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

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

Research.


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.

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.

What if you use a base first and then an acid as two seperate steps?

I worked through the basic reaction and it left me with an oxidized 4-0-DMT molecule because it was always deprotonated by the more unstable OH molecules. With its ring and reasonance it was better able to hold the charge than any free OH.

But I wonder if this is what you mean when you say the ring is very fragile and prone to destruction in basic conditions?

Do you mean prone to deprotonation by the base (OH) or are there other perhaps more troublesome reactions that I havent yet considered?

The redox process hydroquinone - quinone can be seen as a sequence of proton and electron transfers. In the first step, deprotonation leads to a phenoxide ion which is transformed into a phenoxy radical by a one-electron oxidation. Dissociation of the second OH group generates the radical anion semiquinone followed by a second one-electron oxidation to give benzoquinone. All intermediates are resonance stabilized. Similar redox processes are frequently observed in nature.

Nobody is shooting at you, right?

The point of that being?

The redox process hydroquinone - quinone can be seen as a sequence of proton and electron transfers. In the first step, deprotonation leads to a phenoxide ion which is transformed into a phenoxy radical by a one-electron oxidation.

Anyway this has been interesting and I've learned a few things, or at least learned that I need to learn quite a few things.

You really might as well just lemmon tek shrooms I think.

Sorry, but that won't lead to the result desired.......a lemon tek feels a lot less like 4-aco-dmt than eating mushrooms straight up does.....so clearly something doesn't make sense here..

Hi, you never bothered to respond to my question to you. Did you ever compare pure 4-HO-DMT against pure 4-AcO-DMT? (and was the latter that you claim to have had pure at all?)

In 2005, a unifying mechanism for the psychic action and toxicity of abused drugs was proposed based on electron transfer (ET)[1]. Among the principal ET functionalities, one of the main ones is the quinone category which is usually formed as a metabolite. The abused drugs that appear to function by the quinone route include amphetamine, methamphetamine, ecstasy, morphine, heroin, phenobarbital, and aspirin. Recently, mescaline has been added to the list [2].
Psilocybin, present in certain mushrooms, is a hallucinogen belonging to the tryptamine family. It has been banned in most countries. In vivo, psilocybin is converted by dephosphorylation into the phenol psilocin which also exhibits psychedelic (hallucinogenic) properties. Studies have been carried out entailing enzymatic oxidation which provide important evidence concerning the mechanistic mode. The product from psilocin, possessing a deep blue color, is believed to contain an o-quinone structure [3]. A similar result was obtained in a subsequent investigation in which the product was assigned either an o-quinone or iminoquinone structure [4].
Psilocybin yielded a similar result in accord with facile cleavage to psilocin. o-Quinones display quite favorable ET properties. The data fit nicely into the prior unifying framework involving participation of ET entities in the physiological activity [1]. There has been scant attention paid to action mode at the fundamental molecular level.
Pharmacological studies were reported on receptor participation [5]. Psilocin behaves as a partial agonist at the 5-HT2A serotonin receptor in the brain. It is not surprising that the effects are somewhat related to those of serotonin which possesses a closely related structure.
In conclusion, the quinoidal metabolite from enzymatic oxidation of psilocin and its capability to undergo ET which apparently plays a crucial role in drug action, support the earlier mechanistic hypothesis.