3,4-Dimethoxyphenethylamine

3,4-Dimethoxyphenethylamine

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3,4-Dimethoxyphenethylamine

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Identifiers
CAS number 120-20-7 YesY
PubChem 8421
ChemSpider 8114 YesY
ChEBI CHEBI:136995 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H15NO2
Molar mass 181.23 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Chemistry

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:

3,4-Dimethoxybenzaldehyde (veratraldehyde) → 3,4-Dimethoxycinnamic acid3,4-Dimethoxyphenylpropionic acid3,4-Dimethoxyphenylpropionamide → 3,4-Dimethoxyphenethylamine

A much shorter synthesis is given by Shulgin and Shulgin:[3][4]

3,4-Dimethoxybenzaldehyde is reacted with nitromethane in the presence of ammonium acetate/acetic acid to give the corresponding β-nitrostyrene, which is then reduced with LiAlH4 to give 3,4-dimethoxyphenethylamine.

Pharmacology/Clinical

In the book PiHKAL, Shulgin describes DMPEA as producing no central effects in humans when tested even with very high doses, such as 1,000 mg orally or 10 mg via intravenous injection.[4] However, DMPEA has been shown to have some activity as a monoamine oxidase inhibitor.[5]

Occurrence

DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.[6][7][8]

See also

References

External links

  • DMPEA Entry in PiHKAL • info