Heroin
[(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
Molecular Identity
Heroin
[(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
PubChem CID: 5462328
Heroin is a 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. It has a role as an opioid analgesic, a prodrug and a mu-opioid receptor agonist. It is functionally related to a morphine.
2D Structure
Properties
C21H23NO5
Molecular Formula
369.40
Molecular Weight
g/mol
369.1576
Exact Mass
Da
1.5
XLogP
Drug-like (Lipinski: < 5)
65.1
TPSA
Good oral absorption (< 140 A²)
0
H-Bond Donors
6
H-Bond Acceptors
692
Complexity
SMILES
Canonical SMILES
SMILES: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC(=O)C)CCN3CIsomeric SMILES
SMILES: CC(=O)O[C@H]1C=C[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)OC(=O)C)CCN3CSynonyms(20)
HEROINDiacetylmorphineDiamorphineAcetomorphine3,6-DiacetylmorphineMorphacetinDiaphormEclorionO,O'-DiacetylmorphineMorphine diacetateAcetomorfineDiacetylmorfinDiamorfinaDiasetilmorfinDiacephin
Data from PubChem (NCBI)
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