MME (psychedelic)
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| Names | |
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| Preferred IUPAC name
1-(5-Ethoxy-2,4-dimethoxyphenyl)propan-2-amine | |
| Other names
2,4-Dimethoxy-5-ethoxyamphetamine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C13H21NO3 | |
| Molar mass | 239.315 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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MME, or 2,4-dimethoxy-5-ethoxyamphetamine, is a lesser-known psychedelic drug. It is a dimethoxy-ethoxy analog of TMA-2. MME was first synthesized by Alexander Shulgin from ethylvanillin. In his book PiHKAL, the minimum dosage is listed as 40 mg and above, and the duration listed as 6–10 hours.[1] Shulgin gives MME a ++ on the Shulgin Rating Scale.[2]
Pharmacology and toxicology
[edit]Shulgin describes in his book an experiment with MME, in which he admistered varying amounts of the drug to mice via injections.[1] Shulgin reports that 7 of the 9 mice injected with MME died as a result.[1] After describing his experiment, Shulgin speculates that MME may have an LD50 value of around 60–80 mg/Kg in mice when injected.[1] Shulgin describes that one of the mice began convulsing after being administered MME: "[...] the mouse went into a twitching series of convulsions (known as clonic in the trade) and in five minutes he was dead." The convulsions Shulgin noted may have been a sympom of serotonin syndrome in the mouse due to MME's affinity towards serotonin transporter in Mus musculus.[3]
Computational modeling predicts that MME has an LD50 of 330 mg/Kg. MME is also predicted to be neurotoxic (p=0.63), respiratorically toxic (p=0.69), carcinogenic (p=0.50), and ecotoxic (p=0.57). MME is predicted to cross the blood–brain barrier (p=0.79). [4]
ProTox-3.0's predictions about MME's toxicological properties.
Chemistry
[edit]MME has several isomers. MEM is one of them along with EMM. According to Alexander Shulgin EEM is not biologically active.[1] MEM is biologically active in humans and also possesses an affinity for the 5-HT2A receptor.[1][5]
Synthesis
[edit]Shulgin describes the synthesis of MME in his book PiHKAL. Shulgin starts with 4-ethoxy-3-methoxybenzaldehyde. Shulgin labels the 4-ethoxy-3-methoxybenzaldehyde as ethylvanillin, although ethylvanillin is in fact 3-ethoxy-4-hydroxybenzaldehyde. Ethylvanillin can be methylate to 4-ethoxy-3-methoxybenzladehyde. The 4-ethoxy-3-methoxybenzaldehyde is then subjected to a Bayer-Villiger oxidation with peracetic acid and acetic acid to yield 4-ethoxy-3-methoxyphenol. The 4-ethoxy-3-methoxyphenol is methylated to yield 2,4-dimethoxy-1-ethoxybenzene. The 2,4-dimethoxy-1-ethoxybenzene is subjected to Reimer-Tiemann formylated to 2,4-dimethoxy-5-ethoxybenzaldehyde. The 2,4-dimethoxy-5-ethoxybenzaldehyde by subjecting it to a Knoevenagel condensation with acetic acid, ammonium acetate and nitroethane, and reducing the resulting 1-(2,4-dimethoxy-5-ethoxyphenyl)-2-nitropropene to MME with lithium aluminium hydride under an inert atmosphere.[1]
See also
[edit]References
[edit]- ^ a b c d e f g MEM entry in PiHKAL
- ^ 1-(5-Ethoxy-2,4-dimethoxyphenyl)propan-2-amine, National Library of Medicine, PubChem, 3.1.2025. https://pubchem.ncbi.nlm.nih.gov/compound/44719602
- ^ Haberzettl R, Bert B, Fink H, Fox MA (November 2013). "Animal models of the serotonin syndrome: a systematic review". Behavioural Brain Research. 256: 328–345. doi:10.1016/j.bbr.2013.08.045. PMID 24004848.
- ^ Banerjee P, Kemmler E, Dunkel M, Preissner R (July 2024). "ProTox 3.0: a webserver for the prediction of toxicity of chemicals". Nucleic Acids Research. 52 (W1): W513 – W520. doi:10.1093/nar/gkae303. PMC 11223834. PMID 38647086.
- ^ 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.
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