EMM (drug)
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| Other names | 2-Ethoxy-4,5-dimethoxyamphetamine; TMA2-2-EtO |
| Routes of administration | Oral[1] |
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| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
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| Chemical and physical data | |
| Formula | C13H21NO3 |
| Molar mass | 239.315 g·mol−1 |
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EMM, also known as 2-ethoxy-4,5-dimethoxyamphetamine or as TMA2-2-EtO, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to the psychedelic drug TMA-2.[1][2][3] It is the analogue of TMA-2 in which the methoxy group at the 2 position has been replaced with an ethoxy group.[1][2][3] In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists EMM's dose as greater than 50 mg orally and its duration as unknown.[1][2][3] The drug produced no effects at doses of up to 50 mg.[1][2] Higher doses were not tested.[1][2][3] The chemical synthesis of EMM has been described.[1][4] EMM was first described in the scientific literature by Shulgin in 1968.[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]
See also
References
- ^ a b c d e f g h i Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. EMM Entry in PiHKAL
- ^ a b c d e Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
3.3.3. 2-Ethoxy-4,5-dimethoxyphenylisopropylamine The ortho-ethoxy homolog of TMA-2 (34) is 2-ethoxy-4,5-dimethoxyphenylisopropylamine (61, EMM, 2-ethoxy-4,5-dimethoxyamphetamine). Acute trials have been conducted to levels (30 mg of the hydrochloride salt, orally) more than twice those which precipitate threshold effects with either MEM (60) or TMA-2 (34) (Shulgin, 1968). No effects either central or peripheral were noted, indicating that EMM would be less than half as potent as these latter drugs as a psychotomimetic, if indeed it had that action at all.
- ^ a b c d 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. Archived from the original on 13 July 2025.
- ^ a b Shulgin AT (January 1968). "The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine". J Med Chem. 11 (1): 186–187. doi:10.1021/jm00307a056. PMID 5637180. Archived from the original on 2025-07-12.