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| Names | |
|---|---|
| Preferred IUPAC name 2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethan-1-amine | |
| Other names 2,5-Dimethoxy-4-(trifluoromethyl)phenethylamine | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| UNII | |
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| Properties | |
| C11H14F3NO2 | |
| Molar mass | 249.23 g/mol |
| Melting point | 260 °C (500 °F; 533 K) (hydrochloride)[1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
2C-TFM is apsychedelicphenethylamine of the2C family. It was first synthesized in the laboratory ofDavid E. Nichols. It has also been called2C-CF3, a name derived from thePara-trifluoromethyl group it contains.
2C-TFM is a code that represents4-trifluoromethyl-2,5-dimethoxyphenethylamine. The full name of the chemical is 2-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]ethanamine.
A psychedelic dosage of 2C-TFM is reported to be 3–5 mg.[2]
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.[2]
2C-TFM is unscheduled and uncontrolled in the United States, but possession and sales of 2C-TFM could potentially be prosecuted under theFederal Analog Act because of its structural similarities to2C-B and2C-T-7. However, 2C-TFM, unlike many otherphenethylamines, has not been widely sold by internet retailers. In the wake ofOperation 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 uniquepsychedelic. There have been no reported deaths or hospitalizations from 2C-TFM.
As of October 31st, 2016, 2C-TFM is a controlled substance (Schedule III) in Canada.[3]
The mechanism that produces the hallucinogenic and entheogenic effects of 2C-TFM is most likely to result from action as a5-HT2Aserotonin receptoragonist in the brain, a mechanism of action shared by all of the hallucinogenictryptamines andphenethylamines. 2C-TFM displaced radiolabelledketanserin 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 agonistDOI, indicating similar binding affinity at the receptor.[1] 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 andDOB, in bothin vitro studies and human trials.[2]
The toxicity of 2C-TFM is not known.
It is noted inThe 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."[4] The synthesis was published by Nichols and his research team.[1] 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.
