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Is there a practical way to change 4-ACO-DMT into 4-HO-DMT (psilocin) for ingestion?

mmm i wondered this too

i google'd it a while ago and someone on another forum had asked, and someone with the knowhow said "it's not the kind of thing you can just do in a bathtub" but i don't really know chemistry, so there *could* be an easy way out there

from what i've read, back before vendors started selling the more stable 'fumarate' version, the 4-aco-dmt use to just rapidly degrade into psilocin through oxidation. but for this same reason many stopped this practice to escape the illegal catchment area
 
Boil it with citric acid or vinegar for half an hour.

The conversion also happens pretty rapidly in your stomach and blood.
 
As an ester, 4-AcO-DMT should easily hydrolyze back into the parent alcohol (4-HO-DMT) and carboxylic acid (acetic acid) through either acid or base pathway.

Base hydrolysis is irreversible, as the carboxylic acid forms a salt with the base (say you used NaOH, then acetic acid is captured as sodium acetate), and faster reaction usually, but 4-HO-DMT is probably unstable under base conditions, so perhaps the acid pathway would be better. Gentle heating and mixing with aqueous acetic acid (vinegar would probably do) would probably be the best way to go about this. Boiling would probably destroy the 4-HO-DMT. Too bad, since it's likely to cause a much more complete hydrolysis.
 
Just curious, what would be the benefit in doing this? (all this time I thought I was supposed to try to prevent this from happening! lol )

And if this conversion does happen in the stomach anyway, does it not happen when 4-AcO-DMT is plugged?
 
The benefit is an apparently faster onset. I am doubtful there is any actual difference between 4-HO-DMT, 4-PO-DMT and 4-AcO-DMT when orally administered w.r.t the same dose of "psilocin base".

4-AcO-DMT would be expected to rapidly degrade in blood (to 4-HO-DMT) due to the presence of plasma esterase enzymes if administered IR, snorted, or IV.
 
And if this conversion does happen in the stomach anyway, does it not happen when 4-AcO-DMT is plugged?
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To my knowledge, it does, albeit at a bit lower rate.

Just curious, what would be the benefit in doing this?
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It's the benifit from tasting pure psilocin. Isn't it nice to try a new drug? :) And isn't it nice to try pure psilocin?
More pragmatic reason: you may feel it different from 4-AcO-DMT. Even if most people find 4-AcO- and 4-HO- tryptamines indistinguishable, others say they are quite different. And you don't know what part of people you belong to, until you tasted both.
 
I have little chemistry knowledge, so I have a few questions.

Do you need 4-ACO-DMT freebase in order for this to work or will the fumarate work as well?
If fumarate does work, would the resulting psilocin be 4-HO-DMT fumarate or would it change to freebase?
Someone on another thread said that using HCL for the hydrolysis would be the best. Would you agree?
 
Theoretically you'd want the irreversible base-catalyzed ester hydrolysis, because you need to neutralize the pH to be able to ingest it. If the reaction with an acid is reversible, then you could end up with a part of the acetate back on. Then again I am not sure at what rate they would associate again, especially if you dilute. Anyone?

It shouldn't matter what form of the drug you have, with base catalysis the fumarate will form a tiny little buffer just like it can with the cleaved acetate.

I am not sure what kind of psilocin acidification yields, quaternary cationic?
Doesn't really matter.

I have no practical experience with this method but I have certainly considered it especially since I recently got to know synthetic psilocin and found it special.

So personally I would just use lye, give it some time or TLC if I can, then neutralize again with HCl.

But - as always - you'd better wait for a second opinion.
 
It makes no sense to hydrolyze the aco group if you plan oral ingestion. You have enzymes all over the body that will do that for you -- even skipping pass 1 metabolisms like plugging IV IM or Intranasal.

Psilocin quaternary salts, btw, form best with small strong acids (HCl is really all we have, but that poor 4 group is so unprotected). Pretty unstable depending on the solvent and provided there's no trace nucleophiles, we can't even identify the substance yet. I am curious about a multiple charged acid salt like succinic acid that could stabilize the 4 positions.

My opinon which as poster #3 may mean very little: You're going to lose product on a procedure that accomplishes basically, nothing, but it will increase purity, even if by a very small amount. At best, you lose 5% of your compound, and at worst, you lose whatever traditional risks associated with RCs are.. It's been said too many times on this forum so I won't beat a dead horse.

Solipsis: psilocin as a quaternary salt -- counter ion? I'd be curious about some of the multi valent acids like succinic acid (just as an example) to see if their could be a stabilizing effect between the substances.

You'd need to do some fair amount of qualitative and quantitative analysis if you hope to accomplish what you're describing. I'd be curious to see if it makes a difference, but I don't see how it would, but everyone's MMV.
 
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I'm just going to chime in and say that I can't tell the difference between 4-AcO-DMT fumarate and 4-HO-DMT base. Even the time of onset seems identical. On the other hand, I'm sure Solipsis has more experience than I with both, so maybe there is a subtle difference.
 
I've never tried synthetic 4-ho-dmt, but I think there's a huge difference between 4-aco-dmt and mushrooms. I wastly prefer the later.

I personally believe that both 4-po-dmt, 4-aco-dmt and 4-ho-dmt each have their own distinct pharmacological action.

it would be insanely cool if there was some way for a kitchen chemist to turn 4-aco-dmt into 4-ho-dmt. I have 2 spare grams of 4-aco-dmt freebase I don`t mind experimenting with it if some one has a serious suggestion a method.

Solipsis said:
So personally I would just use lye, give it some time or TLC if I can, then neutralize again with HCl.
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What is TLC? Also, what PH would you aim for? 5?
 
Thin-layer chromatography? Maybe, unless it actually means tender loving care? Not sure which one in this case, stoned acronym ambiguity much...

I'm not great with chromatography, but I'd assume that would allow you to determine the relative amounts of the hydroxy and acetoxy esters, can't give better detail cause I don't know specifically what elutant would be called for.
 
Clarke's suggests psilocin is not stable in basic media, I would use an acid hydrolysis rather than a basic one to avoid turning your 4-ho-dmt into a blue quinoid goo

If the reaction with an acid is reversible, then you could end up with a part of the acetate back on. Then again I am not sure at what rate they would associate again, especially if you dilute. Anyone?
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Fischer esterification is reversible, but in aqueous solution the equilibrium favours the acid plus alcohol. Normally if you want to form the ester you have to drive water off the reaction somehow, to drive the reaction according to Le Chatelier's principle.

Another option is to just get a phosphatase enzyme (spit, blood?) and use that. Apparently, in the course of psilocin extraction from shrooms, enzymatic degradation of psilocybin was noted.
Additionally, a high activity of enzymes of the phosphatase type could be detected in these aqueous solutions from all species. In contrast to these results only the extracts of P. cubensis and P. cyanescens showed a significant enzymatic activity by using acetic acid as solvent. In these cases psilocybin was completely dephosphorylated to psilocin by heating the acid extracts and no baeocystin could be detected in P. cyanescens.
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http://www.erowid.org/plants/mushrooms/mushrooms_journal1.shtml
 
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sekio said:
Clarke's suggests psilocin is not stable in basic media, I would use an acid hydrolysis rather than a basic one to avoid turning your 4-ho-dmt into a blue quinoid goo



Fischer esterification is reversible, but in aqueous solution the equilibrium favours the acid plus alcohol. Normally if you want to form the ester you have to drive water off the reaction somehow, to drive the reaction according to Le Chatelier's principle.

Another option is to just get a phosphatase enzyme (spit, blood?) and use that. Apparently, in the course of psilocin extraction from shrooms, enzymatic degradation of psilocybin was noted.

http://www.erowid.org/plants/mushrooms/mushrooms_journal1.shtml
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Can you elaborate on that further? would one just get a sizeable amount of spit/blood in a container, put the 4-aco-dmt in there... and then do what? apply heat, leave it in for how long? I have no idea how any of this works but I have a big interest in converting my 4-aco-dmt into 4-ho if at all possible. If this is a stupid question just let me know, I have humility and don't mind :P
 
Years later I discover why my psilocin had a noticeable vinegar scent to it. I always ate them so I suppose it did not make much difference anyway.
Thanks for the information!
 
Seems to be the distinct impression in this thread that 4-AcO-DMT WILL be hydrolyzed in the body.
Is there really no difference between the two when ingested? Apologies for no input, all i've heard is the old 'acidify, heat and stir for a bit' but if my previous assertion is correct then they'll be indistinguishable anyway.
 
There's no definitive answer yet, certainly no scientific answer, and I don't think there are enough anecdotal comparisons made between actual psilocin and psilacetin to come to any sort of conclusion. And even if it hydrolizes in your body then that fact alone might account for a subjective difference (plus, the expectations one has between psilocin and 4-aco-dmt are different too)
 
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