3,4- Di

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

phenethylamine (DMPEA) is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy

group A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic ide ...

s have been replaced with

groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine.

Chemistry

One of the earliest syntheses of DMPEA (then referred to as "homoveratrylamine") was that of Pictet and Finkelstein, who made it in a multi-step sequence starting from

vanillin Vanillin is an organic compound with the molecular formula . It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used ...

. A similar sequence was subsequently reported by Buck and Perkin, as follows: : 3,4-Dimethoxybenzaldehyde (veratraldehyde) → 3,4-Dimethoxycinnamic acid → 3,4-Dimethoxyphenylpropionic acid → 3,4-Dimethoxyphenylpropionamide → 3,4-Dimethoxyphenethylamine A much shorter synthesis is given by Shulgin and Shulgin:A. Shulgin and A. Shulgin (1991). "PiHKAL A Chemical Love Story", pp. 614-616, Transform Press, Berkeley.

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 A cactus (, or less commonly, cactus) is a member of the plant family Cactaceae, a family comprising about 127 genera with some 1750 known species of the order Caryophyllales. The word ''cactus'' derives, through Latin, from the Ancient Greek ...

such as San Pedro and Peruvian Torch.

References

External links