2,4,6-Trimethoxyphenethylamine

2,4,6-Trimethoxyphenethylamine (2,4,6-TMPEA), also known as TMPEA-6, 2C-TMA-6, or ψ-2C-O, is a drug of the phenethylamine and Ψ-PEA families.^[1][2][3] It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and 2C-O (2,4,5-trimethoxyphenethylamine) as well as the α-desmethyl analogue of 2,4,6-trimethoxyamphetamine (TMA-6).^[1][2][3]

2,4,6-Trimethoxyphenethylamine

Clinical data
Other names	2,4,6-TMPEA; TMPEA-6; 2C-TMA-6; ψ-2C-O
ATC code	None
Identifiers
IUPAC name 2-(2,4,6-trimethoxyphenyl)ethanamine
CAS Number	15873-23-1
PubChem CID	21679959
ChemSpider	10296635
Chemical and physical data
Formula	C11H17NO3
Molar mass	211.261 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C(=C1)OC)CCN)OC
InChI InChI=1S/C11H17NO3/c1-13-8-6-10(14-2)9(4-5-12)11(7-8)15-3/h6-7H,4-5,12H2,1-3H3 Key:CGUNKAXAEZSOFA-UHFFFAOYSA-N

Use and effects

According to Daniel Trachsel in 2012, who cited personal communication with P. Rausch in 2009, the drug has been reported to be inactive in humans at a dose of up to 300 mg or more.^[4][3] This is similar to the case of 2C-O (inactive at >300 mg), but is in contrast to mescaline (active at ~180–360 mg) as well as TMA-6 (active at 25–50 mg).^[4][3][1]

Pharmacology

Unlike mescaline, but similarly to 2C-O, 2,4,6-TMPEA does not appear to be a substrate for amine oxidase.^[1][3][5]

History

2,4,6-TMPEA was first described in the scientific literature by 1954.^[6][5] Alexander Shulgin mentioned 2,4,6-TMPEA in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and stated that its activity in humans was unknown at the time.^[1] The compound was encountered as a novel designer drug in Russia in 2023.^[7][8]

Derivatives

A variety of derivatives of 2,4,6-TMPEA are known.^[3][4][1][2]

See also

• Substituted methoxyphenethylamine
• Trimethoxyphenethylamine
• Ψ-PEA (psychedelics)
• Mescaline (3,4,5-trimethoxyphenethylamine)
• 2C-O (2,4,5-trimethoxyphenethylamine)
• TMA-6 (2,4,6-trimethoxyamphetamine)