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2,4-Dimethoxyphenethylamine

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2,4-Dimethoxyphenethylamine
Clinical data
Other names2,4-DMPEA; DMPEA-3; 24; 24DMP
Drug classSerotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(2,4-dimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15NO2
Molar mass181.235 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1)CCN)OC
  • InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)10(7-9)13-2/h3-4,7H,5-6,11H2,1-2H3
  • Key:YDTQAPOROITHCN-UHFFFAOYSA-N

2,4-Dimethoxyphenethylamine (2,4-DMPEA), also known as DMPEA-3, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).[1][2][3] It is one of the positional isomers of dimethoxyphenethylamine.[1]

The in-vitro metabolism of 2,3-DMPEA and its effects on cat behavior have been studied.[1][2][3] The drug is known to act as a low-potency partial agonist of the serotonin 5-HT2A receptor (Ki = 202–999 nM; EC50Tooltip half-maximal effective concentration = 832–4,034 nM; EmaxTooltip maximal efficacy = 67–83%).[4][5] The effects of 2,4-DMPEA in humans have not been reported and are unknown.[1]

2,4-DMPEA was first described in the scientific literature by at least 1964.[1][2] It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[1]

NBOMe and NBOH derivatives with potent serotonin 5-HT2A receptor agonism, such as 24-NBOMe and 24-NBOH, have been synthesized and studied.[4][5]

See also

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References

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  1. ^ a b c d e f Shulgin A, Manning T, Daley PF (2011). "#47. 2,4-DMPEA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 82–83. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. ^ a b c Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines". Ala J Med Sci. 1: 417–429. PMID 14230671.
  3. ^ a b Clark LC, Benington F, Morin RD (May 1965). "The effects of ring-methoxyl groups on biological deamination of phenethylamines". J Med Chem. 8 (3): 353–355. doi:10.1021/jm00327a016. PMID 14323146.
  4. ^ a b Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Mol Pharmacol. 70 (6): 1956–1964. doi:10.1124/mol.106.028720. PMID 17000863.
  5. ^ a b Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
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