diamorphine   Click here for help

GtoPdb Ligand ID: 9082

Synonyms: acetomorphine | diacetylmorphine | heroin
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Diamorphine (heroin) is a morphine derivative. It acts as a potent opioid receptor agonist after deacetylation to 6-acetylmorphine and subsequently to morphine [2].
Internationally, heroin is a controlled narcotic drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 65.07
Molecular weight 369.16
XLogP 1.42
No. Lipinski's rules broken 0
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Canonical SMILES CC(=O)OC1C=CC2C34C1Oc1c4c(CC2N(CC3)C)ccc1OC(=O)C
Isomeric 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
No information available.
Summary of Clinical Use Click here for help
Under the name diamorphine, heroin is a legal prescription drug in the United Kingdom. May be used for the treatment of severe pain associated with surgical procedures, myocardial infarction or pain in the terminally ill and for the relief of dyspnoea in acute pulmonary oedema. Diamorphine may be given by the intramuscular, intravenous, subcutaneous or oral routes. A nasal spray formulation is available for use in children for treatment of acute severe nociceptive pain within a hospital setting.