TFMBOX is a putative serotonergic psychedelic of the phenethylamine and benzoxepin ("BOX") families. It is the cyclized phenethylamine analogue of DOTFM and 2C-TFM in which the ñ carbon has been connected to the 2-methoxy group via an ethyl chain to form a benzoxepin ring system.
The drug was assessed at and showed affinity for the serotonin 5-HT<sub>2A</sub> and 5-HT<sub>1A</sub> receptors, with K<sub>i</sub> values of 340nM and 1,300nM, respectively. Its affinity for the serotonin 5-HT<sub>2A</sub> receptor was about 15-fold lower than that of DOB and DOI, whereas its affinity for the serotonin 5-HT<sub>1A</sub> receptor was the same as that of DOI and was about half that of DOB. TFMBOX also very weakly inhibited the reuptake of serotonin ( = 9,900nM), but did not affect dopamine or norepinephrine reuptake ( = >50,000âÂÂ100,000nM). The drug fully substituted for LSD in rodent drug discrimination tests, albeit with about one-third of the potency of DOB and 2C-B.
Other "BOX" drugs that have been assessed 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). However, BBOX and IBOX only partially substituted for LSD in drug discrimination tests.
TFMBOX was first described in the scientific literature by Nick Cozzi, a student of David E. Nichols, by 1994.