TFMBOX

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Not to be confused with BOx (psychedelics).
TFMBOX
Clinical data
Other names"Compound 5c"
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 7-methoxy-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzoxepin-4-amine
CAS Number
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC12H14F3NO2
Molar mass261.244 g·mol−1
3D model (JSmol)
  • COc1cc2CC(N)CCOc2cc1C(F)(F)F
  • InChI=1S/C12H14F3NO2/c1-17-11-5-7-4-8(16)2-3-18-10(7)6-9(11)12(13,14)15/h5-6,8H,2-4,16H2,1H3
  • Key:NAOXZRLWFAOHAP-UHFFFAOYSA-N

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]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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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 (IC50Tooltip half-maximal inhibitory concentration = 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

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Analogues

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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]

History

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TFMBOX was first described in the scientific literature by Nick Cozzi, a student of David E. Nichols, by 1994.[2][3]

See also

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References

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