3,4-Dimethoxyphenethylamine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or O,O-dimethyldopamine, is a chemical compound of the phenethylamine family.[1] It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups.[1] It is also closely related to mescaline (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).[1]
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| Other names | Homoveratrylamine; O,O-Dimethyldopamine; DMPEA; 3,4-DMPEA; 3-Desmethoxymescaline |
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| ECHA InfoCard | 100.003.979 |
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| Formula | C10H15NO2 |
| Molar mass | 181.235 g·mol−1 |
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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 1,000 mg orally and at a dose of 10 mg intravenously.[2]
Interactions
Pharmacology
Pharmacodynamics
DMPEA shows weak affinity for serotonin receptors.[3] It induces the head-twitch response, a behavioral proxy of serotonergic psychedelic effects, in rodents.[4] DMPEA has some activity as a monoamine oxidase inhibitor.[5]
Pharmacokinetics
The elimination half-life of DMPEA is said to be less than 1 hour, indicating rapid and extensive metabolism and inactivation.[6][7]
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.[8] A similar sequence was subsequently reported by Buck and Perkin,[9] 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.[1]
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][10] 18. Nuciferine 19. Papaverine 20. Tetrabenazine 21. Tiapamil 22. Trimethoquinol 23. Veradoline 24. Verapamil.
Natural occurrence
See also
- Substituted methoxyphenethylamine
- Scaline § Related compounds
- Dimethoxyphenethylamine
- 3-Methoxytyramine
- Mescaline
- 3-Methoxy-4-ethoxyphenethylamine (MEPEA; 3-desmethoxyescaline)
- 3-Methoxy-4-allyloxyphenethylamine (MAPEA; 3-desmethoxyallylescaline)
- Pachycereus pringlei § Constituents and biological effects