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α,N-DMT

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Chemical compound
Pharmaceutical 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
  • 1-(1H-indol-3-yl)-N-methylpropan-2-amine
CAS Number
PubChemCID
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 namesSK&F-7024,Ro 3-1715), also known asN-methyl-α-methyltryptamine (N-methyl-αMT), is a lesser-knownsubstituted tryptamine andpsychoactive drug.[1] It is the α,N-dimethylpositional isomer ofN,N-dimethyltryptamine (N,N-DMT).[1]

α,N-DMT wassynthesized and assessed byAlexander Shulgin.[1] In his bookTiHKAL (Tryptamines I Have Known and Loved), Shulgin lists theroute asoral, the dosage as 50 to 100 mg, and theduration as 6 to 8 hours.[1] It seemed to produce somestimulant-like effects but no apparenteuphoric,entactogenic, orpsychedelic effects.[1] α,N-DMT also caused an unpleasantbody load.[1]

Very little data exists about thepharmacological properties,metabolism, andtoxicity of α,N-DMT.[1] α,N-DMT is known to be apotentmonoamine oxidase inhibitor andtryptamine orserotonin receptor antagonist.[2][1] Close analogues of α,N-DMT, such asα-methyltryptamine (αMT), are known to act asmonoamine releasing agents andserotonin receptor agonists.[3]

α,N-DMT is theN-methylated analogue of αMT.[1] There are notable parallels between the substituted tryptamines andsubstituted phenethylamines here in that α,N-DMT is to αMT asmethamphetamine (N-methyl-α-methylphenethylamine) is toamphetamine (α-methylphenethylamine).[1]

See also

[edit]

References

[edit]
  1. ^abcdefghijkShulgin 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.

External links

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Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
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HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
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