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CHEBI:27808 - heroin

ChEBI IDCHEBI:27808
ChEBI Nameheroin
Stars
DefinitionA morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.
Secondary ChEBI IDsCHEBI:5680, CHEBI:24528
Last Modified22 February 2017
DownloadsMolfile
FormulaC21H23NO5
Net Charge0
Average Mass369.417
Monoisotopic Mass369.15762
SMILES[H][C@@]12C=C[C@H](OC(C)=O)[C@@H]3Oc4c(OC(C)=O)ccc5c4[C@@]31CCN(C)[C@@H]2C5
InChIInChI=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
InChIKeyGVGLGOZIDCSQPN-PVHGPHFFSA-N
Wikipedia
Roles Classification
Biological Roles:
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
heroin (CHEBI:27808) has functional parent morphine (CHEBI:17303)
heroin (CHEBI:27808) has role opioid analgesic (CHEBI:35482)
heroin (CHEBI:27808) has role prodrug (CHEBI:50266)
heroin (CHEBI:27808) has role μ-opioid receptor agonist (CHEBI:55322)
heroin (CHEBI:27808) is a morphinane alkaloid (CHEBI:25418)
IUPAC Name 
17-methyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diyl diacetate
Synonyms  Source
HeroinKEGG COMPOUND
DiacetylmorphineChemIDplus
3,6-DiacetylmorphineChemIDplus
7,8-Dihydro-4,5-alpha-epoxy-17-methylmorphinan-3,6-alpha-diol diacetateChemIDplus
O,O'-DiacetylmorphineChemIDplus
(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)NIST Chemistry WebBook
Manual XrefsDatabases
C06534KEGG COMPOUND
DB01452DrugBank
HeroinWikipedia
D07286KEGG DRUG
4412DrugCentral
Registry NumbersSources
Reaxys:99261Reaxys
CAS:561-27-3KEGG COMPOUND
CAS:561-27-3ChemIDplus
CAS:561-27-3NIST Chemistry WebBook
Citations