3,4-Dimethylphenethylamine
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| Clinical data | |
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| Other names | DMePEA; 3,4-DMePEA |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.199.619 |
| Chemical and physical data | |
| Formula | C10H15N |
| Molar mass | 149.237 g·mol−1 |
| 3D model (JSmol) | |
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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]
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
[edit]- Substituted phenethylamine
- Dimethylphenethylamine
- Xylopropamine (3,4-dimethylamphetamine; 3,4-DMeA)
- 3,4-Dimethylmethcathinone
- 3,4-Dimethoxyphenethylamine (DMPEA)
- 3,4-Dimethoxyamphetamine (3,4-DMA)
References
[edit]- ^ a b c d e f 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.
- ^ a b c d 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.
- ^ a b c 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.
- ^ a b 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.
- ^ 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.