4-ACO-DMT Acid Hydrolysis

[maranello551]

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.

So can one boil the acetic acid with the 4-aco-dmt in it? Where is the dissolved oxygen? In the 4-aco-dmt or in the vinegar?

So could one add say a gram of 4-aco-dmt to a small vial of hot 5% acetic acid white vinegar and wait and eventually have a vial of 4-ho-dmt tincture? What else would have to be done?

 

[downwardsfromzero]

Hit it repeatedly with a large hammer, with the words 'acid hydrolysis' attached on a Post-It (tm) note...

 

[pitubo]

So can one boil the acetic acid with the 4-aco-dmt in it? Where is the dissolved oxygen? In the 4-aco-dmt or in the vinegar?

First boil the vinegar (this expels the dissolved oxygen), then add the 4-AcO-DMT and continue heating.

So could one add say a gram of 4-aco-dmt to a small vial of hot 5% acetic acid white vinegar and wait and eventually have a vial of 4-ho-dmt tincture? What else would have to be done?

In principle, yes. Practically speaking, I am not sure about the details, like how long to heat for complete conversion, or how much to heat (reflux or, say, 80 degrees celsius?).

In the end, you may want to neutralize the catalytic acid and the hydrolyzed acid with some baking soda.

One things is certain: you will not have a tincture at the end. A tincture is an alcoholic solution.

 

[Nathanial.Dread]

Look at some of the literature posted in that link about protection/deprotection. There are many protocols posted there that could be adapted for food safe, kitchen chemistry.

Blessings
~ND

 

[maranello551]

First boil the vinegar (this expels the dissolved oxygen), then add the 4-AcO-DMT and continue heating.

Can one boil the vinegar with a microwave?

 

[pitubo]

Can one boil the vinegar with a microwave?

Certainly one can. But would this be useful to purge dissolved gases from it? Probably not.

In order to expel most of the dissolved gases, the vinegar would need some sustained low boiling for (I guess) five or ten minutes. With most regular microwave ovens, the energy control just isn't fine grained enough to allow for sustained controlled low boiling. Most microwave ovens have no "low heat" setting, only variably timed intervals of maximum power.

Sometimes a microwave oven doesn't even boil a liquid properly, but instead causes it to overheat, only to suddenly explode (literally) into boiling. This explosive boiling, when it happens, also tends to happen just as you reach inside to pick up the vessel. This is not fun, obviously.

Additionally, an attempt at extended boiling of the small amount of vinegar needed for your hypothetical 1 gram 4-AcO-DMT hydrolysis in a microwave oven might overheat and damage the magnetron. The microwave energy must go somewhere if it cannot be absorbed by the vinegar.

 

[maranello551]

Can one boil the vinegar with a microwave?

Certainly one can. But would this be useful to purge dissolved gases from it? Probably not.

In order to expel most of the dissolved gases, the vinegar would need some sustained low boiling for (I guess) five or ten minutes. With most regular microwave ovens, the energy control just isn't fine grained enough to allow for sustained controlled low boiling. Most microwave ovens have no "low heat" setting, only variably timed intervals of maximum power.

Sometimes a microwave oven doesn't even boil a liquid properly, but instead causes it to overheat, only to suddenly explode (literally) into boiling. This explosive boiling, when it happens, also tends to happen just as you reach inside to pick up the vessel. This is not fun, obviously.

Additionally, an attempt at extended boiling of the small amount of vinegar needed for your hypothetical 1 gram 4-AcO-DMT hydrolysis in a microwave oven might overheat and damage the magnetron. The microwave energy must go somewhere if it cannot be absorbed by the vinegar.

Fair enough. May I ask what issue removing gas trapped in the vinegar solves? If one doesn't take this step, what could happen.

Say one hypothetically successfully completed the conversion....he'd be supposedly left with a large amount of 4-ho-dmt in a vinegar solution ( I was under the impression that a tincture could be vinegar based, but I may be wrong. ) I fear this may be unstable....? Or would would psilocin be more stable in vinegar than in air? Can one do an A/B on a dilute acetic acid solution to retrieve isolated 4-ho-dmt?

 

[Nathanial.Dread]

Can I ask what the point of all this is? It would be kind of pain to get the psilocin out of solution (and I'm not sure how stable it would be), and this is a process your body naturally does anyway.

Acetic acid will boil off at 119 deg. C, psilocin at 176 deg C, so you could use distillation to clean up your product: once all the acetic acid had been boiled off (can you TLC for AA?), you should have a reasonably good product. Keep the boil low, and top off your solution with dH2O periodically.

Blessings
~ND

 

[maranello551]

Can I ask what the point of all this is? It would be kind of pain to get the psilocin out of solution (and I'm not sure how stable it would be), and this is a process your body naturally does anyway.

...because I do not believe 4-aco-dmt converts to psilocin in vivo.....because they feel completely different at anything other than baseline.....4-aco-dmt makes swim feel sick.....4-ho-dmt makes swim feel like God has arrived.

 

[downwardsfromzero]

May I ask what issue removing gas trapped in the vinegar solves? If one doesn't take this step, what could happen.

Specifically to drive away dissolved oxygen. Psilocin is highly sensitive to oxidation, as previously mentioned.
If this is not done, more of your psilocin will be destroyed in the putative hydrolysis attempt.


Also note that even small quantities of dissolved iron greatly accelerate oxidation of psilocin.

...because I do not believe 4-aco-dmdt converts to psilocin in vivo.....because they feel cokmpletely different at anything other than baseline.....4-aco-dmt makes swim feel sick.....4-ho-dmt makes swim feel like God has arrived.

Are you sure you could tell them apart in a double-blind trial? What is your sample size (i.e. how many times have you done each one)? And have you for sure really had pure psilocin? Or definitely 4-AcODMT for that matter?

After a bit of thinking about this conundrum, it seems that a hydride-based reduction might feasibly cleave off the acetate group, and it wouldn't even need boron tribromide for cleaving off a resulting ethoxy group because the acetate wouldn't reduce that far. Viz, you could try a borohydride (commercially available for legitimate purposes and fairly safe-ish - watch out for the hydrogen, don't blow yourself up). This ticks several boxes - OTC; simple; acidic environment; low risk of oxidation; non-toxic workup. It should be no more dangerous than a Zn/HCl reduction, assuming the person attempting the process is competent in practical chemistry. Hmmm... :?

Using the appropriate esterase enzyme might be another approach.

Acetic acid will boil off at 119 deg. C, psilocin at 176 deg C, so you could use distillation to clean up your product: once all the acetic acid had been boiled off (can you TLC for AA?), you should have a reasonably good product. Keep the boil low, and top off your solution with dH2O periodically.

I doubt much psilocin would survive that boiling process unless you were fortunate enough to have a rotary evaporator and a good vacuum pump! Maybe bubbling nitrogen through a warm solution would carry the solvent off without so much loss of product.

Titration or a pH paper would be better than TLC for testing for acetic acid. It will take ages to boil off all the acid while constantly dripping in dH2O as an entrainer, I'd definitely recommend using some kind of inert atmosphere and proper glassware for this if at all possible.

Another thing to do might be to add an appropriate amount of citric acid to the boil so that the citrate remains instead of the acetate.

 

[pitubo]

...because I do not believe 4-aco-dmdt converts to psilocin in vivo.....because they feel cokmpletely different at anything other than baseline.....4-aco-dmt makes swim feel sick.....4-ho-dmt makes swim feel like God has arrived.

Are you sure you could tell them apart in a double-blind trial? What is your sample size (i.e. how many times have you done each one)? And have you for sure really had pure psilocin? Or definitely 4-AcODMT for that matter?

More or less my thoughts as well. Another factor is the influence that the form of the ingested substance has. I have had very different effects from whole mushrooms and from ethanolic extracts.

[..] hydride-based reduction [..] boron tribromide [..] Viz, you could try a borohydride (commercially available [..] don't blow yourself up) [..] assuming the person attempting the process is competent in practical chemistry. Hmmm... :?

:!:

Using the appropriate esterase enzyme might be another approach.

That might be the most reasonable method accesible for people like "swim": toss the 4-AcO-DMT in some (preboiled) hot vinegar together with some pulverized or blenderized shrooms. The shrooms will contribute the enzymes and some bonus 4-HO-DMT. Stir for 15 minutes. Consume before the 4-HO-DMT has oxidized.

 

[Nathanial.Dread]

You'd probably need fresh shrooms - I'd worry about the enzymes denaturing if they'd been dried or stored for a long while.

I love this idea though, it's such a great thought!

Blessings
~ND

 

[downwardsfromzero]

That might be the most reasonable method accesible for people like "swim": toss the 4-AcO-DMT in some (preboiled) hot vinegar together with some pulverized or blenderized shrooms. The shrooms will contribute the enzymes and some bonus 4-HO-DMT. Stir for 15 minutes. Consume before the 4-HO-DMT has oxidized.

But are mushroom phosphatases sufficiently general to cleave acetates also? Plus it would be better to use a buffer solution rather than vinegar to avoid denaturing the enzymes, also keep temperature below ~40°C for the same reason.

 

[pitubo]

I cannot find it right now, but IIRC an article by Jochen Gartz describes a protocol where dried mushrooms are kept for 15 minutes in 80 degrees celcius dilute acetic. He then bases to pH 8 or thereabouts and immediately extracts with chloroform. The article is a more recent one than the 1994 one that can be found everywhere on the net.

 

[maranello551]

because I do not believe 4-aco-dmdt converts to psilocin in vivo.....because they feel cokmpletely different at anything other than baseline.....4-aco-dmt makes swim feel sick.....4-ho-dmt makes swim feel like God has arrived.

Are you sure you could tell them apart in a double-blind trial? What is your sample size (i.e. how many times have you done each one)? And have you for sure really had pure psilocin? Or definitely 4-AcODMT for that matter?

Never tried pure psilocin.

Just around 100 mushroom experiences

Five 4-aco-dmt experiences

I know it was 4-aco-dmt

Never tried pure psilocin, but the 4-aco-dmt felt distinctly artificial. It felt more like LSD or even an NBOME than it did like mushrooms.....and it caused me fever-like symptoms, physical discomfort, jittery hands.......it's not the same stuff. It's just not. 4-aco-dmt feels like something a junkie made to try to mimic LSD, and the more I take, the worse I feel physically - the opposite of the way mushrooms are for me.

No, how I take themk changes very little. Sure, eating mushrooms vs lemon tek vs tea all is a little different, but all basically feels like dmt to an extent.....4-aco feel like something way different.....again, more like an NBOME

 

[Nathanial.Dread]

The problem with that kind of anecdotal evidence is that it's not blinded. You know whether you're taking a 'natural' or 'artificial' compound, and given how much mindset and preconceptions can affect a trip, it doesn't seem at all impossible to me that this alone may cause the perceived differences in quality.

I personally think that this placebo (or nocebo) effect underlies a lot of the differences people report between different drugs. I imagine that, under properly double-blinded conditions, most psychedelics would be much harder to tell apart than we generally report.

Blessings
~ND

 

[maranello551]

The problem with that kind of anecdotal evidence is that it's not blinded. You know whether you're taking a 'natural' or 'artificial' compound, and given how much mindset and preconceptions can affect a trip, it doesn't seem at all impossible to me that this alone may cause the perceived differences in quality.

I personally think that this placebo (or nocebo) effect underlies a lot of the differences people report between different drugs. I imagine that, under properly double-blinded conditions, most psychedelics would be much harder to tell apart than we generally report.

Blessings
~ND

What? Are you being serious? I've done mushrooms a literal hundred times. I know what it's like. It doesn't have to be blinded. I know a pear tastes different from an apple even though it's not a blind test lol. It wasn't a placebo difference. It was a major difference. One hurt and one didn't. One made me physically sick and one made me feel like God. i regularly dose from 5-10g dry cubensis. I've dosed 10-35mg 4-aco-dmt. The test needs not be blind. The differences pecome more pronounced the higher the dosage of each......the more you dose of each, the more different they are from each other. They are only reminiscently similar at threshold doses, anything above, and 4-aco-dmt is as different from mushrooms as LSD is.

Do you need a blind test to tell if something is weed or mushrooms? I doubt it. This is the same to me. They feel like 2 different drugs, and the higher you dose, the more true this will ring.

 

[pitubo]

How do you know what the purity of your 4-AcO-DMT is? Are you sure that it is actual 4-AcO-DMT that is making you sick and not an impurity or something else altogether?

The form of ingestion can influence the absorption profile and this in turn can have a strong effect on the subjective quality of the experience. One time I took a lot of ethanolic mushroom tincture and it make me feel so sick that I wondered if there had been harmalas in the tincture and that I was experiencing serotonin syndrome. But after checking, it was reconfirmed that there hadn't any harmalas in the tincture, only extracted plain mushrooms. In hindsight, I speculate that the symptoms that I felt may have been caused by an unusually large sudden influx of 4-HO-DMT overwhelming my receptors and enzymes. I have has similarly high doses of dried mushrooms (over 15 gram) and the effects were different. I also became a little sick, but that was purely from the bulk of mushroom proteins consumed on an empty stomach.

 

[wolf8312]

After a bit of thinking about this conundrum, it seems that a hydride-based reduction might feasibly cleave off the acetate group, and it wouldn't even need boron tribromide for cleaving off a resulting ethoxy group because the acetate wouldn't reduce that far. Viz, you could try a borohydride (commercially available for legitimate purposes and fairly safe-ish - watch out for the hydrogen, don't blow yourself up).

Sorry I dont understand. Can you maybe show me or explain the proposed mechanism for such a reduction? When you say 'hydride based reduction' you are talking LAH or other hydrogen nucleophiles right?

As far as I can work out a hydrogen nucleophile would attack the electrophilic carbonyl, and push its electrons up onto the oxygen which would then need to be neutralized.

 

[Nathanial.Dread]

The problem with that kind of anecdotal evidence is that it's not blinded. You know whether you're taking a 'natural' or 'artificial' compound, and given how much mindset and preconceptions can affect a trip, it doesn't seem at all impossible to me that this alone may cause the perceived differences in quality.

I personally think that this placebo (or nocebo) effect underlies a lot of the differences people report between different drugs. I imagine that, under properly double-blinded conditions, most psychedelics would be much harder to tell apart than we generally report.

Blessings
~ND

What? Are you being serious? I've done mushrooms a literal hundred times. I know what it's like. It doesn't have to be blinded. I know a pear tastes different from an apple even though it's not a blind test lol. It wasn't a placebo difference. It was a major difference. One hurt and one didn't. One made me physically sick and one made me feel like God. i regularly dose from 5-10g dry cubensis. I've dosed 10-35mg 4-aco-dmt. The test needs not be blind. The differences pecome more pronounced the higher the dosage of each......the more you dose of each, the more different they are from each other. They are only reminiscently similar at threshold doses, anything above, and 4-aco-dmt is as different from mushrooms as LSD is.

Do you need a blind test to tell if something is weed or mushrooms? I doubt it. This is the same to me. They feel like 2 different drugs, and the higher you dose, the more true this will ring.

Do the experiment, see what results you come up with. Dissolve several analogous doses of 4-AcO and psilocybin in water, blind yourself and a friend to conditions, and see how reliably you can figure out which one is which. You'd need multiple trials (or people) to help out with the experiment if you wanted enough statistical power to make even the most rudimentary conclusions, but it could quite easily be done.

Blessings
~ND