MTFEM, also known as 4-(2,2,2-trifluoroethoxy)-2,5-dimethoxyamphetamine, is a

serotonin receptor modulator 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, and

DOx 4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- positio ...

families. It is a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

of the DOx

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

s TMA-2 and

MEM Mem (also spelled Meem, Meme, or Mim) is the thirteenth letter of the Semitic abjads, including Hebrew ''mēm'' , Aramaic ''mem'' 𐡌, Syriac ''mīm'' ܡ, Arabic ''mīm'' , and Phoenician ''mēm'' 𐤌. Its sound value is . It is also relate ...

in which the 4-position

substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...

has been extended. The drug is also the α-

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

or amphetamine analogue of 2C-O-22.

Use and effects

In humans, MTFEM produced

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

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

Pharmacology

MTFEM acts as a potent

modulator Signal modulation is the process of varying one or more properties of a periodic waveform in electronics and telecommunication for the purpose of transmitting information. The process encodes information in form of the modulation or message ...

of the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT₂ receptors. Its affinities (K_i) were 460nM for the serotonin 5-HT_2A receptor and 2,400nM for the serotonin 5-HT_2C receptor, whereas its activational potencies ( ()) were 19nM (80%) at the serotonin 5-HT_2A receptor and 200nM (4.8%) at the serotonin 5-HT_2B receptor. Hence, MTFEM is a near-

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...

of the serotonin 5-HT_2A receptor but a near-

silent antagonist A receptor antagonist is a type of receptor ligand or drug that blocks or dampens a biological response by binding to and blocking a receptor rather than activating it like an agonist. Antagonist drugs interfere in the natural operation of recep ...

of the serotonin 5-HT_2B receptor. Besides the serotonin 5-HT₂ receptors, the drug showed little to no activity at various other assessed

target Target may refer to: Warfare and shooting * Shooting target, used in marksmanship training and various shooting sports ** Bullseye (target), the goal one for which one aims in many of these sports ** Aiming point, in field artille ...

s, such as the

monoamine transporter Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...

s. It does not appear to have been tested for psychedelic-like activity in animals.

History

MTFEM was first described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

Daniel Trachsel Daniel Trachsel is a Swiss people, Swiss chemist who studies psychedelic drug, psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen chemical compound, compounds, including their psycho ...

in 2012. Its

psychoactive A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

effects in humans were reported by Trachsel and colleagues in 2013. Subsequently, it was characterized in more detail by a group including Trachsel and

Matthias Liechti Matthias Emanuel Liechti (born 27 May 1970) is a Swiss scientist and physician who studies psychedelics, entactogens, and other psychoactive drugs. He is the head of the Liechti Lab at the University of Basel in Switzerland. The lab conducts '' ...

in 2019. The compound's name is said to derive from its

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

ring (The) Ring(s) may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell Arts, entertainment, and media Film and TV * ''The Ring'' (franchise), a ...

substituents, "''m''ethoxy ''t''ri''f''luoro''e''thoxy ''m''ethoxy".

References

External links

MTFEM - Isomer Design
{{Phenethylamines 2,5-Dimethoxyphenethylamines 5-HT2A agonists 5-HT2B antagonists DOx (psychedelics) Psychedelic phenethylamines Trifluoromethyl compounds

Use and effects

Pharmacology

History

See also

References

External links