Acetyldihydrocodeine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Acetyldihydrocodeine
Acetyldihydrocodeine.svg
Acetyldihydrocodeine ball-and-stick.png
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 Schedule I (US)
Identifiers
CAS number 3861-72-1 N
ATC code R05DA12
PubChem CID 5463874
DrugBank DB01538
ChemSpider 4576412 N
UNII SGY1T84P34 YesY
Synonyms Acetyldihydrocodeine, Dihydrothebacone, 6-acetyl-7,8-dihydrocodeine
Chemical data
Formula C20H25NO4 
Mol. mass 343.417 g/mol
 N (what is this?)  (verify)

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 derivat 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. The 2013 annual production quota from the DEA is 2 grammes.

References[edit]

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