Intramuscular
Pharmacokinetic data
Bioavailability <35% (oral), 44–61% (inhaled)[2]
Protein binding 0% (morphine metabolite 35%)
Metabolism hepatic
Half-life <10 minutes[3]
Excretion 90% renal as glucuronides, rest biliary
Identifiers
CAS number 561-27-3 YesY
ATC code N07BC06
PubChem CID 5462328
DrugBank DB01452
ChemSpider 4575379 YesY
UNII 8H672SHT8E YesY
ChEBI CHEBI:27808 YesY
ChEMBL CHEMBL459324 YesY
Synonyms Diamorphine, Diacetylmorphine, Acetomorphine, (Dual) Acetylated morphine, Morphine diacetate
Chemical data
Formula C21H23NO5 
Mol. mass 369.41 g/mol
 YesY (what is this?)  (verify)

Heroin (diacetylmorphine or morphine diacetate (INN)), also known as diamorphine (BAN), and colloquially as H, smack, horse, brown, black, tar, and other names,[4] is an opioid analgesic synthesized by C.R. Alder Wright in 1874 by adding two acetyl groups to the molecule morphine, found in the opium poppy. It is the 3,6-diacetyl ester of morphine. Heroin itself is an active drug, but it is also converted into morphine in the body.[5]

When used in medicine, it is referred to as diamorphine, and typically used to treat severe pain, such as that resulting from a heart attack or a severe injury. The white crystalline form considered "pure heroin" is usually the hydrochloride salt, diacetylmorphine hydrochloride. Bayer named the first diamorphine product Heroin; that name is now used primarily to describe illicit diacetylmorphine.

Illicit heroin is sometimes available in freebase form, dulling the sheen and consistency to a matte-white powder.[6] Because of its lower boiling point, the freebase form of heroin is also smokable. It is prevalent in heroin coming from Afghanistan, which as of 2004 produced roughly 87% of the world supply in illicit raw opium.[7] However, the production rate in Mexico has risen sixfold from 2007 to 2011, changing that percentage and placing Mexico as the second largest opium producer in the world.[8]

Mexican cartels are also known to produce a third type of illicit heroin, commonly called black tar, which results from a simplified, quicker synthesis procedure and contains a high percentage of morphine derivates other than heroin, such as 6-Monoacetylmorphine (6-MAM).

As with other opioids, diacetylmorphine is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence. Internationally, diacetylmorphine is controlled under Schedules I and IV of the Single Convention on Narcotic Drugs.[9] It is illegal to manufacture, possess, or sell diacetylmorphine without a license in almost every country.

Under the chemical names diamorphine and diacetylmorphine, heroin is a legally prescribed controlled drug in the United Kingdom, and is supplied in tablet or injectable form for the same indications as morphine is, often being preferred over morphine due to its lower side-effect profile.[citation needed] It is also available for prescription to long-term users as a form of opioid replacement therapy in the Netherlands, United Kingdom, Switzerland, Germany, and Denmark, alongside psycho-social care—in the same manner that methadone or Suboxone (buprenorphine) are used in the United States and Canada[10][11]—and a similar programme is being campaigned for by liberal political parties in Norway.