Acetyldihydrocodeine

drugbox
IUPAC_name = 3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan

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width = 200
CAS_number = 3861-72-1
synonyms = Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
ATC_prefix = R05
ATC_suffix = DA12
PubChem = 5463874
smiles = C12=CC=C(C5=C1 [C@@] 34 [C@H] (C(C2)N(C)CC3)CC [C@@H] ( [C@@H] 4O5)OC(C)=O)OC
DrugBank =
C = 20 | H = 25 | N = 1 | O = 4
molecular_weight = 343.417 g/mol
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Acetyldihydrocodeine is an opiate derivative developed in Germany around 1900 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. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression.

Although an opioid of low to moderate strength and use in medicine elswehere in the world, acetyldihydrocodeine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9051 and the one salt in use, acetyldihydrocodeine hydrochloride, has a freebase conversion ratio of 0.90.