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2C-TFM

From Wikipedia, the free encyclopedia
Psychedelic phenethylamine drug

Pharmaceutical compound
2C-TFM
Clinical data
Other names2C-CF3; 2,5-Dimethoxy-4-trifluoromethylphenethylamine; 4-Trifluoromethyl-2,5-dimethoxyphenethylamine
Routes of
administration		Oral
Drug classSerotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen
Pharmacokinetic data
Duration of action≥5–10 hours[1][2]
Identifiers
  • 2-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]ethan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H14F3NO2
Molar mass249.233 g·mol−1
3D model (JSmol)
Melting point260 °C (500 °F) (hydrochloride)[3]
  • FC(F)(C1=C(OC)C=C(CCN)C(OC)=C1)F
  • 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 checkY
  • Key:LYXGNMLWYONZID-UHFFFAOYSA-N checkY
  (verify)

2C-TFM, also known as4-trifluoromethyl-2,5-dimethoxyphenethylamine, is aserotonin5-HT2 receptoragonist andpsychedelic drug of thephenethylamine and2C families.[1][2] It has also been called2C-CF3, a name derived from thepara-trifluoromethyl group it contains. The drug was firstsynthesized in the laboratory ofDavid E. Nichols. Later, it was tried humans and its psychedelic effects were confirmed.[1] 2C-TFM is the mostpotent psychedelic of the 2C psychedelics, with an active dosage of 3 to 6 mgorally.[1][2]

Dosage and effects

[edit]

A psychedelicdosage of 2C-TFM has been reported byDaniel Trachsel andAlexander Shulgin to be 3 to 6 mg.[1][2] Itsduration has been reported by Trachsel to be 5 to 7 hours or 6 to 10 hours or more in different publications.[1][2] It is the most potent 2C variation.[1]

Pharmacology

[edit]

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.[3] 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.[1]

Dangers

[edit]

The toxicity of 2C-TFM is not known.

Chemistry

[edit]

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

[edit]

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.[3] 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

[edit]

United States

[edit]

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.

Canada

[edit]

As of October 31st, 2016, 2C-TFM is a controlled substance (Schedule III) in Canada.[5]

See also

[edit]

References

[edit]
  1. ^abcdefghTrachsel D (2012)."Fluorine in psychedelic phenethylamines".Drug Testing and Analysis.4 (7–8):577–590.doi:10.1002/dta.413.PMID 22374819. Archived fromthe original on 2013-12-12. Retrieved2013-12-09.The 4-trifluoromethyl derivative 2C-TFM (34) was identified as a potent 5-HT2A/C receptor agonist by Nichols et al. in 1994.[28] Together with its α-methyl congener DOTFM (35) it is among the most potent simple phenethylamines at these binding sites, showing comparable or slightly higher binding affinities than DOB (29) and DOI (30).[28] Compared to DOB (29) and DOI (30), both compounds 34 and 35 turned out to be of equal, or slightly increased potency in DD studies (rats, training drug: LSD).[28] Within the context of a DD study, this was the first time for a 2C derivative to be found equally potent to the potent 3C derivatives DOB (29) and DOI (30). In humans, initial experiments seem to be consistent with high potencies (34: 3–5 mg; 35: 0.3 mg or more. A.T. Shulgin, personal communication in 2003).[4]
  2. ^abcdeTrachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag.ISBN 978-3-03788-700-4.OCLC 858805226.
  3. ^abcNichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, et al. (December 1994)."1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist".Journal of Medicinal Chemistry.37 (25):4346–4351.doi:10.1021/jm00051a011.PMID 7996545. Archived fromthe original on 2014-02-02. Retrieved2015-08-29.
  4. ^Shulgin, Alexander T., Tania Manning, Paul F. Daley (2011).The Shulgin Index Volume One Psychedelic Phenethylamines and Related Compounds. Transform Press.ISBN 978-0-9630096-3-0.
  5. ^"Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)".Canada Gazette. Vol. 150, no. 9. 4 May 2016.
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