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
1. Chan YY, Yang SN, Lin JC, Chang JL, Lin JG, Lo WY. (2015)
Inflammatory response in heroin addicts undergoing methadone maintenance treatment.
Psychiatry Res, 226 (1): 230-4. [PMID:25660662]
2. Darke S, Duflou J. (2016)
The toxicology of heroin-related death: estimating survival times.
Addiction, 111 (9): 1607-13. [PMID:27082514]
3. Piepenbrink MS, Samuel M, Zheng B, Carter B, Fucile C, Bunce C, Kiebala M, Khan AA, Thakar J, Maggirwar SB et al.. (2016)
Humoral Dysregulation Associated with Increased Systemic Inflammation among Injection Heroin Users.
PLoS ONE, 11 (7): e0158641. [PMID:27379802]