Acetyldihydrocodeine is an

opiate An opiate, in classical pharmacology, is a substance derived from opium. In more modern usage, the term ''opioid'' is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain (including antagonis ...

derivative discovered in Germany in 1914 and was used as a cough suppressant and

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of

Thebacon Thebacon (INN; pronounced ), or dihydrocodeinone enol acetate, is a semisynthetic opioid that is similar to hydrocodone and is most commonly synthesised from thebaine. Thebacon was invented in Germany in 1924, four years after the first synthe ...

, where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of

dihydrocodeine Dihydrocodeine is a semi-synthetic opioid analgesic prescribed for pain or severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) (as in co-dydramol) or aspirin. It was developed in Germany in 1908 a ...

and is metabolised in the liver by demethylation and deacetylation to produce

dihydromorphine Dihydromorphine (Paramorfan, Paramorphan) is a semi-synthetic opioid structurally related to and derived from morphine. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine.Rama Rao Nadendla. Principles Of Organic ...

. Since acetyldihydrocodeine has higher

lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...

than

codeine Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, ''Papaver somniferum''. It is typically use ...

and is converted into dihydromorphine rather than

morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make ...

, it can be expected to be more potent and longer-lasting. It also has a higher

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

than codeine. Side effects are similar to those of other

opiates An opiate, in classical pharmacology, is a substance derived from opium. In more modern usage, the term ''opioid'' is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain (including antagonist ...

and include

itching Itch (also known as pruritus) is a sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of sensory experience. Itch has many similarities to pain, and while both are unpleasan ...

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

and

respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapnia ...

. 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

Analgesics 4,5-Epoxymorphinans Catechol ethers Acetate esters Mu-opioid receptor agonists Semisynthetic opioids Cyclic ethers Heterocyclic compounds with 5 rings {{analgesic-stub