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 synthesized by Alexander 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
Identifiers
IUPAC name
  • 1-[(4-ethoxy-2,5-dimethoxy)phenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO3
Molar mass239.315 g·mol−1
3D model (JSmol)
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 (Ki) for the 5-HT2A (3,948 nM), 5-HT2B (64.5 nM), 5-HT7 (7,156 nM), and σ1 (5,077 nM) receptors. It behaves as a partial agonist at the 5-HT2A 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]

See also
  • 2,5-Dimethoxy-4-substituted amphetamines

References
  1. Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
  2. Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.


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