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MTFEM

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Not to be confused with MTF (male-to-female).

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=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

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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

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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

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MTFEM was first described in the scientific literature by Daniel Trachsel in 2012.[3][2] 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]

See also

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References

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  1. ^ a b c d e f g h i j 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. ^ a b c d e 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.
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