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

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.
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