3,4-Dimethoxyphenethylamine

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
Other names
O,O-Dimethyldopamine; Homoveratrylamine
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).
checkY verify (what is checkY☒N ?)
Infobox references

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).

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

A known use was in the synthesis of bevantolol.

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. ^ 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. ^ 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.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.