3,4-Dimethylphenethylamine

Last updated

3,4-Dimethylphenethylamine
3,4-Dimethylphenethylamine.svg
Clinical data
Other namesDMePEA; 3,4-DMePEA
Identifiers
  • 2-(3,4-dimethylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard 100.199.619 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H15N
Molar mass 149.237 g·mol−1
3D model (JSmol)
  • CC1=C(C=C(C=C1)CCN)C
  • InChI=1S/C10H15N/c1-8-3-4-10(5-6-11)7-9(8)2/h3-4,7H,5-6,11H2,1-2H3
  • Key:IQXUVSNUSQIQCJ-UHFFFAOYSA-N

3,4-Dimethylphenethylamine (DMePEA) is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA). [1] [2] [3] [4] It is one of the positional isomers of dimethylphenethylamine. [1] [2]

Contents

It produces a strong rage reaction (which has been thought may be a correlate of hallucinogenic activity) and other behavioral effects in cats [3] [5] and produces body tremors and salivation in rats. [1] [2] [4] The effects of DMePEA in humans have not been reported and are unknown. [1]

DMePEA was first described in the scientific literature by 1960. [1] [2] [3] It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . [1]

See also

References

  1. 1 2 3 4 5 6 Shulgin A, Manning T, Daley PF (2011). "#43. DMePEA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 77–78. ISBN   978-0-9630096-3-0. OCLC   709667010.
  2. 1 2 3 4 Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97. Mescaline is by no means the most potent hallucinogenic phenylethylamine (Table 3.2). Early studies (Benington, Morin, and Clark, 1960) showed that 3,4,5-trimethyl-, 4-methyl-, 4-chloro-, 3,5-dimethyl-t-methoxy-, 3,4-dichloro-, 3,4-dimethyl-, and 3,5-dimethoxy-4-methyl-phenylethylamine, all produced the sham rage response in cats, a syndrome that has been equated with hallucinogenic activity in man.
  3. 1 2 3 Benington F, Morin R, Clark Jr L (1960). "Notes- Mescaline Analogs. X. 3,4-Dimethyl-, 3,4-Dichloro- and 3,5-Dimethoxy-4-methyl-β-phenethylamines". The Journal of Organic Chemistry. 25 (11): 2066–2067. doi:10.1021/jo01081a626. ISSN   0022-3263 . Retrieved 2 July 2025.
  4. 1 2 Schweitzer JW, Friedhoff AJ, Roll FJ (August 1969). "A new tremorgen: 3,4-dimethylphenethylamine". Archives Internationales de Pharmacodynamie et de Therapie. 180 (2): 385–390. PMID   5348408.
  5. ↑ Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines". The Alabama Journal of Medical Sciences. 1: 417–429. PMID   14230671.
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