3,4-Dimethoxyphenethylamine

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.

3,4-Dimethoxyphenethylamine
Skeletal formula of 3,4-dimethoxyphenethylamine
Ball-and-stick model of the 3,4-dimethoxyphenethylamine molecule
Names
Preferred IUPAC name
2-(3,4-Dimethoxyphenyl)ethan-1-amine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.979
UNII
  • 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 checkY
    Key: ANOUKFYBOAKOIR-UHFFFAOYSA-N checkY
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

Derivatives

A known use was in the synthesis of Bevantolol.

Pharmacology

DMPEA has 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
  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. "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.
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