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Azidomorphine
Sign in to saveAzidomorphine is an opiate analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.
Chemical data
- Formula
- C17H20N4O2
- Molecular weight
- 312.37 g/mol
- IUPAC name
- (4R,4aR,7R,7aR,12bS)-7-azido-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
- SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@@H](CC4)N=[N+]=[N-]
- InChIKey
- KZOKOEQTKWBKOK-XHQKLZHNSA-N
- XLogP
- 3.4
- Polar surface area
- 47.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 312.158626
Show 4 more facts
- Commons category
- Azidomorphine
- chemical formula
- C₁₇H₂₀N₄O₂
- canonical SMILES
- CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)N=[N+]=[N-]
- isomeric SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@@H](CC4)N=[N+]=[N-]
Sources (2)
via Wikidata · CC0
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Encyclopedic overview
1 sectionsContents
- References
Azidomorphine is an opiate analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.
Azidomorphine binds with high affinity to the mu opioid receptor, and is around 40× more potent than morphine in vivo. It has similar effects to morphine, including analgesia, sedation, and respiratory depression. However, its addiction liability has been found to be slightly lower than that of morphine in animal studies.
Excerpted from Wikipedia’s “Azidomorphine” article, available under the CC BY-SA 4.0 licence.