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Acetyldihydrocodeine

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Opioid analgesic and cough suppressant drug
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Pharmaceutical compound
Acetyldihydrocodeine
Clinical data
Other namesAcetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
Identifiers
  • 3-methoxy-6-acetoxy-(5α,6α)-4,5-epoxy-17-methylmorphinan
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.021.253Edit this at Wikidata
Chemical and physical data
FormulaC20H25NO4
Molar mass343.423 g·mol−1
3D model (JSmol)
  • O=C(O[C@@H]4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@H]3CC4)C)C
  • 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 ☒N
  • Key:LGGDXXJAGWBUSL-BKRJIHRRSA-N ☒N
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Acetyldihydrocodeine is anopiate derivative discovered in Germany in 1914[2] and was used as a cough suppressant andanalgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative ofthebacon, where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative ofdihydrocodeine and is metabolised in the liver by demethylation and deacetylation to producedihydromorphine.

Since acetyldihydrocodeine has higherlipophilicity thancodeine and is converted into dihydromorphine rather thanmorphine, it can be expected to be more potent and longer-lasting. It also has a higherbioavailability than codeine. Side effects are similar to those of otheropiates and includeitching,nausea andrespiratory 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

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-03.
  2. ^von Braun J (1914)."Untersuchungen über Morphium-Alkaloide".Chemische Berichte.47 (2):2312–2330.doi:10.1002/cber.191404702149.
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