Diacetylmorphine

Heroin
INN: Diamorphine
Clinical data


Pronunciation	Heroin: /ˈhɛroʊɪn/
AHFS/Drugs.com	heroin
Dependence liability	Physical: Very high Psychological: Very high
Addiction liability	Highly
Routes of administration	Intravenous, inhalation, transmucosal, by mouth, intranasal, rectal, intramuscular, subcutaneous, intrathecal
Drug class	opiate
ATC code	N07BC06 (WHO)
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) NZ: Class A UK: Class A US: Schedule I UN: Narcotic Schedules I and IV
Pharmacokinetic data
Bioavailability	<35% (by mouth), 44–61% (inhaled)
Protein binding	0% (morphine metabolite 35%)
Metabolism	liver
Onset of action	Within minutes
Biological half-life	2–3 minutes
Duration of action	4 to 5 hours
Excretion	90% kidney as glucuronides, rest biliary
Identifiers
IUPAC name (5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate
Synonyms	Diamorphine, Diacetylmorphine, Acetomorphine, (Dual) Acetylated morphine, Morphine diacetate
CAS Number	561-27-3^Y
PubChem (CID)	5462328
DrugBank	DB01452^Y
ChemSpider	4575379^Y
UNII	8H672SHT8E^Y
ChEBI	CHEBI:27808^Y
ChEMBL	CHEMBL459324^Y
ECHA InfoCard	100.008.380
Chemical and physical data
Formula	C₂₁H₂₃NO₅
Molar mass	369.41 g/mol
3D model (Jmol)	Interactive image
SMILES CC(OC1=C(O[C@@H]2[C@]34CCN(C)[C@@H]([C@@H]4C=C[C@@H]2OC(C)=O)C5)C3=C5C=C1)=O
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^Y Key:GVGLGOZIDCSQPN-PVHGPHFFSA-N^Y

Heroin, also known as diamorphine among other names, is an opiate typically used as a recreational drug for its euphoric effects. Medically it is occasionally used to relieve pain and as a form of opioid replacement therapy alongside counseling. Heroin is typically injected, usually into a vein; however, it can also be smoked, snorted or inhaled. Onset of effects is usually rapid and lasts for a few hours.

Common side effects include respiratory depression (decreased breathing) and about a quarter of those who use heroin become physically dependent. Other side effects can include abscesses, infected heart valves, blood borne infections, constipation, and pneumonia. After a history of long-term use, withdrawal symptoms can begin within hours of last use. When given by injection into a vein, heroin has two to three times the effect as a similar dose of morphine. It typically comes as a white or brown powder.

Treatment of heroin addiction often includes behavioral therapy and medications. Medications used may include methadone or naltrexone. A heroin overdose may be treated with naloxone. An estimated 17 million people as of 2015 use opiates such as heroin, which together with opioids resulted in 122,000 deaths. The total number of opiate users has increased from 1998 to 2007 after which it has remained more or less stable. In the United States about 1.6 percent of people have used heroin at some point in time. When people die from overdosing on a drug, the drug is usually an opioid.

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