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| Other names | Homoveratrylamine;O,O-Dimethyldopamine; DMPEA; 3,4-DMPEA |
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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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3,4-Dimethoxyphenethylamine (DMPEA or3,4-DMPEA), also known ashomoveratrylamine orO,O-dimethyldopamine, is achemical compound of thephenethylamine family.[1] It is ananalogue of the major humanneurotransmitterdopamine where the 3- and 4-positionhydroxygroups have been replaced withmethoxy groups.[1] It is also closely related tomescaline which is 3,4,5-trimethoxyphenethylamine and to3,4-dimethoxyamphetamine (3,4-DMA).[1]
According toAlexander Shulgin in his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications, DMPEA is inactive in humans at doses of up to 1,000 mgorally and at a dose of 10 mgintravenously.[2]
DMPEA shows weakaffinity forserotonin receptors.[3] It induces thehead-twitch response, a behavioral proxy ofserotonergic psychedelic effects, in rodents.[4] DMPEA has some activity as amonoamine oxidase inhibitor.[5]
Theelimination half-life of DMPEA is said to be less than 1 hour, indicating rapid and extensivemetabolism and inactivation.[6][7]
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 fromvanillin.[8] A similar sequence was subsequently reported by Buck and Perkin,[9] as follows:
A much shorter synthesis is given by Shulgin and Shulgin.[1]
Identified uses for DMPEA includes the following list of agents:
1.Bevantolol.2.Bisobrin3.Bometolol4.Buquiterine5.Denopamine6.Dobutamine7.Dopamine8.Dopexamine9.Dramedilol10.Drotaverine11.Ecastolol12.Falipamil13.Gallopamil14.Methopholine15.Mixidine16.Mefeclorazine17.Nigellimine [4594-02-9][10]18.Nuciferine19.Papaverine20.Tetrabenazine21.Tiapamil22.Trimethoquinol23.Veradoline24.Verapamil.
DMPEA occursnaturally along withmescaline in various species ofcacti such asSan Pedro andPeruvian Torch.[11][12][13]
