2C-TFM, also known as 4-trifluoromethyl-2,5-dimethoxyphenethylamine, is a

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 receptor

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

and

psychedelic drug 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 halluc ...

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 ...

and 2C families. It has also been called 2C-CF₃, a name derived from the '' para''-trifluoromethyl group it contains. The drug was first synthesized in the laboratory of David E. Nichols. Later, it was tried humans and its psychedelic effects were confirmed. 2C-TFM is the most potent psychedelic of the 2C psychedelics, with an active dosage of 3 to 6mg orally.

Dosage and effects

A psychedelic dosage of 2C-TFM has been reported by

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 ...

and

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

to be 3 to 6mg. Its duration has been reported by Trachsel to be 5 to 7hours or 6 to 10hours or more in different publications. It is the most potent 2C variation.

Pharmacology

The mechanism that produces the hallucinogenic and entheogenic effects of 2C-TFM is most likely to result from action as a 5-HT_2A

serotonin receptor 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 ...

in the brain, a mechanism of action shared by all of the hallucinogenic

tryptamines Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...

and

phenethylamines Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative (chemistry), derivative compounds of phenethylamine ...

. 2C-TFM displaced radiolabelled

ketanserin Ketanserin, sold under the brand name Sufrexal, is an antihypertensive agent which is used to treat arterial hypertension and vasospasm, vasospastic disorders. It is also used in scientific research as an antiserotonergic medication, agent in th ...

from 5-HT_2A/C receptors with a K_i of 74.5 nM, as compared to a K_i of 80.9 nM for the more well known 5-HT_2A agonist DOI, indicating similar binding affinity at the receptor. The high binding affinity conferred by the 4-trifluoromethyl group is demonstrated by the fact that 2C-TFM is one of the only simple phenethylamines to rival the potency of psychedelic amphetamines like DOI and

DOB DOB or Dob often refers to date of birth. DOB or Dob may also refer to: Biochemistry * 2,5-dimethoxy-4-bromoamphetamine, Bromo-DMA, a psychedelic drug ** Meta-DOB, related substance ** Methyl-DOB, related substance * HLA-DOB, human gene Organiz ...

, in both ''in vitro'' studies and human trials.

Dangers

The toxicity of 2C-TFM is not known.

Chemistry

2C-TFM is a code that represents 4-trifluoromethyl-2,5-dimethoxyphenethylamine. The full name of the chemical is 2- ,5-dimethoxy-4-(trifluoromethyl)phenylthanamine.

Synthesis

It is noted in '' The Shulgin Index Volume 1: Psychedelic Phenethylamines and Related Compounds'' where the synthesis is written "from 2C-I (with trifluoroacetic anhydride) to 1-(2,5-dimethoxy-4-iodophenyl)-2-(trifluoroacetamido)ethane; (with methyl chlorodifluoroacetate, KF, Cul) to 1-(2,5-dimethoxy-4-trifluoromethylphenyl)-2-(trifluoroacetamido)ethane; (with KOH) to 2C-TFM." The synthesis was published by Nichols and his research team. Since 2C-TFM is usually synthesised from 2C-I and the reaction does not generally consume all of the starting material, samples of 2C-TFM are likely to be contaminated with detectable traces of unreacted 2C-I, which may pose legal issues in jurisdictions where 2C-I is illegal, even though 2C-TFM itself may not be prohibited.

Legal status

United States

2C-TFM is unscheduled and uncontrolled in the United States, but possession and sales of 2C-TFM could potentially be prosecuted under the

Federal Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

because of its structural similarities to

2C-B 2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by the slang name Nexus, is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. It was first synthesized by Alexander Shulgin in 1974 for use in psychoth ...

and

2C-T-7 2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generall ...

. However, 2C-TFM, unlike many other

, has not been widely sold by internet retailers. In the wake of Operation Web Tryp in July 2004, the issue of possession and sales of 2C-TFM and other similar chemicals will probably be resolved in the courtroom as well the fate of this rare but unique

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 ...

. There have been no reported deaths or hospitalizations from 2C-TFM.

Canada

As of October 31st, 2016, 2C-TFM is a controlled substance (Schedule III) in Canada.

References

{{Phenethylamines 5-HT2A agonists 5-HT2C agonists 2C (psychedelics) 2,5-Dimethoxyphenethylamines Psychedelic phenethylamines Trifluoromethyl compounds