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 images Image
PubChem 8421
Properties
C10H15NO2
Molar mass 181.23 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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[edit]

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[edit]

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

See also[edit]

References[edit]

  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. ^ a b "Erowid Online Books : "PIHKAL" - #60 DMPEA". 
  5. ^ Keller WJ, Ferguson GG (July 1977). "Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase". Journal of Pharmaceutical Sciences 66 (7): 1048–50. doi:10.1002/jps.2600660741. PMID 886445. 
  6. ^ Lundström J (December 1970). "Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R". Acta Pharmaceutica Suecica 7 (6): 651–66. PMID 5511715. 
  7. ^ Pummangura S, Nichols DE, McLaughlin JL (October 1977). "Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii". Journal of Pharmaceutical Sciences 66 (10): 1485–7. doi:10.1002/jps.2600661037. PMID 925910. 
  8. ^ Pardanani JH, McLaughlin JL, Kondrat RW, Cooks RG (1977). "Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus". Lloydia 40 (6): 585–90. PMID 600028. 

External links[edit]