MTFEM

Clinical data
Other names	4-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)amphetamine
Drug class	Serotonin5-HT2 receptormodulator
ATC code	None
Identifiers
IUPAC name 1-[2,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]propan-2-amine
PubChemCID	172547198
Chemical and physical data
Formula	C13H18F3NO3
Molar mass	293.286 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(CC(N)C)c(cc1OCC(F)(F)F)OC
InChI 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 as4-(2,2,2-trifluoroethoxy)-2,5-dimethoxyamphetamine, is aserotonin receptor modulator of thephenethylamine,amphetamine, andDOx families.^[1] It is aderivative of the DOxpsychedelicsTMA-2 andMEM in which the 4-positionsubstituent has been extended.^[1] The drug is also the α-methyl or amphetamineanalogue of2C-O-22.^[1]

In humans, MTFEM producedstimulant effects at a dose of 2.5 mg and had aduration 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]

MTFEM acts as apotentmodulator of theserotonin5-HT₂ receptors.^[1] Itsaffinities (K_i) were 460 nM for the serotonin5-HT_2A receptor and 2,400 nM for the serotonin5-HT_2C receptor, whereas itsactivationalpotencies (EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy)) were 19 nM (80%) at the serotonin 5-HT_2A receptor and 200 nM (4.8%) at the serotonin5-HT_2B receptor.^[1] Hence, MTFEM is a near-full agonist of the serotonin 5-HT_2A receptor but a near-silent antagonist of the serotonin 5-HT_2B receptor.^[1] Besides the serotonin 5-HT₂ receptors, the drug showed little to no activity at various other assessedtargets, such as themonoamine transporters.^[1] It does not appear to have been tested for psychedelic-like activity in animals.^[1]

MTFEM was first described in thescientific literature byDaniel Trachsel in 2012.^[3][2] Itspsychoactive effects in humans were reported by Trachsel and colleagues in 2013.^[2] Subsequently, it was characterized in more detail by a group including Trachsel andMatthias Liechti in 2019.^[1] The compound's name is said to derive from itsbenzenering substituents, "methoxytrifluoroethoxymethoxy".^[1]

MTFEM is acontrolled substance inCanada under phenethylamine blanket-ban language.^[4]

• DOx (psychedelics)
• MEM § Derivatives

• MTFEM - Isomer Design

• Drugs not assigned an ATC code
• 5-HT2A agonists
• 5-HT2B antagonists
• Daniel Trachsel
• DOx (psychedelics)
• Psychedelic phenethylamines
• Trifluoromethyl compounds

• CS1 German-language sources (de)
• Articles with short description
• Short description matches Wikidata
• Chemical articles without CAS registry number
• Articles without EBI source
• Chemical pages without ChemSpiderID
• Chemical pages without DrugBank identifier
• Articles without KEGG source
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• Drugs with no legal status
• Articles containing unverified chemical infoboxes