MME (psychedelic)

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]

MME

Names
Preferred IUPAC name 1-(5-Ethoxy-2,4-dimethoxyphenyl)propan-2-amine
Other names 2,4-Dimethoxy-5-ethoxyamphetamine
Identifiers
CAS Number	23693-32-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3244455
ChemSpider	21106338 Y
PubChem CID	44719602
UNII	9KL74SEV4U
CompTox Dashboard (EPA)	DTXSID90660374
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 InChI=1/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 Key: NAMNXRTWJMASNT-UHFFFAOYAR
SMILES COc1cc(OC)c(cc1OCC)CC(C)N
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

Pharmacology and toxicology

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

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-HT_2A receptor.^[1][5]

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]

See also

• Phenethylamine
• Psychedelics, dissociatives and deliriants