2,α-Dimethyltryptamine

2,α-Dimethyltryptamine (2,α-DMT), also known as 2-methyl-α-methyltryptamine (2-Me-αMT or 2-Me-AMT), is a tryptamine and a lesser-known psychedelic drug.^[1] It is the 2,α-dimethyl analogue of DMT and the 2-methyl derivative of α-methyltryptamine (αMT or AMT).^[1]

2,α-Dimethyltryptamine

Clinical data
Other names	2,α-DMT; 2-Methyl-α-methyltryptamine; 2-Methyl-AMT; 2-Methyl-αMT; 2-Me-AMT; 2-Me-αMT
Routes of administration	Oral
ATC code	None
Identifiers
IUPAC name 1-(2-methyl-1H-indol-3-yl)propan-2-amine
CAS Number	4966-28-3 Y
ChemSpider	23511903 Y
UNII	QAH3JR2679
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image
SMILES Cc1c(c2ccccc2[nH]1)CC(C)N
InChI InChI=1S/C12H16N2/c1-8(13)7-11-9(2)14-12-6-4-3-5-10(11)12/h3-6,8,14H,7,13H2,1-2H3 Y Key:AXZQFXRPULJFQK-UHFFFAOYSA-N Y
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Use and effects

Alexander Shulgin lists the dose as 300 to 500 mg, and the duration as 7 to 10 hours in his book TiHKAL (Tryptamines I Have Known and Loved).^[1] 2,α-DMT causes mydriasis and paresthesia.^[1] It also produces a calm, drunk-like feeling.^[1]

Chemistry

Synthesis

The chemical synthesis of 2,α-DMT has been described.^[1]

Analogues

Analogues of 2,α-DMT (2-methyl-AMT) include 2-methyltryptamine (2-MT or 2-Me-T), 2,N,N-TMT (2-methyl-DMT), 2-methyl-DET, and 5-MeO-2-TMT (2-methyl-5-MeO-DMT), among others.^[1]

History

The chemical synthesis of 2,α-DMT was first reported in 1965.^[2]

See also

• Substituted tryptamine