3,4-Dimethoxyphenethylamine Explained

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.^[1] A similar sequence was subsequently reported by Buck and Perkin,^[2] 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:^{[3] [4]}

Derivatives

A known use was in the synthesis of Bevantolol.

Pharmacology

DMPEA has some activity as a monoamine oxidase inhibitor.^[5]

Occurrence

DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.^{[6] [7] [8]}

See also

• 3-Methoxytyramine
• Mescaline

External links

• DMPEA Entry in PiHKAL
• DMPEA Entry in PiHKAL • info

Notes and References

1. A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." Ber. 42 1979-1989.
2. J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-epiBerberine." J. Chem. Soc., Trans. 125 1675-1686.
3. A. Shulgin and A. Shulgin (1991). "PiHKAL A Chemical Love Story", pp. 614-616, Transform Press, Berkeley.
4. Web site: Erowid Online Books : "PIHKAL" - #60 DMPEA .
5. Keller WJ . Ferguson GG . Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase . Journal of Pharmaceutical Sciences . 66 . 7 . 1048–50 . July 1977 . 886445 . 10.1002/jps.2600660741 .
6. Lundström J . Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R . Acta Pharmaceutica Suecica . 7 . 6 . 651–66 . December 1970 . 5511715 .
7. Pummangura S . Nichols DE . McLaughlin JL . Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii . Journal of Pharmaceutical Sciences . 66 . 10 . 1485–7 . October 1977 . 925910 . 10.1002/jps.2600661037.
8. Pardanani JH . McLaughlin JL . Kondrat RW . Cooks RG . Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus . Lloydia . 40 . 6 . 585–90 . 1977 . 600028 .