O-Acetyldihydrocodeine hydrochloride

R05DA12(WHO) AU:S8 (Controlled)BR:Class A2(Narcotic drugs)CA:Schedule IDE:Anlage I(Authorized scientific use only)UK:Class BUS:Schedule I 3-methoxy-6-acetoxy-(5α,6α)-4,5-epoxy-17-methylmorphinan 3861-72-1Y 5463874 DB01538Y 4576412Y SGY1T84P34 DTXSID30191930 Interactive image 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/s1NKey:LGGDXXJAGWBUSL-BKRJIHRRSA-NN Acetyldihydrocodeineis anopiatederivative discovered in Germany in 1914and 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 ofdihydrocodeineand is metabolised in the liver by demethylation and deacetylation to producedihydromorphine. Since acetyldihydrocodeine has higherlipophilicitythancodeineand is converted into dihydromorphine rather thanmorphine, it can be expected to be more potent and longer-lasting. It also has a higherbioavailabilitythan codeine. Side effects are similar to those of otheropiatesand includeitching,nauseaandrespiratory 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.