3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine, also known as homoveratrylamine or O,''O''-dimethyldopamine, is a chemical compound of the phenethylamine family. 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 and to 3,4-dimethoxyamphetamine.
Use and effects
According to Alexander Shulgin in his book PiHKAL and other publications, DMPEA is inactive in humans at doses of up to 1,000mg orally and at a dose of 10mg intravenously.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 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
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
18. Nuciferine
19. Papaverine
20. Tetrabenazine
21. Tiapamil
22. Trimethoquinol
23. Veradoline
24. Verapamil.