Transacetylation of morphine

[joho]

Can someone please clarify in simple terms what this is? I.e is it the acetate group from 3position of diamorphine acetylating the 6-hydroxy position of morphine, producing diamorphine. Or is it 6-MAM and morphine producing 3-MAM? Or is it something else completely?

 

Help much appreciated as it is part of my revision and I have never quite got to the bottom of it!

[Mercedes Benzene]

The acetylation of morphine involves the addition of an acetyl group in place of the hydrogens in the diol group of the morphine molecule.

 

So, you start with two hydroxys, and end up with two acetyls.

Graphically:

 

[ce]-OH[/ce] and

[ce]-OH[/ce]

 

are transformed to:

 

[ce]O-COCH3[/ce] and

[ce]O-COCH3[/ce]

 

 

I hope that answers your question.

[joho]

Thankyou Mercedes Benzene. It was more whether the acetyl group came from 6-MAM or 3-MAM or diamorphine? Because I had found a definition which said the acetyl came from 6-MAM, onto the morphine to produce 3-MAM, but another definition said the acetyl group came from diamorphine and produced more diamorphine (which doesn't sound right!). Maybe it just doesn't matter, or maybe it comes from various places.

 

As it is for an exam I think I will be lucky to remember the simplest of definitions! Thanks anyway.

 

Edit: realised that I probably should have added that it was transacetylation whilst using methanol as a solvent for GC analysis!