Trimethoxyamphetamine Trimethoxyamphetamine TMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine cactus alkaloid mescaline. The TMAs are substituted amphetamines, however, their action does not resemble that of the unsubstituted compound "amphetamine", which is a stimulant and not a psychedelic. It is reported that some TMA's elicit a range of emotions ranging from sadness to empathy and euphoria. TMA was first synthesized by Hey, in 1947. Synthesis data
Mescaline at the two meta positions with respect to the alkyl substituent, experiences a final methylation at the 4 carbon by a guaiacol-O-methyltransferase, which also operates by a SAM-dependent mechanism. This final methylation step results in the production of mescaline. Phenylalanine serves as a precursor by first being converted to -tyrosine by L-amino acid hydroxylase. Once converted, it follows the same pathway as described above. Mescaline was first synthesized in 1919 by Ernst Späth from 3,4,5-trimethoxybenzoyl chloride. Subsequent to this, numerous approaches utilizing different starting materials have been developed. Notable examples include the following: Tolerance builds with repeated usage, lasting for