Article · Wikipedia archive · Last revised Jul 8, 2026

MTFEM

MTFEM, also known as 4-(2,2,2-trifluoroethoxy)-2,5-dimethoxyamphetamine, is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families. It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended. The drug is also the α-methyl or amphetamine analogue of 2C-O-22.

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MTFEM
Clinical data
Other names4-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)amphetamine
Drug classSerotonin 5-HT2 receptor modulator
ATC code
  • None
Identifiers
  • 1-[2,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]propan-2-amine
PubChem CID
Chemical and physical data
FormulaC13H18F3NO3
Molar mass293.286 g·mol−1
3D model (JSmol)
  • COc1cc(CC(N)C)c(cc1OCC(F)(F)F)OC
  • InChI=1S/C13H18F3NO3/c1-8(17)4-9-5-11(19-3)12(6-10(9)18-2)20-7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3
  • Key:LFPUPGGEYLURDG-UHFFFAOYSA-N

MTFEM, also known as 4-(2,2,2-trifluoroethoxy)-2,5-dimethoxyamphetamine, is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.1 It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended.1 The drug is also the α-methyl or amphetamine analogue of 2C-O-22.1

Use and effects

In humans, MTFEM produced stimulant effects at a dose of 2.5 mg and had a duration of 12 hours.2 Its full effects in humans were not determined and it was estimated that its human dose range would be 10 mg or more.2 Along with TMA-2 and MEM, it is one of the few compounds in its series tested and known to be active in humans.2

Pharmacology

Pharmacodynamics

MTFEM acts as a potent modulator of the serotonin 5-HT2 receptors.1 Its affinities (Ki) were 460 nM for the serotonin 5-HT2A receptor and 2,400 nM for the serotonin 5-HT2C receptor, whereas its activational potencies (EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy)) were 19 nM (80%) at the serotonin 5-HT2A receptor and 200 nM (4.8%) at the serotonin 5-HT2B receptor.1 Hence, MTFEM is a near-full agonist of the serotonin 5-HT2A receptor but a near-silent antagonist of the serotonin 5-HT2B receptor.1 Besides the serotonin 5-HT2 receptors, the drug showed little to no activity at various other assessed targets, such as the monoamine transporters.1 It does not appear to have been tested for psychedelic-like activity in animals.1

History

MTFEM was first described in the scientific literature by Daniel Trachsel in 2012.32 Its psychoactive effects in humans were reported by Trachsel and colleagues in 2013.2 Subsequently, it was characterized in more detail by a group including Trachsel and Matthias Liechti in 2019.1 The compound's name is said to derive from its benzene ring substituents, "methoxy trifluoroethoxy methoxy".1

Society and culture

Canada

MTFEM is a controlled substance in Canada under phenethylamine blanket-ban language.4

See also

See also

References

References

  1. Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Frontiers in Pharmacology. 10 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671.
  2. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 786–787. ISBN 978-3-03788-700-4. OCLC 858805226.
  3. Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  4. "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
External links