2C-TFM is a psychedelic phenethylamine of the

2C family 2C (2C-''x'') is a general name for the family of psychedelic drug, psychedelic phenethylamines containing Methoxy, methoxy groups on the 2 and 5 carbon, positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the ...

. It was first synthesized in the laboratory of David E. Nichols. It has also been called 2C-CF₃, a name derived from the Para-trifluoromethyl group it contains.

Chemistry

2C-TFM is a code that represents 4-tri

fluoro Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely react ...

methyl-2,5-di

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

phenethylamine. The full name of the chemical is 2- ,5-dimethoxy-4-(trifluoromethyl)phenylthanamine.

Dosage

A psychedelic dosage of 2C-TFM is reported to be 3–5 mg.

Effects

Very little data exists, but some reports suggest 2C-TFM produces psychedelic (hallucinogenic/entheogenic) effects that last between 5 and 7 hours. It is considered to be the strongest 2C variation.

Legality

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 in ...

because of its structural similarities to

2C-B 2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book '' PiHKAL'', the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is so ...

and

2C-T-7 2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic ef ...

. However, 2C-TFM, unlike many other phenethylamines, has not been widely sold by internet retailers. In the wake of

Operation Web Tryp Operation Web Tryp was a United States Drug Enforcement Administration operation that ended on July 21, 2004 with the arrests of 10 persons. Its purpose was to investigate web sites suspected of distribution of unscheduled, unregulated tryptamines ...

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. 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.

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

tryptamines Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethy ...

and phenethylamines. 2C-TFM displaced radiolabelled ketanserin 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, in both ''in vitro'' studies and human trials.

Dangers

The toxicity of 2C-TFM is not known.

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.

References

{{Hallucinogenic phenethylamines 2C (psychedelics) Trifluoromethyl compounds Phenethylamines Methoxy compounds