Few questions regarding H

Discussion in 'Drug Chemistry' started by TokeTrip, Mar 29, 2011.

  1. TokeTrip

    TokeTrip Senior Member

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    Would acetyl codeine, reacted with Pyridine HCl, be a reasonable way to achieve 6-MAM?

    Would it be more productive to acetylate codeine, catalytically hydrogenate to 6-acetyl-dihydrocodeine, and then demethylate with HBr, or would that knock off the 6-acetyl group in addition to the 3-methoxy group? And would the aforesaid, using pyridine HCl for demethylation, also break the 6-acetyl group in addition to the 3-methoxy group? If I remember dihydrocodeine can be demethylated with HBr safely without breaking the ether bridge from 4-5.

    Would oxycodone/morphone be more potent with an acetyl group at the 6 position instead of a double bonded oxygen?

    Would oxymorphone/codone(9-hydroxymorphone, right?) reacted with thionyl chloride still go from 9-hydroxymophone/codone to 9-hydroxy-6-chloromorphide/codide? Like an oxychloromorphide? Where it's essentially oxymorphone/codone with a chlorine instead of the oxygen at the 6 position?

    If one had hydromorphone, would acetylating it using acetic anhydride still place a acetyl group at the 6- position, instead of the oxygen double bonded?

    And finally, does anybody know if 6-acetyl-oxycodeine is toxic, like acetylcodeine is?
     

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