Chemistry:TFMBOX

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TFMBOX is a putative serotonergic psychedelic of the phenethylamine and benzoxepin ("BOX") families.[1][2][3] It is the cyclized phenethylamine analogue of DOTFM and 2C-TFM in which the α carbon has been connected to the 2-methoxy group via an ethyl chain to form a benzoxepin ring system.[1][2]

The drug was assessed at and showed affinity for the serotonin 5-HT2A and 5-HT1A receptors, with Ki values of 340 nM and 1,300 nM, respectively.[2] Its affinity for the serotonin 5-HT2A receptor was about 15-fold lower than that of DOB and DOI, whereas its affinity for the serotonin 5-HT1A receptor was the same as that of DOI and was about half that of DOB.[2] TFMBOX also very weakly inhibited the reuptake of serotonin (IC50 = 9,900 nM), but did not affect dopamine or norepinephrine reuptake (IC50 = >50,000–100,000 nM).[2] The drug fully substituted for LSD in rodent drug discrimination tests, albeit with about one-third of the potency of DOB and 2C-B.[2]

TFMBOX was first described in the scientific literature by Nick Cozzi, a student of David E. Nichols, by 1994.[2][3] Other "BOX" drugs that were assessed by the group include BOX (the cyclized analogue of 2C-H and DOH), BBOX (the cyclized analogue of 2C-B and DOB), and IBOX (the cyclized analogue of 2C-I and DOI).[2][3] However, BBOX and IBOX only partially substituted for LSD in drug discrimination tests.[2][3][4]

See also

References

  1. ↑ 1.0 1.1 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 852–853. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. Retrieved 31 January 2025. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 "Conformationally Restricted Tetrahydro-1-Benzoxepin Analogs of Hallucinogenic Phenethylamines". Medicinal Chemistry Research 5 (651–663). 1995. https://bitnest.netfirms.com/external/Med.Chem.Res/5..651. 
  3. ↑ 3.0 3.1 3.2 3.3 Cozzi NV (1994). Pharmacological studies of some psychoactive phenylalkylamines: Entactogens, hallucinogens, and anorectics (Ph.D. thesis). University of Wisconsin, Madison. . Retrieved 15 April 2025.
  4. ↑ Monte AP (August 1995). Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines (Ph.D. thesis). Purdue University. . Retrieved 15 April 2025.

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