TFMBOX

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 α 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_2A and 5-HT_1A receptors, with K_i values of 340 nM and 1,300 nM, respectively. Its affinity for the serotonin 5-HT_2A receptor was about 15-fold lower than that of DOB and DOI, whereas its affinity for the serotonin 5-HT_1A receptor was the same as that of DOI and was about half that of DOB. TFMBOX also very weakly inhibited the reuptake of serotonin (IC₅₀Tooltip half-maximal inhibitory concentration = 9,900 nM), but did not affect dopamine or norepinephrine reuptake (IC₅₀ = >50,000–100,000 nM). The drug fully substituted for LSD in rodent drug discrimination tests, albeit with about one-third of the potency of DOB and 2C-B.

TFMBOX was first described in the scientific literature by Nick Cozzi, a student of David E. Nichols, by 1994. 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). However, BBOX and IBOX only partially substituted for LSD in drug discrimination tests.