α,N-DMT

α,N-Dimethyltryptamine (α,N-DMT; developmental code names SK&F-7024, Ro 3-1715), also known as N-methyl-α-methyltryptamine (N-methyl-αMT), is a lesser-known substituted tryptamine and psychoactive drug. It is the α,N-dimethyl positional isomer of N,N-dimethyltryptamine (N,N-DMT).

Use and effects

α,N-DMT was synthesized and assessed by Alexander Shulgin. In his book TiHKAL (Tryptamines I Have Known and Loved), 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 (αMT), 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 (N-methyl-α-methylphenethylamine) is to amphetamine (α-methylphenethylamine).

Synthesis

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

Analogues

Analogues of α,N-DMT include α-methyltryptamine (AMT), α,N,N-TMT (N,N-dimethyl-AMT), α-methylserotonin (AMS; 5-HO-AMT), α,N,O-TMS (5-methoxy-N-methyl-AMT), α,N,N,O-TeMS (5-methoxy-N,N-dimethyl-AMT), IPAP (α,N-DPT), and BK-NM-AMT (β-keto-N-methyl-AMT), among others.