Acetyldihydrocodeine

Acetyldihydrocodeine

Systematic (IUPAC) name
3-methoxy-6-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
CAS Number	3861-72-1
ATC code	R05DA12 (WHO)
PubChem	CID 5463874
DrugBank	DB01538
ChemSpider	4576412
UNII	SGY1T84P34
Synonyms	Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
Chemical data
Formula	C20H25NO4
Molar mass	343.417 g/mol
SMILES O=C(O[C@@H]4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@H]3CC4)C)C
InChI InChI=1S/C20H25NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6,13-14,16,19H,5,7-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1 Key:LGGDXXJAGWBUSL-BKRJIHRRSA-N
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Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914^[1] 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 double 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, 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 elsewhere 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.

References

1. v. Braun, J. (1914). "Untersuchungen über Morphium-Alkaloide". Chemische Berichte 47 (2): 2312–2330. doi:10.1002/cber.191404702149.