3,4-Dimethoxyphenethylamine

Use and effects

According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, DMPEA is inactive in humans at doses of up to 1,000mg orally and at a dose of 10mg intravenously.

Interactions

Pharmacology

Pharmacodynamics

DMPEA shows weak affinity for serotonin receptors. It induces the head-twitch response, a behavioral proxy of serotonergic psychedelic effects, in rodents. DMPEA has some activity as a monoamine oxidase inhibitor.

Pharmacokinetics

The elimination half-life of DMPEA is said to be less than 1hour, indicating rapid and extensive metabolism and inactivation.

Chemistry

Synthesis

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

Identified uses for DMPEA includes the following list of agents:

1. Bevantolol.
2. Bisobrin
3. Bometolol
4. Buquiterine
5. Denopamine
6. Dobutamine
7. Dopamine
8. Dopexamine
9. Dramedilol
10. Drotaverine
11. Ecastolol
12. Falipamil
13. Gallopamil
14. Methopholine
15. Mixidine
16. Mefeclorazine
17. Nigellimine [4594-02-9]
18. Nuciferine
19. Papaverine
20. Tetrabenazine
21. Tiapamil
22. Trimethoquinol
23. Veradoline
24. Verapamil.

Natural occurrence

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

References

References

1. (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
2. (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem.
3. (February 1963). "A method for assessing the effects of drugs on the central actions of 5-hydroxytryptamine". Br J Pharmacol Chemother.
4. Keller WJ. (July 1977). "Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase". Journal of Pharmaceutical Sciences.
5. (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". J Pharm Sci.
6. (March 1968). "The metabolism of dimethoxyphenethylamine, a compound found in the urine of schizophrenics". Am J Psychiatry.
7. A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." ''Ber.'' '''42''' 1979-1989.
8. J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-epiBerberine." ''J. Chem. Soc., Trans.'' '''125''' 1675-1686.
9. {{CitePiHKAL http://www.erowid.org/library/books_online/pihkal/pihkal060.shtml
10. (May 1992). "Nigellimine: A New Isoquinoline Alkaloid from the Seeds of Nigella sativa". Journal of Natural Products.
11. Lundström J. (December 1970). "Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R". Acta Pharmaceutica Suecica.
12. Pummangura S. (October 1977). "Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii". Journal of Pharmaceutical Sciences.
13. Pardanani JH. (1977). "Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus". Lloydia.