2,5-Dimethoxy-4-ethoxyamphetamine

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesizedbyAlexander Shulgin.^[1] In his book PiHKAL, he lists the active dose range as 20–50 mg, and the duration as 10–14 hours.^[1] According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.^[1]

2,5-Dimethoxy-4-ethoxyamphetamine

Legal status
Legal status	CA: Schedule I UK: Class B
Identifiers
IUPAC name 1-[(4-ethoxy-2,5-dimethoxy)phenyl]propan-2-amine
CAS Number	16128-88-4 Y
PubChem CID	542053
ChemSpider	472023 N
UNII	3I0ORO8174
ChEMBL	ChEMBL8225 N
CompTox Dashboard (EPA)	DTXSID00337348
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1cc(OC)c(cc1OC)CC(N)C)CC
InChI InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 N Key:ITZLAXJQDMGDEO-UHFFFAOYSA-N N
NY (what is this?)  (verify)

MEM possesses affinity (K_i) for the 5-HT_2A (3,948 nM), 5-HT_2B (64.5 nM), 5-HT₇ (7,156 nM), and σ₁ (5,077 nM) receptors. It behaves as a partial agonist at the 5-HT_2A receptor.^[2] MEM is relatively selective for these sites and displays low/negligible (> 10,000 nM) affinity for a wide array of other targets.^[2]

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