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ARCHIVE: September 19, 2002
DMT & Tryptophan
Dear Dr. Shulgin:
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?
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.
In principle, the effectiveness of the body's amine group remover, the monoamineoxidase enzyme, is blocked by a lumpy group (such as a methyl group) located right next to it. But this is not a methyl group; it is a monster negatively charged carboxy group which effectively destroys the innocent amine character of that tryptamine nitrogen atom. The compound you mention would be a full fledged amino acid and, as such, would be blocked from entry into the brain by its hydrophilic salt nature.
And what is this N-methyl tryptophan DMT analogue you are mentioning? Actually I have inferred three compounds from your question, N-methyltryptophan, N,N-dimethyltryptophan and N,N,N-trimethyltryptophan. Each of these is known, each is an alkaloid found in the world of plants, and none of these has been explored in man as a possible psychedelic drug.
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
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.
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