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ARCHIVE:  November 18, 2002

5-Me-DMT or 5,N,N-TMT
(5,N,N-trimethyltryptamine)

Dear Dr. Shulgin:

I have been unable to find any information regarding the compound that has a methyl group at the 5-position of DMT. I am not confusing it with 5-MeO-DMT. Do you know anything about this chemical?

-- A Concerned Explorer

Dear Explorer:

This is a very good question about a compound that is virtually unknown. N,N-Dimethyltryptamine (DMT) has a hydrogen atom at the indole 5-position, and it is a very well known and broadly studied material. Two additional 5-substituted dimethyltryptamines are also well known; these are bufotenine with an HO- group (a hydroxy group) and 5-MeO-DMT with a MeO- group (a methoxy group) at this position. The compound that you are asking about has a Me- group there (a methyl group) and it has been abbreviated as either 5-Me-DMT or 5,N,N-TMT (5,N,N-trimethyltryptamine).

5-Me-DMT was first synthesized by E. H. Young, and one of the few papers that discusses its pharmacology was an animal research project published by R. A. Glennon and P. K. Gessner. Their studies involved the induced contractions of strips of stomach fundus of rats, which is known to rank tryptamines in an order parallel to their ability to block LSD binding in brain homogenates. Some 27 tryptamines were studied by them, including the 5-H and the 5-MeO- analogues of this 5-methyl compound. The degree of contraction has been used as a measure of brain receptor affinity, and in this assay these three compounds were shown to rank in increasing potency in the order DMT < 5-Me-DMT < 5-MeO-DMT.

An intriguing parallel to this study involves N-methyl-N-isopropyl homologues. A study by D. J. McKenna, D. B. Repke and S. J. Peroutka has described the affinity of some two dozen tryptamines to the 5HT-2 serotonin receptor that is usually associated with hallucinogenic activity. Here they studied the three above-mentioned compounds in brain homogenates, but with this alternate nitrogen substitution pattern. Here, again, the order of increased potency was found to be MIPT < 5-Me-MIPT < 5-MeO-MIPT. The references for these three papers are: Young, J. Chem. Soc. 3493 (1958), Glennon et al, J. Med. Chem. 22:428-432 (1979) and McKenna et al., Neuropharmacology 29:193-198 (1989).

But to answer your question, there must be human experimentation to establish human activity and, to my knowledge, 5-Me-DMT has never been tried in man.

-- Dr. Shulgin

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