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4AceT (4 Acetoxy Tryptamine) Assay

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gladiolus

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I have the (dubious) honour of being the first person in the world to report an assay of 4-Ace-Tryptamine [hereafter 4acet]
I speculated that the 4-bond disactivated/rendered insusceptible monoamineoxidase , and this was why psilocin was active where DMT was not.
So I managed, after many years, to test the hypothesis with the paradigm case of 4acet; where Tryptamine, DMT, 5-OH Tryptamine (and 5-Meo DiMethylTryptamine) had all failed – in being orally active.

My original interest in the 4 series came after my first mushroom experience. At the tail end of the trip it significantly changed, and manifested a very strange feeling which stays with me still. Every time I go to the toilet I have the feeling that I’m actually urinating in a dream, and that somewhere I am wetting myself. It struck me at the time that some metabolite of psilocin was implicated in this feeling, and that this metabolite was actually a mycelial pre-cursor to psilocin. How does the mushroom synthesize psilocin from tryptophan? – is it

Tryptophan à Tryptamine à DMT à 4HO DMT

Or is it Tryptophanà 4HO Tryptophan à 4HO Tryptamine à 4HO-DMT
Or Tryptophan à Tryptamine à 4HO Tryptamine à 4HO-DMT

I knew it wasn’t the first, as the DMT experience is so different to the 4HO-DMT experience and what I was experiencing was not DMT-like. So I began to look for sources of 4HO Tryptophan and 4HO Tryptamine.

My attempts were aborted after a quote of $5K for 100g of 4HO-Tryptophan. But after waiting patiently for a few years, some 4-Ace-Tryptamine landed in my lap.
Now I’ve tried the Ace series and the Ace certainly leaves a signature; but one thing for sure is that the Ace don’t lie where the HO is inactive: thus, if 4AceT was active then it is a pretty good sign that 4HOT is active and I am one step closer to discovering my dream chemical.

DAS TRIPS
1)
0h Took 5mg of 4Acet
+45min dreariness overcomes me, very seretonergic. Go to sleep.

2)
0h Took 17mg of 4Acet
+50min sleepiness, eyelids drooping
+1h 20min very sleepy and dreamy
+2h close “Tesseract” by Alex Garland and rest my eyes. Things are getting very swimmy.
+3h I have been pummelled to and fro. My mind is all ajitter. I go to the toilet and do a very big shit, like my rectum is just opening forth and spewing. I feel like I’m very high and trippy at this stage
+4h I am lying in bed and the trip starts to muse on chinese themes. There are dragons and the Kundalini force is aching in my sciatic nerves [the Acetoxy signature]. There is a constant rush and swelling, then a subsiding of the ego. I imagine a little flame held in the belly below the navel of every one that swells and diminishes with the interior oxygen. Whoa suddenly I realize that these Chinese people I see, living in close quarters, are shielding their flame, as you would guard a lantern walking along a beach.

+5h There is a constant curliqueing of thoughts around one another, leading from the base to the head; my mind plays on it by restraining and then bellowing. I cannot control my thoughts. I am very restless in bed. My partner must be having a bad nights sleep.

+6h a solid base trippiness has been achieved. I wait an hour and then decide to end the trip by taking an antipsychotic medicament.

I have had 4Acet on the odd occasion since that last, and every time it has been very active. I remember thinking that this stuff is as visual as you can get without the visuals.

I can’t wait to try 4-Ace Tryptophan, as I am sure this will have the same seretonergic/soporific delerium but with less of a psychedelic quality. In fact, I hereby assert patent for:[“4-Acetoxy Tryptophan” for any anxiolytic, antidepressant and antipsychotic purposes.]
 
interesting...

do you think this would be good in combination with another psych?
maybe a combo with this would be the sedating psychedelic that would be mad cool
 
Hm, so 4-PO-T would probably be active then, too... bring on the good times?
 
I'm skeptical.

I've found 4-ho-nmt to be inactive at 10 mg IM and 4 mg IV, so I find it quite hard to believe that 4-ace-tryptamine could be active at similar doses. And recently I found 5-meo-nmt to be lacking all the psychedelic properties of it's dimethylated cousin.

Unless something funky is going on here, I find it hard to believe that 4-ace-tryptamine would be active. I imagine it would not be able to cross the BBB. Maybe something is special about the 4-ace, as opposed to 4-ho.

And what's up with the psilocin metabolite and the feeling of wetting yourself? That statement alone makes me question the credibility of your post.

Either way, tell us more!
 
Tryptamines and LSD often make me feel wet all over... It's a kind of weird confusion between the sensations of wetness and coldness, at times it's annoying so I don't discredit the report based on that.

The demethylated version may be able to bind to an amino acid transporter (somehow?) and could make it into the brain that way. It could also be acetylated in vivo to the substituted tryptophan and make it onto the tryptophan amino acid transporter/brain that way (arylamine n-acetyltransferase).
 
No doubt about the wetness feeling ... I've had that before. I was referring to the fact that he implicated a psilocin metabolite, since the feeling came at the end of the trip. That's a stretch ... metabolites are rarely the same as biosynthetic precursors anyway. Maybe I'm being harsh since we had that poster with multiple identities come over touting the magical 5-HO-DMT.

And I belive the biosynthetic pathway of psilocin is tryptophan --> tryptamine --> 4-HO-tryptamine, 4-HO-NMT, and 4-HO-DMT

I'm not sure where the N-methylation and phosphorylation come in after 4-HO-tryptamine is formed, but I'm pretty sure that 4-hydroxylation is the step following tryptamine formation.
 
gladiolus said:
I can’t wait to try 4-Ace Tryptophan, as I am sure this will have the same seretonergic/soporific delerium but with less of a psychedelic quality. In fact, I hereby assert patent for:[“4-Acetoxy Tryptophan” for any anxiolytic, antidepressant and antipsychotic purposes.]
Click to expand...


(4-Acetoxy-tryptamine - very interesting read.:) )

However not sure about the amino acid idea (?)
Do you have any references to back up the safety of 4-ho/4-acetoxy-Tryptophan ?

Often the amines (I.e in this case 4-acetoxy-tryptamine) are considerably different from their amino acid equivalents (I.e 4-Acetoxy-tryptophan). If your not careful amino acids analogues can mess up metabolic cycles etc (or so I understood it?).

Also (although a methyl as opposed to hydroxy) there is 4-methyl-tryptophan which is meant to be toxic to some degree (I thought?)
 
I doubt the amino acid will be good for anything. Unless it's metabolized into the amine, which I also doubt.
 
Very interesting report! You are sure of the identity of this chemical you have?

Welcome to Bluelight! I look forward to reading your posts-

peace,
S_S
 
Reminisant B said:
(4-Acetoxy-tryptamine - very interesting read.:) )

However not sure about the amino acid idea (?)
Do you have any references to back up the safety of 4-ho/4-acetoxy-Tryptophan ?

Often the amines (I.e in this case 4-acetoxy-tryptamine) are considerably different from their amino acid equivalents (I.e 4-Acetoxy-tryptophan). If your not careful amino acids analogues can mess up metabolic cycles etc (or so I understood it?).

Also (although a methyl as opposed to hydroxy) there is 4-methyl-tryptophan which is meant to be toxic to some degree (I thought?)
Click to expand...


Isnt n,n dimethyl trypthophan a known neurotoxin as well??
 
egor said:
Isnt n,n dimethyl trypthophan a known neurotoxin as well??
Click to expand...

I forgot to include that in my post. I'm pretty sure it is. I think (and we know what that's worth) it's the serotonin equivalent of 6-OHDA (6-hydroxydopamine), or MPTP (though that, as a pyridine doesn't share the close similarities these both share with the neurotransmiting system they ruin)
 
Surely 5,7-Dihydroxytryptamine is a more suitable tryptamine equivalent of 6-hydroxy-dopamine

Effects of 5,7-dihydroxytryptamine depletion of tissue serotonin levels on extracellular serotonin in the striatum assessed with in vivo microdialysis: relationship to behavior.Hall FS, Devries AC, Fong GW, Huang S, Pert A.
Laboratory of Clinical Studies, DICBR, National Institute on Alcohol Abuse and Alcoholism, Bethesda, Maryland 20892, USA. [email protected]

Effects of i.c.v. administration of 5,7-dihydroxytryptamine (5,7-DHT) on biochemistry and behavior were studied in awake Sprague-Dawley rats. It was found that 5,7-DHT depletion of striatal tissue levels of serotonin (5-HT) does not diminish extracellular levels until substantial depletions occur. This finding is similar to those observed after 6-hydroxydopamine lesions of the brain dopamine systems. Although varying amounts of 5,7-DHT produced serotonin depletions in striatal tissue, decreases in extracellular levels were only observed at tissue depletions greater than 60% compared to saline-injected control subjects. Thus, the effects of serotonin lesions which produce only moderate depletions may not be the result of decreased extracellular serotonin, but instead may be the result of compensatory changes in remaining neurons which maintain normal extracellular serotonin concentrations. Different degrees of striatal serotonin depletion were associated with opposite behavioral effects. Moderate levels of serotonin depletion (50-75%) produced evidence of increased anxiety, while these effects were no longer seen in rats with more severe 5-HT depletions
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Can easily believe the amino acid n,n-dimethyltryptophan is neurotoxic. The idea of altering and testing unknown amino acids always sounds worrying.
 
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I was recently struck out of the blue with the idea that DMT could be snuck into the body if it looked more like Tryptophan, and that the addition of a carboxyl group in the alpha position might confer an alpha-methyl-like protection against MAOI. I've checked some indexes, and it appears that this N,N-dimethyl compound is unknown or unmentioned. I was wondering if this is a feasible idea, and whether the synthesis would be overly difficult?

-- Jim


Dear Jim:
Three quick answers: No, no, and no. But your idea opens up a little known area of amino acid chemistry and plant products that is not widely appreciated. Let me take your questions one at a time.

(...missing info, complete version from webpage link below)

N-Methyltryptophan (L-(+)-Abrine, or simply Abrine) is widely distributed throughout the plant world. It is a major component of the Rosary Pea (the Jequirity Bean) which has the botanical name Abrus precatorius and which has enjoyed some popular use as an insecticide. The toxicity of this rather poisonous plant is apparently not in its alkaloid composition but in its protein fraction. Abrine itself has shown some tumor inhibition properties in rats, but the search for possible pharmacology was disappointing. But be careful. The name "Abrin" is quite a different item. It is an extremely toxic protein from this same plant. The seeds of this plant have been used for poisoning people, and are very nasty.

N,N-Dimethyltryptophan has also been found in the Jequirity Bean seeds and several other plants, but other than having being described as a plant growth inhibitor, it is unknown pharmacologically.

N,N,N-Trimethyltryptophan has been isolated from many plants but has not been explored pharmacologically. Its most common name is Lenticine, but in some of the more obscure botanical literature you will find the names Hypaphorine and Glyyunnanenine.

Your third question dealt with their synthesis. All of them are easily made from S-tryptophan by discrete N-methylation, and all are easily separated from one-another by chromatography. But, if you intend to explore their psychopharmacological potential, remember that their structure pretty much denies entry into the brain. They may indeed be active, but that action is not likely to be psychedelic in nature. Be cautious.

-- Dr. Shulgin
Click to expand...

http://www.cognitiveliberty.org/shulgin/adsarchive/dmt.htm
 
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I doubt the stability of the compound,the acetyl group will wander to the amine of the tryptamine.
 
reply to concerns

Hi everyone, thanks for your comments.

In regards to my little anecdote about me feeling I'm wetting myself, well, strange things happen on shroom trips, this being quite a peculiar bodily sensation. With regards to the whole speculation on the dream-like effects being produced by a metabolite that was also a precursor: OK it's not science, it's not meant to be science, i was just relating how it seemed to me intuitively at the time, those many many years ago, there is no rational justification, and I must admit, even retrospectively such a hypothesis does seem unlikely. I related that story just to introduce historically how I had come to have interest in this compound no matter how crazy my poorly formed speculations might have been. As an exercise in writing, designed to be captivating. Please hesitate to make this relevant to my credibility as a whole.

Of all the posts so far, i am very very interested in Dondante relating that IM and IV of 4HO NMT had no effect. This really stumps me. How could it be? My source for this chemical is pretty well impeccable. There is a real issue here that needs to be cleaned up. Maybe 4Ace NMT would be inactive too? Or maybe 4HO-Tryptamine would be inactive? Or maybe Dondante you might try say 25mg orally of the 4HO NMT just to confirm, for example?

Oh, I realize that I am on far shakier ground with the 4HO-Tryptophan. I too do not like the idea of messing with amino's. Intuitively I feel that the methylated-tryptophans are a bad way to go. But we must distinguish between modifications to the tail and modifications made on the 4 and 5 positions of the hex ring. But this post is not about whether you have had the peculiar dream-wetting sensations, or about the fungoloid route of 4 addition, or really about 4Ace tryptophan, except as divergent issues. The main thing is that i am relating an experience report about 4AceT; I urge that I am genuine. Maybe someone else one day will confirm the bioactivity and add to the experience reports.
 
Well, it's certainly possible it's active (The 4-AcO-T). AMT demonstrated that tryptamines need not have alkyl groups on the nitrogen to be psychedelic. This warrants further investigation.
 
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