2C-TFM

A psychedelic dosage of 2C-TFM has been reported by Daniel Trachsel and Alexander Shulgin to be 3 to 6{{nbsp}}mg. Its duration has been reported by Trachsel to be 5 to 7{{nbsp}}hours or 6 to 10{{nbsp}}hours or more in different publications. It is the most potent 2C variation.

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 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.{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Testing and Analysis | volume = 4 | issue = 7–8 | pages = 577–590 | year = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 | url = http://bitnest.ca/external.php?id=%257DbxUgXXCNAUj%257E%257E%2507 | access-date = 2013-12-09 | quote = 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] | archive-url = https://web.archive.org/web/20131212071801/http://bitnest.ca/external.php?id=%257DbxUgXXCNAUj%257E%257E%2507 | archive-date = 2013-12-12 | url-access = subscription }}

The toxicity of 2C-TFM is not known.

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.

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."{{cite book |author=Shulgin, Alexander T. |author2=Tania Manning |author3=Paul F. Daley |title=The Shulgin Index Volume One Psychedelic Phenethylamines and Related Compounds|year=2011|publisher=Transform Press|isbn=978-0-9630096-3-0}} The synthesis was published by Nichols and his research team.{{cite journal | vauthors = Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, Nash JF | title = 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist | journal = Journal of Medicinal Chemistry | volume = 37 | issue = 25 | pages = 4346–4351 | date = December 1994 | pmid = 7996545 | doi = 10.1021/jm00051a011 | url = http://bitnest.ca/external.php?id=%257DbxUgZ%255BC%2540X%2504tzz%2505TWZP | access-date = 2015-08-29 | archive-url = https://web.archive.org/web/20140202182547/http://bitnest.ca/external.php?id=%257DbxUgZ%255BC%2540X%2504tzz%2505TWZP | archive-date = 2014-02-02 | url-access = subscription }} 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.

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.

As of October 31st, 2016, 2C-TFM is a controlled substance (Schedule III) in Canada.{{cite periodical |url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php |periodical=Canada Gazette |volume=150 |issue=9 |title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) | date=4 May 2016 }}

• 2C-T-TFM (2C-T-36; CYB210010)
• 25TFM-NBOMe
• LPH-5
• TCB-2
• ZC-B

{{Reflist}}

{{Psychedelics}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

Category:5-HT2A agonists

Category:5-HT2C agonists

Category:2C (psychedelics)

Category:2,5-Dimethoxyphenethylamines

Category:Psychedelic phenethylamines

Category:Trifluoromethyl compounds