TFMBOX
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
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| Clinical data | |
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| Other names | "Compound 5c" |
| Drug class | Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen |
| Identifiers | |
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| Chemical and physical data | |
| Formula | C12H14F3NO2 |
| Molar mass | 261.244 g·mol−1 |
| 3D model (JSmol) | |
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Interactions
Pharmacology
Pharmacodynamics
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]
Chemistry
Analogues
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).[2][3] However, BBOX and IBOX only partially substituted for LSD in drug discrimination tests.[2][3][4]
TFMBOX
BBOX
IBOX
History
TFMBOX was first described in the scientific literature by Nick Cozzi, a student of David E. Nichols, by 1994.[2][3]