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acetylation of 5-HO-DMT to 5-AcO-DMT (bufotenine)

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69ron

69ron

Esteemed member
Apparently 5-AcO-DMT is able to cross the blood brain barrier better than 5-HO-DMT(bufotenine), so it produces far less side effects.

I know that acetic anhydride is used to acetylate 5-HO-DMT into 5-AcO-DMT. The same thing works for psilocin.

It’s next to impossible to get acetic anhydride.

I’ve read that glacial acetic acid, or even just vinegar, can also be used for acetylation, but the reaction is slow, taking about 8 hours.

Will this work with 5-HO-DMT? If you mix it for 8 hours in strong acetic acid, would 5-AcO-DMT form?

Does acetic acid actually work for this reaction or is that just rumor?
 
Just so you guys take this seriously:
1. How is Accoya® wood made?
The technology behind Accoya® wood is based on wood acetylation, a process that has been studied by scientists for more than 75 years and proven to be an outstanding method of improving the technical properties of wood. The process essentially alters the actual cell structure of wood by transforming free hydroxyl groups into acetyl groups. Acetyl groups simply consist of hydrogen, oxygen and carbon and are already present in all wood species (ranging from 1% to 8% by weight) and can be derived independently from acetic acid, i.e. vinegar. Thus, the process does not introduce anything to the wood that does not naturally occur in it.
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So apparently vinegar is strong enough for industrial use in wood acetylation. SWIM is going to try using vinegar and see what happens.
 
Wow, full of great ideas 69ron!

But what you propose is sound, as long as one finds a way for the esterification between acetic acid 5-HO-DMT. Typically one would need some catalyst like concentrated sulphuric acid.

But in the case of the latter, would 5-HO-DMT survive this very low pH? Would someone be safer refluxing the whole reaction?

Yet I am not a qualified chemist. Some chemist could possibly be able to make better suggestions; how about looking at the esterification of salicylic acid to form acetylsalycilic acid? This may be a standard procedure to perform and directly analogous to the 5-HO-DMT ---> 5-AcO-DMT reaction.
 
I've looked at the acetylation of salicylic acid. I've seen different methods. Some use a catalyst and some don't. I see a lot of mixed information out there. The wood industry normally uses acetic acid anhydride, and some catalyst, but I've seen some that just use vinegar and nothing else.

I’ve read that the original acetylation of salicylic acid used vinegar until it was discovered that acetic acid anhydride worked much better and much faster. At least that's what I've read. I don't know if its true or even practical to use vinegar.

SWIM is testing the idea out right now. So far the bufotenine (amber, impure bufotenine) is changing color from amber to slightly red. It’s been mixing for 3 hours now at room temperature. Something is definitely happening to it.

It this works, then great, if not, SWIM needs to get make some acidic anhydride. He cannot buy it!

Is there a way to easily make acidic anhydride?
 
Take a look at this paper:


It says that
Aspirin (acetylsalicylic acid) is formed by the reaction between acetic acid and salicylic acid.

This esterification reaction is reversible, however, and the presence of water can lead to hydrolysis of the aspirin.
Thus, an anhydrous (“without water”) reagent could lead to better yields of product. This reagent is acetic anhydride.
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Imagine, mixing Yopo with vinegar for 24 hours, then extracting it. After reading up on this, I’m positive you’d get some 5-AcO-DMT out of the 5-HO-DMT. According to the info on aspirin, the yield won’t be great, but it should work.

Basically, the reason for using acetic anhydride is to increase the yields. But there may be another way to prevent the hydrolysis. Any ideas?
 
Like Infundibulum said, i'm used to using a little sulfuric acid to catalyze the esterification of an acid and an alcohol. I don't think you need a great deal of it in the reaction for it to make the reaction proceed much quicker. I think it'd certainly be worth trying, with or without sulfuric acid.
 
what would the dosage be for 5-AcO-DMT? it must be a little less than 5-HO-DMT i would guess.. has this chemical been tested?
 
lorax said:
what would the dosage be for 5-AcO-DMT? it must be a little less than 5-HO-DMT i would guess.. has this chemical been tested?
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If the 4- substituted tryptamines are any indication, you will need a higher dosage than with 5-ho-dmt, but the effects will be more pleasant.
 
5-AcO-DMT weighs 20 % more than 5-HO-DMT, so a 20% larger dose should be needed. It should convert to 5-HO-DMT in the brain, just like 4-AcO-DMT converts to 4-HO-DMT (psilocin) in the brain. And it should have much less side effects because it should enter the brain more easily than 5-HO-DMT does. 5-HO-DMT causes side effects; instead of it all going into the brain, because it's very water soluble, a lot stays in the body and causes bodily effects. But 5-AcO-DMT wouldn’t have that problem because it’s much less water soluble.

I don't know what the exact dosage is. I’ve read its active at 15 mg smoked.

Here's a tech I found for this conversion
Dissolve 4.1g bufotenin in 20 ml 1M NaOH and evaporate to dryness under N2. Dry in vacuum at 90C and dissolve in 50 ml dimethoxyethane. Add to 1.9 g acetyl-Cl in 50 ml in 50 ml dimethoxyethane and stir four hours at room temperature. Add to dilute NaHCO3 and CHCl3; shake and dry, evaporate in vacuum the CHCl3 layer to get 5-Acetoxy-dimethyltryptamine. This should be active at maybe 15 mg smoked, possibly orally as well. I can't remember off hand.
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I believe that tech dissolves the bufotenine in 20 ml 1M sodium hydroxide which would bring the pH to 14. That’s enough to destroy the bufotenine. So I guess it’s knocking off the hydrogen from the 5-HO-DMT, leaving a damaged and highly reactive 5-O-DMT. They dry it under nitrogen to prevent the 5-O-DMT from oxidizing. Then they dissolve it in dimethoxyethane, acetone would probably work instead. They use that instead of water because water would hydrolyze it back to 5-HO-DMT. Then they add acetyl chloride, which is next to impossible to get. They stir for 4 hours to complete the reaction (no catalyst is used). Then they freebase it with dilute sodium bicarbonate and extract it with chloroform.

The problem is dimethoxyethane is hard to get and acetyl chloride is extremely hard to get. So that tech is useless to SWIM.

It also seems overly complex compared to aspirin synthesis which works with just vinegar (to a certain degree).

I’m wondering about this tech:

Dissolve bufotenine in glacial acetic acid and magnesium sulfate anhydride. The magnesium sulfate anhydride is a drying agent and should absorb all the excess water preventing hydrolysis? Mix for 4 hours. Then freebase it with dilute sodium bicarbonate and extract it with DCM.

Are there any obvious holes in that tech? Glacial acetic acid, magnesium sulfate, sodium bicarbonate, and DCM are all easy to get.
 
69ron said:
Dissolve bufotenine in glacial acetic acid and magnesium sulfate anhydride. The magnesium sulfate anhydride is a drying agent and should absorb all the excess water preventing hydrolysis? Mix for 4 hours. Then freebase it with dilute sodium bicarbonate and extract it with DCM.

Are there any obvious holes in that tech? Glacial acetic acid, magnesium sulfate, sodium bicarbonate, and DCM are all easy to get.
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It really sounds fine to me. Magnesium sulfate may be the thirsty catalyst actually helping the esterification. The successful product of the esterification will produce one molecule of water; if in the anhydrous environment of the glacial acetic acid the water is trapped by the magnesium sulphate, this will drive the reaction towards 5-AcO-dmt synthesis, eventually completely esterifying all the 5-HO-dmt.

Definitely worth a try, maybe also using different catalysts for the said purpose? Some drops of 100% H2SO4 or even dry silika beads in the glacial acetic acid would serve the exact same purpose; as sink for water molecules.
 
I would assume not.

The ester 4-HOPO3-dmt (or psilocybin) is dephosphorylated to 4-HO-dmt (psilocin) inside the body most likely due to the acidic pH of the stomach or less likely due to the action of a phosphatase enzyme.

Similarly, 4-AcO-dmt might be hydrolysed to 4-HO-dmt again due to the action of the high pH of the stomach or less likely due to the action of some deacetylase enzyme.
 
SWIM's vinegar experiment is complete. He continuously mixed 20 ml vinegar and 100 mg of impure amber bufotenine on a hotplate set to 120 C for 4 hours. The 50 ml flask only got hot but never boiled.

During the experiment the liquid changed color from amber to very dark burgundy.

After 4 hours he let it cool down and added 2.5 grams of sodium carbonate and extracted into 20 ml DCM 5 times. He distilled the DCM down to 20 ml and then evaporated it.

He was left with 63 mg of a solid light amber mass which easily scraped up and was dry and crystalline.

Unlike the amber bufotenine, it’s now lighter in color, is now odorless and nearly tasteless.

He unfortunately has built up tolerance to the visual effect of bufotenine so he needs to wait a few days before he can test it out to see if any 5-AcO-DMT formed from it. He’s excited because the color, smell, and taste are now different. It could just be that it’s more pure now, but SWIM doesn’t think that’s the reason. Even pure bufotenine tastes bitter. This stuff is now practically tasteless.

In a few days SWIM will try smoking 10 mg of it and see what happens.
 
Well, it seems like the simple vinegar process worked, but not completely. The effects were different, cleaner, but not by much. I don't think the conversion was complete.

One problem is that SWIM doesn’t have pure bufotenine to work with. He’s been trying for months to purify bufotenine just for this type of work and he’s been unsuccessful at it.

Most of the side effects SWIM’s bufotenine has are from the amber (actually brown when separated) substance in it. His current batch of bufotenine is mostly the amber contaminant which causes very unpleasant nausea when you smoke it. It was extracted form poor quality Vilca seeds.

He’s going to try purifying his amber bufotenine via vacuum liquid chromatography as soon as some supplies arrive. Once he purifies his bufotenine he will try this conversion again using a better process that should yield better results.
 
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