3,4-Dimethoxyphenethylamine

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3,4-Dimethoxyphenethylamine
Skeletal formula of 3,4-dimethoxyphenethylamine
Ball-and-stick model of the 3,4-dimethoxyphenethylamine molecule
Names
IUPAC name
2-(3,4-dimethoxyphenyl)ethylamine
Identifiers
120-20-7 YesY
ChEBI CHEBI:136995 YesY
ChEMBL ChEMBL26019 YesY
ChemSpider 8114 YesY
Jmol 3D model Interactive image
PubChem 8421
  • InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3 YesY
    Key: ANOUKFYBOAKOIR-UHFFFAOYSA-N YesY
  • InChI=1/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
    Key: ANOUKFYBOAKOIR-UHFFFAOYAB
  • O(c1ccc(cc1OC)CCN)C
Properties
C10H15NO2
Molar mass 181.23 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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 acid → 3,4-Dimethoxyphenylpropionic acid → 3,4-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]

Uses

DMPEA is used as a precursor in the syntheses of a number of pharmaceutical drugs including bisobrin, papaverine, methopholine, verapamil, gallopamil, tiapamil, tetrabenazine, and trimethoquinol.

See also

References

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External links

  1. ↑ A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." Ber. 42 1979-1989.
  2. ↑ J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-epiBerberine." J. Chem. Soc., Trans. 125 1675-1686.
  3. ↑ A. Shulgin and A. Shulgin (1991). "PiHKAL A Chemical Love Story", pp. 614-616, Transform Press, Berkeley. ISBN 0-9630096-0-5
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
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