MME (drug)

MME, also known as 2,4-dimethoxy-5-ethoxyamphetamine or as TMA2-5-EtO, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families related to TMA-2.^[1] It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with an ethoxy group.^[1]

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MME's dose as 40 mg and above orally and its duration as probably 6 to 10 hours.^[1] MME received a "plus-two" rating on the Shulgin Rating Scale.^[1] However, its specific effects were not described, aside from diarrhea and beyond statements like it having "a possibly interesting collection of effects" and it being "very encouraging".^[1] Moreover, Shulgin stated that it was less active than MEM, another related TMA-2 analogue.^[1] Shulgin expressed interest in further evaluating higher doses of MME.^[1]

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]

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 Baeyer–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]

MME has several isomers.^[1] MEM is one of them along with EMM.^[1] According to Alexander Shulgin, EEM is not active.^[1] MEM is active in humans and also possesses activity at the serotonin 5-HT_2A receptor.^[1][2] Other analogues of MME include Iris (DOM-5-EtO) and metaescaline.^[1]

MME was first described in the scientific literature by Alexander Shulgin in 1968.^[3] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.^[1]

• DOx (psychedelics)
• TWEETIO § DOx compounds
• EMM and MEM

• MME - Isomer Design
• MME - PiHKAL - Erowid
• MME - PiHKAL - Isomer Design