3,4-Dimethoxyphenethylamine

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3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine v2.svg
3,4-Dimethoxyphenethylamine 3D ball.png
Names
Preferred IUPAC name
2-(3,4-Dimethoxyphenyl)ethan-1-amine
Other names
O,O-Dimethyldopamine; Homoveratrylamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.979 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: ANOUKFYBOAKOIR-UHFFFAOYSA-N Yes check.svgY
  • 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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3,4-Dimethoxyphenethylamine (DMPEA), also known as O,O-dimethyldopamine, 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 and to 3,4-dimethoxyamphetamine (3,4-DMA).

Contents

Pharmacology

DMPEA shows weak affinity for serotonin receptors. [1] It induces the head-twitch response, a behavioral proxy of serotonergic psychedelic effects, in rodents. [2] However, according to Alexander Shulgin, it was inactive in humans at doses of 1,000 mg orally and 10 mg intravenously. [3]

DMPEA has some activity as a monoamine oxidase inhibitor. [4]

The elimination half-life of DMPEA is said to be less than 1 hour, indicating rapid and extensive metabolism and inactivation. [5] [6]

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. [7] A similar sequence was subsequently reported by Buck and Perkin, [8] 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: [9] [10]

Derivatives

Identified uses for DMPEA includes the following list of agents:

1. Bevantolol. 2. Bisobrin 3. Bometolol 4. Buquiterine 5. Denopamine 6. Dobutamine 7. Dopamine 8. Dopexamine 9. Dramedilol 10. Drotaverine 11. Ecastolol 12. Falipamil 13. Gallopamil 14. Methopholine 15. Mixidine 16. Mefeclorazine 17. Nigellimine [4594-02-9] [11] 18. Nuciferine 19. Papaverine 20. Tetrabenazine 21. Tiapamil 22. Trimethoquinol 23. Veradoline 24. Verapamil.

Natural occurrence

DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch. [12] [13] [14]

See also

References

  1. ↑ Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID   7365744.
  2. ↑ Corne SJ, Pickering RW, Warner BT (February 1963). "A method for assessing the effects of drugs on the central actions of 5-hydroxytryptamine". Br J Pharmacol Chemother. 20 (1): 106–120. doi:10.1111/j.1476-5381.1963.tb01302.x. PMC   1703746 . PMID   14023050.
  3. ↑ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4 . Retrieved 1 February 2025.
  4. ↑ 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.
  5. ↑ Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". J Pharm Sci. 70 (8): 839–849. doi:10.1002/jps.2600700802. PMID   7031221.
  6. ↑ Schweitzer JW, Friedhoff AJ (March 1968). "The metabolism of dimethoxyphenethylamine, a compound found in the urine of schizophrenics". Am J Psychiatry. 124 (9): 1249–1253. doi:10.1176/ajp.124.9.1249. PMID   5637912.
  7. ↑ A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." Ber.42 1979-1989.
  8. ↑ J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-epiBerberine." J. Chem. Soc., Trans.125 1675-1686.
  9. ↑ A. Shulgin and A. Shulgin (1991). "PiHKAL A Chemical Love Story", pp. 614-616, Transform Press, Berkeley. ISBN   0-9630096-0-5
  10. ↑ "Erowid Online Books : "PIHKAL" - #60 DMPEA".
  11. ↑ Atta-ur-Rahman, Malik, S., Zaman, K. (May 1992). "Nigellimine: A New Isoquinoline Alkaloid from the Seeds of Nigella sativa" . Journal of Natural Products. 55 (5): 676–678. doi:10.1021/np50083a020 . Retrieved 27 October 2025.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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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