• Source: 3,4-Dimethoxyphenethylamine

3,4-Dimethoxyphenethylamine (DMPEA) 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 (then referred to as "homoveratrylamine") 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:

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:




= 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.




See also


3-Methoxytyramine
Mescaline




References






External links


DMPEA Entry in PiHKAL
DMPEA Entry in PiHKAL • info

Kata Kunci Pencarian:

• 3,4-Dimethoxyphenethylamine
• Dimethoxyphenethylamine
• Alexander Shulgin
• Trichocereus macrogonus var. pachanoi
• Dimethoxyamphetamine
• N,N-Dimethyldopamine
• DME (psychedelic)
• List of Schedule I controlled substances (U.S.)
• 3-Methoxytyramine
• C10H15NO2