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Chemical compound From Wikipedia, the free encyclopedia
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.
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Names | |
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Preferred IUPAC name
2-(3,4-Dimethoxyphenyl)ethan-1-amine | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.979 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C10H15NO2 | |
Molar mass | 181.23 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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:
A much shorter synthesis is given by Shulgin and Shulgin:[3][4]
A known use was in the synthesis of Bevantolol.
DMPEA has some activity as a monoamine oxidase inhibitor.[5]
DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.[6][7][8]
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