[jaysawatzki]

I am going to be honest here, I don't know much beyond a beginning level org chem. Actually very beginning, I know how to do attacking groups etc, but that is about it. However I do have a rather extensive neuroscience and medicinal chemistry background. Anyway I am going to cut to the chase and not bore you with the details of why the acetyl version would be much more effective than the hydroxy but it is true. (Just look at diacetylmorphine to the likes of codeine.) However if the PhD's ( ) around here would be nice enough to take a peek at the structure (below) and see if it is possible to replace the hydroxy group with an acetyl group I would be much obliged. (For the record here I am 16, not looking to use this for myself but I work with Pfizer occasionally and have been working with their Medicinal Chemists here and there, I am just a little embarrassed to ask for such beginner information when they think I am some 16 year old genius, (ha ha))

Thanks again

[sjb]

Well, I don't have a Ph.D., so take my opinion with a pinch of salt, but I can't see any real reason why not. It may not be as simple as taking 7-Hydroxymitragynine and treating it with classical acylating reagents, as I think the azadecalin and enol ether may interfere.

[sjb]

You might also want to have a look at http://dx.doi.org/10.1021%2Fjm010576e (J. Med. Chem., 2002, 45, 1949) which seems to suggest contrary to your expectations.

[jaysawatzki]

Interesting study, I have seen it before. But thanks. Up until recently the main alkaloid was thought to be mitragynine, however recent studies have shown that the mu receptor was activated by 7-hydroxymitragynine. I still stand by my reasoning why the acetyl group would function better in the body. But you never know until it's in trials.

Thanks for the input!

[jaysawatzki]

*Ignore me, I am impatient* for anyone reading to input. Anyone know if it is possible to replace that group?

Thanks for any input what so ever

[limpet chicken]

The 7-acetoxy derivative of mitragynine is commercially available, but, although it is per-weight unit, more potent than mitragynine and.or 7-OH mitragynine itself, it does seem subjectively less satisfying, having done a bioassay on both materials, there seems to be something 'missing', I can't quantify it in words, but subjectively, it does not feel as good.

For both pain (I have a broken-off shard of bone floating around in my knee joint from a childhood fight and an accident) and for relaxation, I definately find that out of mitragynine, the hydroxylated, and the acetoxy derivative, the hydroxy substitution was preferable.

The full spectrum alkaloid extract rather than the pure compound though is more effective by far in my opinion, theres quite the mix of different indole alkaloids in Mitragyna Speciosa, mitragynine derivatives being responsible for the mu receptor agonism (I think its a partial agonist btw), there are adrenoreceptor ligands that act like yohimbine, but these comprise a fairly small quantity of the total alkaloidal profile, and, most interestingly, in kratom (M.Speciosa) that has been improperly stored/aged, a compound called mitragynine pseudoxindole forms, which is a delta selective agonist, which I am inclined to think, would boost the effective antinociceptive action of kratom quite some, as delta opioid receptors are involved in mediation of pain at the spinal level.

Not, mind you, that I have done a side-by-side comparison of old, mangy kratom and fresh stuff, although once I get enough money to afford some plants, I intend to do exactly that

[jaysawatzki]

Great post. I completely spaced that acetoxy is the same as an acetyl group replacing the hydrogen. I have read that the pain-reducing effects of acetoxymitragynine are less than the hydroxymitragynine. Thanks for the clarification.