Talk:Acetylpropionylmorphine

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Note that this compound has two possible isomers, either 3-acetyl-6-propionyl or 3-propionyl-6-acetyl, and neither the UNODC report or the couple of textbooks in which I've seen this compound referred to specify which isomer is the correct one. However the 3-acetyl-6-propionyl makes more sense from both a chemical and pharmacological standpoint. Firstly with the more easily hydrolysed acetyl group on the 3-position it will be the more active isomer, but more importantly in order to produce the compound without containing any traces of heroin (essential in order for the compound to be used as a legal alternative to heroin) it would have to be made by a two-step sequential acylation, as a one-pot reaction using acetic and propanoic anhydrides would result in a mix of heroin, dipropanoylmorphine and both isomers of acetylpropionylmorphine. Since monoacylation of morphine favours the 6-position and invariably results in some diacylated product if no protecting group is used, the reaction sequence morphine --> 6-propionylmorphine --> 3-acetyl-6-propionylmorphine is most likely, as only dipropionylmorphine will be present as a significant contaminant with virtually no heroin impurities produced.Meodipt (talk) 23:28, 28 January 2010 (UTC)[reply]