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α,N-DMT

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α,N-DMT
Clinical data
Other namesα,N-Dimethyltryptamine; α,N-DMT; N-Methyl-α-methyltryptamine; N-Methyl-αMT; N-Methyl-AMT; Methamtryptamine; SK&F-7024; SKF-7024; Ro 3-1715; RO-3-1715
Routes of
administration		Oral[1]
Identifiers
  • 1-(1H-indol-3-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
  • c1cccc2c1c(c[nH]2)CC(NC)C
  • InChI=1S/C12H16N2/c1-9(13-2)7-10-8-14-12-6-4-3-5-11(10)12/h3-6,8-9,13-14H,7H2,1-2H3 checkY
  • Key:HUWIYJREHSBOEO-UHFFFAOYSA-N checkY
  (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]

α,N-DMT was first synthesized 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]

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]

α,N-DMT is the N-methylated analogue of αMT.[1] There are notable parallels between the substituted tryptamines and substituted phenethylamines here in that α,N-DMT is to αMT as methamphetamine (N-methyl-α-methylphenethylamine) is to amphetamine (α-methylphenethylamine).[1]

See also

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References

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  1. ^ a b c d e f g h i j k Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 425. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ^ Tedeschi DH, Tedeschi RE, Fowler PJ, Green H, Fellows EJ (June 1962). "N-Methyl-alpha-methyl-tryptamine: a potent monoamine oxidase inhibitor and tryptamine antagonist". Biochemical Pharmacology. 11 (6): 481–485. doi:10.1016/0006-2952(62)90231-9. PMID 13920062.
  3. ^ Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
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