MME (drug)

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]

MME

Clinical data
Other names	2,4-Dimethoxy-5-ethoxyamphetamine
Routes of administration	Oral[1]
ATC code	None
Pharmacokinetic data
Duration of action	6–10 hours[1]
Identifiers
IUPAC name 1-(5-ethoxy-2,4-dimethoxyphenyl)propan-2-amine
CAS Number	23693-32-5 Y
PubChem CID	44719602
ChemSpider	21106338 Y
UNII	9KL74SEV4U
ChEMBL	ChEMBL3244455
CompTox Dashboard (EPA)	DTXSID90660374
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(OC)c(cc1OCC)CC(C)N
InChI InChI=1S/C13H21NO3/c1-5-17-13-7-10(6-9(2)14)11(15-3)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3 Y Key:NAMNXRTWJMASNT-UHFFFAOYSA-N Y
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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]

ProTox-3.0's predictions about MME's toxicological properties.

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-HT_2A 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

• DOx (psychedelics)
• TWEETIO (psychedelics)