EEE (drug)

EEE
Clinical data
Other names2,4,5-Triethoxyamphetamine; TMA2-2,4,5-TriEtO; TMA2-TriEtO
Routes of
administration		Unknown
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown
Identifiers
  • 1-(2,4,5-triethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H25NO3
Molar mass267.369 g·mol−1
3D model (JSmol)
  • CCOc1cc(OCC)c(cc1OCC)CC(C)N
  • InChI=1S/C15H25NO3/c1-5-17-13-10-15(19-7-3)14(18-6-2)9-12(13)8-11(4)16/h9-11H,5-8,16H2,1-4H3 checkY
  • Key:PVOHHXSVHWUAMS-UHFFFAOYSA-N checkY
  (verify)

EEE, also known as 2,4,5-triethoxyamphetamine or as TMA2-2,4,5-TriEtO, is a chemical compound of the phenethylamine, amphetamine, and DOx families. It is the analogue of TMA-2 in which the three methoxy groups on the phenyl ring have been replaced with ethoxy groups. In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists EEE's dose and duration as unknown. Shulgin stated that EEE has never been tested in humans. The chemical synthesis of EEE has been described. EEE was first described in the scientific literature by Shulgin in 1968. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.

See also

References

  1. 1 2 3 4 5 6 7 8 Shulgin AT, Shulgin A (1991). "EEE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OL 22859055M.
  2. 1 2 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
  3. 1 2 3 4 Shulgin AT (January 1968). "The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine". J Med Chem. 11 (1): 186–187. doi:10.1021/jm00307a056. PMID 5637180. Archived from the original on 2025-07-12.
  4. 1 2 Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure–activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297. Archived from the original on 2025-07-12.