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Conversion of 4-AcO- into 4-Ho Tryptamines

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willkell420

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I was reading in another thread where someone had tried to convert 4-aco-dmt to 4-ho-dmt by adding NaOH to a water solution of 4-aco-dmt. It was never determined in the thread whether or not it worked. Does anyone know of a way that this conversion could be done? Thanks.....
 
Ester hydrolysis can be acid or base catalysed. You've described base catalysis. You could also do this reaction with the addition of some sulfuric or phosphoric acid to the solution followed by heating.

I do not recommend you try either though, since 4-HO-DMT is unstable in solution and will probably degrade to inactive junk in the process of doing this.
 
matt could you elaborate on the instability, why is it more unstable than 4-ho-dmt under normal circumstances, is the solution changing color a sign that the conversion is complete?
 
If the solution changed color I would be concerned, psilocin (4-HO-DMT) as we know changes color to blue when it is degraded (so while your mushrooms turning blue is indeed indicative they have psilocin in them for example, the bluer they are, the more of it has degraded!), so if the solution changed color it probably means it's degrading.
At the same time though yes it will be indicating the reaction is working, because it it wasn't, there wouldn't be the molecules available for forming those coloured products.

As for why it is more unstable - most drugs are more unstable in solution, and especially amines! This is because when in solution a molecule is fully mobile and has much more opportunities to interact with other molecules (such as water if it is an aqueous solution!). Psilocin seems to be especially susceptible to degradation in aqueous solution - the 4 hydroxyl seems to be the reactive site. When it is blocked by the acetoxy reverse ester in 4-AcO-DMT, it's unreactive.
 
So is it possible to do this reaction without destroying most of the product? Has anyone done this conversion with success? And to answer Ataraxis5, 4-aco-dmt is too sedating for me. It almost feels like I took several Klonapins with some 4-ho-dmt, I even find it hard to walk on 4-aco-dmt. 4-ho-dmt on the other hand provides a very nice euphoric mdma type energy with the trip. If anyone knows how to do this conversion with success please provide detailed instructions. Thanks.....
 
Because 4-ho-dmt is my favorite entheogen and the only vendor I knew of that carried it quit selling it last summer. I have 4-aco-dmt but I don't like the drowsiness that comes with the trip, it feels like I took alot of benzo's. 4-ho-dmt fells much better to me in the body and with lucidity of the mind....
 
I'm not sure whether i'm allowed to go into further detail even though this isn't much different from converting an alkaloid to freebase from a salt.
In summary though what I would suggest is using equivalent moles NaOH to moles 4-AcO-DMT (work out both their molecular weights from their chemical composition, or using ChemDraw et al.), use that in a dilute concentration (0.5M/L solutions), and apply gentle heating for an hour, and use as quicjly as possible afterward. Exclude air from the reaction vessel.
 
^^^
probs by neutralizing and then leaving out to evap, depending on the stability...i suppose it might not last long enough to evap but im not sure why that is.
 
That is clearly wrong:
4-AcO-DMT MW = 246.31 g/mol
NaOH MW = 40.00 g/mol
So for every 246.31g of 4-AcO-DMT you'd use 40 grams of NaOH.

If the amounts used are correct the pH should be near neutral (only the produced sodium ethanoate salt will contribute toward pH, so no strongly acid/base species should remain.
I would reccommend slightly acidifying the solution afterwards if you DO do this as 4-HO-DMT seems to be more stbale in acid than in base :) .
Happy trails!
 
Be careful with heating and exlcusion of air in the reaction vessel. You dont know how easy it is to build up too much pressure and there goes glass shards, poisonous fumes, caustic material, and potent drugs in ur face.

Reflux is not something I would recommend with out proper glass ware. Measuring solutions of sodium hydroxide is not something I would recommend to the untrained. The addition of NaOH to water is VERY exothermic, meaning lots of heat will be produced, and could boil over.

This is eerily close to synthesis discussion....


But yes this is a very common mechanism, used all the time, just not on this chemical. However, when you get into heating and reflux; Be careful
 
Thanks for everyones feedback! I am not a chemist, but I have done simple acid base extractions and know basic precautions. What I dont know is how long I need to heat the solution for and to what temperature it needs to be heated. What would be the best solvent for this reaction? Does it need to be refluxed or just heated? Also has anyone ever had success with the above methods mentioned, or is this all just theory?
 
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Beenhead said:
This is eerily close to synthesis discussion....
Click to expand...

Indeed. I don't think we need to stray any further, which definitely include advice of a more practical/"recipie" (God I hate that term applied to drugs, LOL) nature. Therea re other forums (one in particular) where this discussion would be more appreciated, I think.
 
euphoricnod said:
Ugh you could but it why would you want too?
Click to expand...

Because as great as 4-AcO-DMT is, 4-HO-DMT is much better! :)
 
^^
I still call it a tie. Had one of the best trips of my life on 30mg 4-aco-DMT not too long ago.

I guess further experimentation is in order ;)
 
^I would say so too.

It's too bad this conversion is only really practical for oral or rectal use (or at least it sounds like the 4-ho will degrade significantly while evaporating the water.) Still, it could be really nice for someone with just 4-AcO to be able to cut down the duration of the trip without sacrificing intensity. Well, willkell420, it looks like instead of frequent small bumps for an energetic MDMA-like buzz you'll be squirting it up your ass... frequently. Let us know how well it works, and don't forget to check that pH!
 
psood0nym said:
^I would say so too.

It's too bad this conversion is only really practical for oral or rectal use (or at least it sounds like the 4-ho will degrade significantly while evaporating the water.) Still, it could be really nice for someone with just 4-AcO to be able to cut down the duration of the trip without sacrificing intensity. Well, willkell420, it looks like instead of frequent small bumps for an energetic MDMA-like buzz you'll be squirting it up your ass... frequently. Let us know how well it works, and don't forget to check that pH!
Click to expand...

My 4-AcO-DMT trips have been very short in duration. Normal functionality in 5 hours, I would say (with some effort).
 
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