2,5-Dimethoxy-4-ethoxyamphetamine
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| Other names | 2,5-Dimethoxy-4-ethoxyamphetamine; 4-Ethoxy-2,5-dimethoxyamphetamine; MEM |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor agonist; Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Pharmacokinetic data | |
| Elimination half-life | 10–14 hours[1] |
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| Chemical and physical data | |
| Formula | C13H21NO3 |
| Molar mass | 239.315 g·mol−1 |
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2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.[1] It was first described by Alexander Shulgin by 1968.[2]
Dosage and effects
[edit]In his book PiHKAL, Alexander Shulgin lists the active dose range of MEM as 20 to 50 mg orally and the duration as 10 to 14 hours.[1][3] According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.[1]
Pharmacology
[edit]| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | >10,000 |
| 5-HT1B | >10,000 |
| 5-HT1D | >10,000 |
| 5-HT1E | >10,000 |
| 5-HT1F | ND |
| 5-HT2A | 73.0–3,948 (Ki) 47.5–295 (EC50) 88–105% (Emax) |
| 5-HT2B | 64.5–763 (Ki) 437–557 (EC50) 70–96% (Emax) |
| 5-HT2C | 124–>10,000 (Ki) 29.9–248 (EC50) 98–129% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT4 | ND |
| 5-HT5A | >10,000 |
| 5-HT6 | >10,000 |
| 5-HT7 | 7,156 |
| α1A, α1B | >10,000 |
| α1D | ND |
| α2A–α2C | >10,000 |
| β1, β2 | >10,000 |
| β3 | ND |
| D1–D5 | >10,000 |
| H1–H4 | >10,000 |
| M1–M5 | >10,000 |
| I1 | >10,000 |
| σ1 | 5,077 |
| σ2 | >10,000 |
| TAAR1 | ND |
| SERT | >10,000 (Ki) |
| NET | >10,000 (Ki) |
| DAT | >10,000 (Ki) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [4][5][6][7][8][9][10] | |
MEM is a serotonergic psychedelic and acts as a selective serotonin 5-HT2 receptor agonist.[6][7][8][9][10] It is specifically a full agonist of the serotonin 5-HT2A and 5-HT2C receptors and to a lesser extent is a partial to full agonist of the serotonin 5-HT2B receptor.[6][7][9] The psychedelic effects of MEM are thought to be mediated by serotonin 5-HT2A receptor activation.[7]
Chemistry
[edit]MEM, also known as 2,5-dimethoxy-4-ethoxyamphetamine, is a phenethylamine, amphetamine, and DOx derivative. It is the analogue and derivative of 2,4,5-trimethoxyamphetamine (TMA) in which a 4-ethoxy group is present instead of a 4-methoxy group.
Derivatives
[edit]A variety of derivatives of MEM have been developed and studied, for instance by Daniel Trachsel and colleagues.[11][12] These include MMALM, MALM, MFEM, MDFEM, MTFEM, and MIPM, among others.[11][12]
History
[edit]MEM was first synthesized by Alexander Shulgin.[1][2] It was first described by him in the scientific literature by 1968.[2]
See also
[edit]References
[edit]- ^ a b c d e f Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
- ^ a b c 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.
- ^ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167: 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152.
Table 4 Human potency data for selected hallucinogens. [...]
- ^ "Kᵢ Database". PDSP. 28 March 2025. Retrieved 28 March 2025.
- ^ Liu, Tiqing. "BindingDB BDBM50005255 (+/-)2-(4-Ethoxy-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::2-(4-Ethoxy-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL8225". BindingDB. Retrieved 28 March 2025.
- ^ a b c Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
- ^ a b c d Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1): 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
- ^ a b Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch Pharmacol. 359 (1): 1–6. doi:10.1007/pl00005315. PMID 9933142.
- ^ a b c Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M (2023). "Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors". Front Pharmacol. 14: 1101290. doi:10.3389/fphar.2023.1101290. PMC 9902381. PMID 36762110.
- ^ a b Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, Smith C, Egan C, Davis K, Mattson MV (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug Alcohol Depend. 60 (2): 121–132. doi:10.1016/s0376-8716(99)00148-9. PMID 10940539.
- ^ a b Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines" (PDF). Front Pharmacol. 10: 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671.
- ^ a b Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.