Thursday, October 18, 2007

Acetyldihydrocodeine

Systematic (IUPAC) name
3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan

Identifiers: CAS number 3861-72-1; ATC code R05DA12
PubChem 5463874.
Chemical data: Formula C20H25NO4; Mol. mass 343.417 g/mol; Synonyms Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine.

Acetyldihydrocodeine is an opiate derivative developed as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. 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, and also have higher bioavailability than codeine; however its action is still limited by the rate at which liver enzymes demethylate it into dihydromorphine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression.

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