Structure via PubChem · Public domain (PubChem)
acetyldihydrocodeine
Sign in to saveAlso known as dihydrothebacone, dihydrocodeine 6-acetate
Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914 and was used as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of thebacon, where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of dihydrocodeine and is metabolised in the liver by demethylation and deacetylation to produce dihydromorphine.
Chemical data
- Formula
- C20H25NO4
- Molecular weight
- 343.4 g/mol
- IUPAC name
- [(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
via PubChem
Wikidata facts
- Mass
- 343.17835828
Show 5 more facts
- chemical formula
- C₂₀H₂₅NO₄
- Commons category
- Acetyldihydrocodeine
- isomeric SMILES
- CC(=O)O[C@H]1CC[C@H]2[C@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3C)OC
- canonical SMILES
- CC(=O)OC1CCC2C3CC4=C5C2(C1OC5=C(C=C4)OC)CCN3C
- defined daily dose
- 30
Sources (3)
via Wikidata · CC0
~1 min read
Article
1 sectionsContents
- References
Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914 and was used as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of thebacon, where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of dihydrocodeine and is metabolised in the liver by demethylation and deacetylation to produce dihydromorphine.
Since acetyldihydrocodeine has higher lipophilicity than codeine and is converted into dihydromorphine rather than morphine, it can be expected to be more potent and longer-lasting. It also has a higher bioavailability than codeine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression.