MME (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.
Pharmacology
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.[2]
Chemistry
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][3]
Synthesis
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]
