3,4-Dimethoxyphenethylamine

3,4-Dimethoxyphenethylamine
Clinical data
Other namesHomoveratrylamine; O,O-Dimethyldopamine; DMPEA; 3,4-DMPEA
ATC code
  • None
Identifiers
  • 2-(3,4-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.979
Chemical and physical data
FormulaC10H15NO2
Molar mass181.235 g·mol−1
3D model (JSmol)
  • O(c1ccc(cc1OC)CCN)C
  • 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 Y
  • Key:ANOUKFYBOAKOIR-UHFFFAOYSA-N Y
  (verify)

3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine or O,O-dimethyldopamine, is a chemical compound of the phenethylamine family.[1] It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups.[1] It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).[1]

Use and effects

According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, DMPEA is inactive in humans at doses of up to 1,000 mg orally and at a dose of 10 mg intravenously.[2]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

DMPEA shows weak affinity for serotonin receptors.[3] It induces the head-twitch response, a behavioral proxy of serotonergic psychedelic effects, in rodents.[4] DMPEA has some activity as a monoamine oxidase inhibitor.[5]

Pharmacokinetics

The elimination half-life of DMPEA is said to be less than 1 hour, indicating rapid and extensive metabolism and inactivation.[6][7]

Chemistry

Synthesis

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.[8] A similar sequence was subsequently reported by Buck and Perkin,[9] 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.[1]

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][10] 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.[11][12][13]

See also

References

  1. ^ a b c d Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal060.shtml
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  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. ^ Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". J Pharm Sci. 70 (8): 839–849. doi:10.1002/jps.2600700802. PMID 7031221.
  7. ^ 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.
  8. ^ A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." Ber. 42 1979-1989.
  9. ^ J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-epiBerberine." J. Chem. Soc., Trans. 125 1675-1686.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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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