Chemistry:Α,N-DMT

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Short description: Chemical compound


α,N-DMT
Clinical data
Other namesα,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]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
  (verify)

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]

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.

See also

  • Substituted α-alkyltryptamine

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press, 425. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  2. ↑ "N-Methyl-alpha-methyl-tryptamine: a potent monoamine oxidase inhibitor and tryptamine antagonist". Biochemical Pharmacology 11 (6): 481–485. June 1962. doi:10.1016/0006-2952(62)90231-9. PMID 13920062. 
  3. ↑ "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters 24 (19): 4754–4758. October 2014. doi:10.1016/j.bmcl.2014.07.062. PMID 25193229. 



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