Α,N-DMT
Chemical compound
From Wikipedia, the free encyclopedia
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.[1] It is the α,N-dimethyl positional isomer of N,N-dimethyltryptamine (N,N-DMT).[1]
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| Other names | α,N-Dimethyltryptamine; α,N-DMT; N-Methyl-α-methyltryptamine; N-Methyl-αMT; N-Methyl-AMT; NM-AMT; NM-αMT; Methamtryptamine; SK&F-7024; SKF-7024; Ro 3-1715; RO-3-1715 |
| Routes of administration | Oral[1] |
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| Formula | C12H16N2 |
| Molar mass | 188.274 g·mol−1 |
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Use and effects
α,N-DMT was synthesized and assessed by Alexander Shulgin.[1] In his book TiHKAL (Tryptamines I Have Known and Loved), Shulgin lists the route as oral, the dosage as 50 to 100 mg, and the duration as 6 to 8 hours.[1] It seemed to produce some stimulant-like effects but no apparent euphoric, entactogenic, or psychedelic effects.[1] α,N-DMT also caused an unpleasant body load.[1]
Pharmacology
Pharmacodynamics
Very little data exists about the pharmacological properties, metabolism, and toxicity of α,N-DMT.[1] α,N-DMT is known to be a potent monoamine oxidase inhibitor and tryptamine or serotonin receptor antagonist.[2][1] Close analogues of α,N-DMT, such as α-methyltryptamine (αMT), are known to act as monoamine releasing agents and serotonin receptor agonists.[3]
Chemistry
α,N-DMT is the N-methylated analogue of αMT.[1] 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).[1]
Synthesis
The chemical synthesis of α,N-DMT has been described.[1]
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.