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.^[1] It is the α,N-dimethyl positional isomer of N,N-dimethyltryptamine (N,N-DMT).^[1]

α,N-DMT

Clinical data
Other names	α,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
IUPAC name 1-(1H-indol-3-yl)-N-methylpropan-2-amine
CAS Number	299-24-1 Y
PubChem CID	3724428
ChemSpider	2955156 Y
UNII	L8WKV7YXX3
ChEBI	CHEBI:59024
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1cccc2c1c(c[nH]2)CC(NC)C
InChI 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 Y Key:HUWIYJREHSBOEO-UHFFFAOYSA-N Y
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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

• Indolylpropylaminopentane (α,N-DPT)

References

1. 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.

External links

• α,N-DMT Entry in TIHKAL
• α,N-DMT Entry in TiHKAL • info