TFMFly

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TFMFly
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Clinical data
Other namesTFM-FLY; TFM-Fly; DOTFM-FLY
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
Legal status
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Illegal in Latvia
Identifiers
  • 1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-amine
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Chemical and physical data
FormulaC14H16F3NO2
Molar mass287.282 g·mol−1
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  • CC(CC1=C2CCOC2=C(C3=C1OCC3)C(F)(F)F)N
  • InChI=1S/C14H16F3NO2/c1-7(18)6-10-8-2-4-20-13(8)11(14(15,16)17)9-3-5-19-12(9)10/h7H,2-6,18H2,1H3
  • Key:KMWGSFWAZUVTCM-UHFFFAOYSA-N
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TFMFly, or TFM-FLY, also known as DOTFM-FLY, is a serotonin receptor modulator of the phenethylamine, amphetamine and DOx, and FLY families related to psychedelics like DOTFM and DOB-FLY.[1][2][3]

Pharmacology

Pharmacodynamics

It acts as a potent agonist at the 5HT2A serotonin receptor subtype, and is a chiral compound with the more active (R) enantiomer having a Ki of 0.12 nM at the human 5-HT2A receptor.[2] While the fully aromatic benzodifurans such as Bromo-DragonFLY generally have higher binding affinity than saturated compounds like 2C-B-FLY,[1] the saturated compounds have higher efficacy as agonists.[4]

Chemistry

Synthesis

The chemical synthesis of TFMFly has been described.[1]

Analogues

Analogues of TFMFly include DOTFM, DOB-FLY, and 25TFM-NBOMe, among others.

History

TFMFly was first reported by a team at Purdue University led by David E. Nichols in 2001.[1][3]

Society and culture

Latvia

TFMFly is illegal in Latvia.[5]

See also

References

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  1. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE (March 2001). "Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists". J Med Chem. 44 (6): 1003–1010. doi:10.1021/jm000491y. PMID 11300881.
  2. ^ a b Page Module:Citation/CS1/styles.css has no content.Parrish JC, Braden MR, Gundy E, Nichols DE (December 2005). "Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists". Journal of Neurochemistry. 95 (6): 1575–1584. doi:10.1111/j.1471-4159.2005.03477.x. PMID 16277614. S2CID 24005602.
  3. ^ a b Page Module:Citation/CS1/styles.css has no content.Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. Template:ProQuest.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Heim R. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Ph.D. thesis) (in German). Freien Universität Berlin.{{cite thesis}}: CS1 maint: unrecognized language (link)
  5. ^ Page Module:Citation/CS1/styles.css has no content."Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia] (in Latvian). Ministry of Health of the Republic of Latvia. Archived from the original on 2016-02-02. Retrieved 2015-10-15.{{cite web}}: CS1 maint: unrecognized language (link)

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