Α,N-DMT


α,N-Dimethyltryptamine, also known as N-methyl-α-methyltryptamine, is a lesser-known substituted tryptamine and psychoactive drug. It is the α,N-dimethyl positional isomer of N,''N''-dimethyltryptamine.

Use and effects

α,N-DMT was synthesized and assessed by Alexander Shulgin. In his book TiHKAL, Shulgin lists the route as oral, the dosage as 50 to 100mg, and the duration as 6 to 8hours. It seemed to produce some stimulant-like effects but no apparent euphoric, entactogenic, or psychedelic effects. α,N-DMT also caused an unpleasant body load.

Pharmacology

Pharmacodynamics

Very little data exists about the pharmacological properties, metabolism, and toxicity of α,N-DMT. α,N-DMT is known to be a potent monoamine oxidase inhibitor and tryptamine or serotonin receptor antagonist. Close analogues of α,N-DMT, such as α-methyltryptamine, are known to act as monoamine releasing agents and serotonin receptor agonists.

Chemistry

α,N-DMT is the N-methylated analogue of αMT. There are notable parallels between the substituted tryptamines and substituted phenethylamines in this area in that α,N-DMT is to αMT as methamphetamine is to amphetamine.

Synthesis

The chemical synthesis of α,N-DMT has been described.

Analogues

Analogues of α,N-DMT include α-methyltryptamine, α,N,''N-TMT, α-methylserotonin, α,N'',O-TMS, α,N,''N,O''-TeMS, IPAP, and BK-NM-AMT, among others.