2C-TFM

Use and effects

A psychedelic dose of 2C-TFM has been reported by Daniel Trachsel and Alexander Shulgin 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.

Interactions

Pharmacology

Pharmacodynamics

The mechanism that produces the hallucinogenic and entheogenic effects of 2C-TFM is most likely to result from action as a 5-HT2A serotonin receptor agonist in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines. 2C-TFM displaced radiolabelled ketanserin from 5-HT2A/C receptors with a Ki of 74.5 nM, as compared to a Ki of 80.9 nM for the more well known 5-HT2A 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.

Chemistry

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

Synthesis

The chemical synthesis of 2C-TFM has been described. In The Shulgin Index Volume 1: Psychedelic Phenethylamines and Related Compounds, 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.

Analogues and derivatives

Analogues and derivatives of 2C-TFM include 2C-TFE, 2C-T-TFM (2C-T-36; CYB210010), DOTFM, 4C-TFM, 25TFM-NBOMe, LPH-5 ((S)-2C-TFM-3PIP), and 2T-2CTFM-3PIP, among others.

Society and culture

Legal status

Canada

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

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 if intended for human consumption because of its structural similarities to 2C-B and 2C-T-7. However, 2C-TFM, unlike many other phenethylamines, 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. There have been no reported deaths or hospitalizations from 2C-TFM.

References

References

1. (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
2. (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis.
3. (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". [[Transform Press]].
4. (2011). "[[The Shulgin Index". Transform Press.
5. (December 1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist". Journal of Medicinal Chemistry.
6. (4 May 2016). "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)".
7. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.