2,5-Dimethoxy-4-ethoxyamphetamine
Template:Short description Template:Drugbox
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
In his book PiHKAL, Alexander Shulgin lists the active dose range of MEM as 20 to 50Script error: No such module "String".mg orally and the duration as 10 to 14Script error: No such module "String".hours.[1][3] According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.[1]
Pharmacology
| 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
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
A variety of derivatives of MEM have been developed and studied, for instance by Daniel Trachsel and colleagues.[11][12] These include MPM, MIPM, MALM, MMALM, MFEM, MDFEM, and MTFEM, among others.[11][12]
History
MEM was first synthesized by Alexander Shulgin.[1][2] It was first described by him in the scientific literature by 1968.[2]
See also
References
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External links
- MEM - Isomer Design
- The Small & Handy MEM Thread - Bluelight
- MEM - PiHKAL - Erowid
- MEM - PiHKAL - Isomer Design
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