3,4-Dimethoxyphenethylamine


3,4-Dimethoxyphenethylamine is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine.

Chemistry

One of the earliest syntheses of DMPEA was that of Pictet and Finkelstein, who made it in a multi-step sequence starting from vanillin. A similar sequence was subsequently reported by Buck and Perkin, as follows:
A much shorter synthesis is given by Shulgin and Shulgin:

Derivatives

A known use was in the synthesis of Bevantolol.

Pharmacology

DMPEA has some activity as a monoamine oxidase inhibitor.

Occurrence

DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.