2C-TFM: Difference between revisions
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==Synthesis== |
==Synthesis== |
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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."<ref>{{cite book|last=Shulgin|first=Alexander T., Tania Manning, Paul F. Daley|title=The Shulgin Index Volume One Psychedelic Phenethylamines and Related Compounds|year=2011|publisher=Transform Press|isbn=9780963009630}}</ref> The synthesis was published by Nichols and his research team.<ref>{{cite journal | author = Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Grudelsky GA, Nash JF | title = 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl-)2-aminopropane: A Potent Serotonin 5-HT2A/C agonist | journal = J. Med. Chem. | year = 1994 | volume = 37 | pages = 4346–4351 | doi = 10.1021/jm00051a011 | pmid = 7996545 | issue = 25}}</ref> |
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==References== |
==References== |
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Revision as of 04:29, 15 November 2013
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| Names | |
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| IUPAC name
2,5-Dimethoxy-4-(trifluoromethyl)phenethylamine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C11H14F3NO2 | |
| Molar mass | 249.23 g/mol |
| Melting point | 260 °C (hydrochloride) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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-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 74.5nM, as compared to a Ki of 80.9nM for the more well known 5-HT2A 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.
Synthesis
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."[3] The synthesis was published by Nichols and his research team.[4]
References
- ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/dta.413, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1002/dta.413instead. - ^ Shulgin, Alexander T., Tania Manning, Paul F. Daley (2011). The Shulgin Index Volume One Psychedelic Phenethylamines and Related Compounds. Transform Press. ISBN 9780963009630.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link)