Question about 3&6-monoacetylmorphine

[twgburst]

I have read a little about them and heard that they can be made with glacial AA and are 2x as potent as morphine. I also hear that these are sometimes present in street heroin. Anyone got any info or links that have info about these.

 

[fastandbulbous]

If heroin (3,6-diacetylmorphine) gets damp, it fairly quickly hydrolyses to 6-monoacetylmorphine, as an ester of a phenolic OH will hydrolyse much more quickly than the ester of an ordinary alcoholic OH group. the monoacetylmorphine is a bit more resistant to hydrolysis, but is closer to heroin than morphine, in terms of potency

 

[Riemann Zeta]

Don't attempt a synthesis of these compounds, it will not work (and, of course, could land you in prison for the next 20-30yrs). Acetic acid (or any other carboxylic acid) does not take kindly to nucleophilic attack, as a proton transfer always occurs first in the presence of a base, leaving a very non-electrophilic anion. The only way of doing add'n/elim reactions with acid moieties is to use a ridiculously strong base/nucleophile like MeLi.

 

[twgburst]

I wouldn't plan on trying anything of the sort without finishing orgo 1&2, also I wouldn't try it in the US with the way our drug laws work. This was out of curiosity.