Article · Wikipedia archive · Last revised Aug 8, 2026

EMM (drug)

EMM, also known as 2-ethoxy-4,5-dimethoxyamphetamine or as TMA2-2-EtO, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to the psychedelic drug TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 2 position has been replaced with an ethoxy group. In his book PiHKAL and other publications, Alexander Shulgin lists EMM's dose as greater than 50 mg orally and its duration as unknown. The drug produced no effects at doses of up to 50 mg. Higher doses were not tested. The chemical synthesis of EMM has been described. EMM was first described in the scientific literature by Shulgin in 1968. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.

Last revised
Aug 8, 2026
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EMM
Clinical data
Other names2-Ethoxy-4,5-dimethoxyamphetamine; TMA2-2-EtO
Routes of
administration		Oral1
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown1
Identifiers
  • 1-(2,4,5-trimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO3
Molar mass239.315 g·mol−1
3D model (JSmol)
  • C1(=CC(=C(C=C1CC(C)N)OC)OC)OCC
  • InChI=1S/C13H21NO3/c1-5-17-11-8-13(16-4)12(15-3)7-10(11)6-9(2)14/h7-9H,5-6,14H2,1-4H3 checkY
  • Key:SKRNTJDDBVAEGB-UHFFFAOYSA-N checkY
  (verify)

EMM, also known as 2-ethoxy-4,5-dimethoxyamphetamine or as TMA2-2-EtO, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to the psychedelic drug TMA-2.123 It is the analogue of TMA-2 in which the methoxy group at the 2 position has been replaced with an ethoxy group.123 In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists EMM's dose as greater than 50 mg orally and its duration as unknown.123 The drug produced no effects at doses of up to 50 mg.12 Higher doses were not tested.123 The chemical synthesis of EMM has been described.14 EMM was first described in the scientific literature by Shulgin in 1968.4 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.1

See also

See also

References

References

  1. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. EMM Entry in PiHKAL
  2. Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.3.3. 2-Ethoxy-4,5-dimethoxyphenylisopropylamine The ortho-ethoxy homolog of TMA-2 (34) is 2-ethoxy-4,5-dimethoxyphenylisopropylamine (61, EMM, 2-ethoxy-4,5-dimethoxyamphetamine). Acute trials have been conducted to levels (30 mg of the hydrochloride salt, orally) more than twice those which precipitate threshold effects with either MEM (60) or TMA-2 (34) (Shulgin, 1968). No effects either central or peripheral were noted, indicating that EMM would be less than half as potent as these latter drugs as a psychotomimetic, if indeed it had that action at all.
  3. 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.
  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.
External links