MME (drug)
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| Other names | 2,4-Dimethoxy-5-ethoxyamphetamine |
| Routes of administration | Oral[1] |
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| Duration of action | 6–10 hours[1] |
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| Formula | C13H21NO3 |
| Molar mass | 239.315 g·mol−1 |
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MME, also known as 2,4-dimethoxy-5-ethoxyamphetamine, is a lesser-known psychedelic drug.[1] It is a dimethoxy-ethoxy analogue of TMA-2.[1] MME was first synthesized by Alexander Shulgin.[1] In his book PiHKAL, the minimum dose is listed as 40 mg and above, and the duration listed as 6–10 hours.[1] MME received a plus-two rating on the Shulgin Rating Scale.[1]
Pharmacology
Alexander Shulgin describes in PiHKAL an experiment with MME, in which he administered 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."[1] The convulsions Shulgin noted may have been a symptom of serotonin syndrome in the mouse due to MME's affinity towards serotonin transporter in Mus musculus.[2]
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).[3]
Chemistry
MME has several isomers.[1] MEM is one of them along with EMM.[1] 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][4]
Synthesis
Shulgin describes the synthesis of MME in his book PiHKAL.[1] He starts with 4-ethoxy-3-methoxybenzaldehyde.[1] Shulgin labels the 4-ethoxy-3-methoxybenzaldehyde as ethylvanillin, although ethylvanillin is in fact 3-ethoxy-4-hydroxybenzaldehyde.[1] Ethylvanillin can be methylate to 4-ethoxy-3-methoxybenzladehyde.[1] 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.[1] The 4-ethoxy-3-methoxyphenol is methylated to yield 2,4-dimethoxy-1-ethoxybenzene.[1] The 2,4-dimethoxy-1-ethoxybenzene is subjected to Reimer-Tiemann formylated to 2,4-dimethoxy-5-ethoxybenzaldehyde.[1] 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
References
- ^ a b c d e f g h i j k l m n o p q r s t u v w Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. MME entry
- ^ 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.