Methyl-TMA

Methyl-TMA, or N-methyl-TMA, also known as N-methyl-3,4,5-trimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and 3C families.^[1][2] It is the N-methyl derivative of 3,4,5-trimethoxyamphetamine (TMA) as well as the α,N-dimethyl derivative of mescaline (3,4,5-trimethoxyphenethylamine).^[1][2]

Methyl-TMA

Clinical data
Other names	METHYL-TMA; N-Me-TMA; N-Methyl-TMA; α,N-Dimethylmescaline; N-Methyl-3,4,5-trimethoxyamphetamine
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name N-methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine
CAS Number	93675-34-4
PubChem CID	24257271
ChemSpider	23900079
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC(=C(C(=C1)OC)OC)OC)NC
InChI InChI=1S/C13H21NO3/c1-9(14-2)6-10-7-11(15-3)13(17-5)12(8-10)16-4/h7-9,14H,6H2,1-5H3 Key:XYKHBBWJSFSLRF-UHFFFAOYSA-N

Use and effects

N-Methylation of psychedelic phenethylamines has invariably greatly reduced or eliminated their hallucinogenic activity.^[3][1][4][5] Examples of this include related compounds like Beatrice (N-methyl-DOM) and methyl-DOB (N-methyl-DOB), which at assessed doses appear to be inactive as psychedelics in humans.^[6][1][4][5] According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) however, methyl-TMA showed "some mental disturbances" at the highest assessed dose of 240 mg.^[1] For comparison, the active dose range of TMA is 100 to 250 mg.^[1]

History

Methyl-TMA was first described in the scientific literature by at least 1984.^[2][7] It was subsequently described further by Shulgin in PiHKAL in 1991.^[1]

See also

• 3C (psychedelics)
• N-Methylmescaline
• Trichocereine (N,N-dimethylmescaline)
• Beatrice (N-methyl-DOM)
• N-Methyl-DOET
• N-Methyl-DOB
• N-Methyl-TMA-2
• Methyl-DMA (N-methyl-2,5-DMA)