2C-TFM
IUPAC name 2,5-Dimethoxy-4-(trifluoromethyl)phenethylamine
Identifiers
CAS number	159277-08-4 Y
PubChem	10399795
ChemSpider	8575233 Y
ChEMBL	CHEMBL136354 Y
Jmol-3D images	Image 1
SMILES FC(F)(F)c1cc(OC)c(cc1OC)CCN
InChI InChI=1S/C11H14F3NO2/c1-16-9-6-8(11(12,13)14)10(17-2)5-7(9)3-4-15/h5-6H,3-4,15H2,1-2H3 Y Key: LYXGNMLWYONZID-UHFFFAOYSA-N Y InChI=1/C11H14F3NO2/c1-16-9-6-8(11(12,13)14)10(17-2)5-7(9)3-4-15/h5-6H,3-4,15H2,1-2H3 Key: LYXGNMLWYONZID-UHFFFAOYAE
Properties
Molecular formula	C11H14F3NO2
Molar mass	249.23 g/mol
Melting point	260 °C (hydrochloride)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

  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 may last 8–16 hours.

  Legality

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 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.

  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 and phenethylamines. 2C-TFM displaced radiolabelled ketanserin from 5-HT_2A/C receptors with a Ki of 74.5, as compared to a Ki of 80.9 for the more well known 5-HT_2A agonist DOI, 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 and DOB, in both in vitro studies and human trials.^[2]

  Dangers

The toxicity of 2C-TFM is not known.

  References

1. ^ Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Grudelsky GA, Nash JF (1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl-)2-aminopropane: A Potent Serotonin 5-HT2A/C agonist". J. Med. Chem. 37 (25): 4346–4351. DOI:10.1021/jm00051a011. PMID 7996545. 
2. ^ Trachsel, D. (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis: n/a. DOI:10.1002/dta.413.  edit