Acetyldihydrocodeine

Opioid analgesic and cough suppressant drug

R05DA12 (WHO)

Legal statusLegal status

AU: S8 (Controlled)
BR: Class A2 (Narcotic drugs)^[1]
CA: Schedule I
DE: Anlage I (Authorized scientific use only)
UK: Class B
US: Schedule I

Identifiers

IUPAC name

3-methoxy-6-acetoxy-(5α,6α)-4,5-epoxy-17-methylmorphinan

CAS Number

3861-72-1^Y

PubChem CID

5463874

DrugBank

DB01538^Y

ChemSpider

4576412^Y

UNII

SGY1T84P34

CompTox Dashboard (EPA)

DTXSID30191930

ECHA InfoCard100.021.253

Chemical and physical dataFormulaC₂₀H₂₅NO₄Molar mass343.423 g·mol⁻¹3D model (JSmol)

Interactive image

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^N
Key:LGGDXXJAGWBUSL-BKRJIHRRSA-N^N

^NY (what is this?) (verify)

Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914^[2] 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 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. It also has a 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

^ 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. Retrieved 2023-08-03.
^ von Braun J (1914). "Untersuchungen über Morphium-Alkaloide". Chemische Berichte. 47 (2): 2312–2330. doi:10.1002/cber.191404702149.

Cough and cold preparations (R05)

Expectorants

Althea root
Ammonium Chloride
Antimony pentasulfide
Cineole
Creosote
Guaiacolsulfonate
Guaifenesin (+codeine, +hydrocodone, +oxomemazine)
Hederae helicis folium
Ipecacuanha (Syrup of ipecac)
Levoverbenone
Potassium iodide
Senega
Tyloxapol

Mucolytics

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine Benzylmorphine Butorphanol Codeine^# (+guaifenesin) Dextromethorphan Dihydrocodeine Dimemorfan Ethylmorphine Heroin Hydrocodone (+guaifenesin, +homatropine) Hydromorphone Laudanum Levomethadone Levopropoxyphene Methadone Nicocodeine Nicodicodeine Normethadone Noscapine Pholcodine Thebacon
Other	Alloclamide Benproperine Benzonatate Bibenzonium bromide Butamirate Clobutinol Clofedanol Cloperastine Dibunate Dimethoxanate Diphenhydramine Dropropizine Droxypropine Fedrilate Fominoben Gefapixant Glaucine Isoaminile Levodropropizine Meprotixol Moguisteine Morclofone Nepinalone Oxeladin Oxolamine Pentoxyverine Pipazetate Piperidione Prenoxdiazine Tipepidine Zipeprol

Opium alkaloids,
opioids,
and derivatives