I hear it is possible to "hydrolyze" 4-aco-dmt fumarate into 4-ho-dmt using either a base or an acid.....I hear of it being done with lye, but I hear 4-ho-dmt is somewhat unstable in a basic environment, so it is supposedly better to use an acid....someone I heard of used muriatic acid for this.....could acetic acid work?

Are they just blowing smoke? If one could turn 4-aco-dmt into psilocin, it would be fantastic.....4-aco-dmt feels very different from psilocin despite claims of it metabolizing into such in vivo.

Cant see why it wouldnt work with a base either as water is a stronger acid than the indole or alpha proton on the molecule so if the base (OH) did deprotonate them becoming H20 these stronger bases/weaker acids would immediately nab back their protons.


One potential problem though, is that ring with lone pairs nearby not strongly activating the ring? Actually its only a moderate activator.

Edit- in step six I think it would actually be a water molecule that is responsible for the deprotonation, that ring is damned resonace stabalized!

I don't science that hard....

I think thats more like it!

Well you started it!

So how would one go about doing this?

Ever heard of the lemon tek? This is basically the same idea.

I imagine any acid would probably work - acetic acid or citric acid should work. Given that 4-AcO is hypothesized to be metabolized into psilocin in the stomach (which is .5-1M HCl), that seems like a good place to start.

Blessings
~ND

Well firstly find someone more sure of himself than I am! Let’s just wait for someone more knowledgeable to chime in and we can discuss it further. I got an idea how you could do it but I'm not going to give any suggestions as it would be tantamount to giving unqualified medical advice! This is the first time I've even set eyes on this molecule!

I’ve been studying O-chem for a while but apart from DMT and mescaline extractions have no lab experience whatsoever! I’m not even sure if my proposed mechanism is correct, and was actually hoping for some disscussion and feedback!

This particular reaction I doubt very much would be all that dangerous but with chemistry you have to make damned sure that you know what you are doing as well all the side products that you might end up making or you could end up poisoning yourself!

And no you can’t just protonate it with acetic acid there would be no leaving gorup.

Maybe you can explain or provide a link as to what those who suggested this proposed as a mechanism. First time I've heard of it so I havent given it much thought.

Isnt the theroy behind the so called 'lemmon tek' supposed to say that it converts psilocybin into psilocin before ingestion?

Makes sense if you look at the two molecules and imagine what would happen if psilocybin was to undergo protonation.

The acetoxy group is used as a protecting group for alcohols - I did some more digging and found that deprotection can be both acid and base catalyzed, take a gander at this link:
http://www.synarchive.co...ng-group/Alcohol_Acetate

Glacial acetic acid has a pH of 2.4, which may be harsh enough, I'm really not sure. I'm not really feeling up for looking through a bunch of literature on protecting/deprotecting groups at 1am. I work with a chemist, so I can shoot them this question if we're still interested. If Benzyme wanted to chime in on the differences between dephosphorylation and deacetylation, they're the resident expert.

Here's the Nichols paper that first suggested that 4-AcO-DMT may be a prodrug of 4-HO-DMT
https://www.erowid.org/a...ols/nichols-psilocin.pdf

Blessings
~ND

Yeah like I said and showed with the mechanism above I believe it could work with either an acid or a base. That is OH or H30 but this would be different than just protonation with acetic acid.

If you protonate water (with H2SO4 for example) this will protonate the carbonyl and then the water will attack as a nucleophile, after a few deprtonation/protonation steps the alcohol or Oxygen group will then be forced out as a good leaving group. In this instance the OR group has to leave as a leaving group when the carbonyl tries to reform.

But I dont think it will just work if you only dumped a load of acetic acid in there, because all this would do is protonate the O group, and there would be no mechanism to drive the reaction onwards and expel the leaving group. The pictures I provided below should make this clearer. Let me know if I am missing something!

Any acid (acetic acid, HCl, etc) will also protonate water in an aqueous environment, providing the hydorium ions you need to deacetylate. I worked through your mechanism, and it looks pretty good to me, although I think you need to deprotonate the geminal diol in step five for the double bond to reform.

Blessings
~ND

http://www.chemguide.co.uk/phys...catalysis/hydrolyse.html

Glacial acetic acid won't work, of course. Hydrolysis always involves the reaction with water, the base or acid is only the catalyst.

Oops, my bad - that's true.

Blessings
~ND

So what do I do?

Research.

The articles describing the hydrolysis of psilocybin from mushroom bodies cannot be translated to your substance, because in those cases the hydrolysis is catalyzed by enzymes in the mushrooms. Your pure 4-AcO-DMT does not come with these enzymes, so that the hydrolysis will have to be catalyzed by the acetic acid alone.

Do not try base catalyzed hydrolysis, the hydrolyzed 4-HO-DMT does not like that and will quickly degrade if you try that. In fact the molecule is so fragile that you should take care to exclude oxygen out of the reaction as much as possible until the reaction solution has been cooled down and neutralized. Before adding the 4-AcO-DMT to the dilute acetic acid solution, it should be boiled for a few minutes to expel dissolved oxygen. If you can sparge the liquid with nitrogen or even run the hydrolysis reaction under a protective blanket of nitrogen, that would be best.

Alas, I have no quick answers for you. It is much easier to ask questions than to give sensible and useful answers. Implementing the answers is even harder.