2C-I-FLY

2C-I-FLY
Clinical data
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(4-iodo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)ethanamine
PubChem CID
Chemical and physical data
FormulaC12H14INO2
Molar mass331.153 g·mol−1
3D model (JSmol)
  • C1COC2=C(C3=C(C(=C21)CCN)OCC3)I
  • InChI=1S/C12H14INO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2
  • Key:SDULYHWSVCNNAO-UHFFFAOYSA-N

2C-I-FLY is a psychedelic drug of the phenethylamine, 2C, and FLY families.[1][2] It is the FLY (benzodifuran) derivative of 2C-I and an analogue of 2C-B-FLY.[1][2] The monoamine oxidase (MAO) interactions of 2C-I-FLY have been described.[2] 2C-I-FLY produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[1] It showed about 3-fold lower potency than 2C-B-FLY and 2C-E-FLY in this assay, but was only slightly less potent than 2C-EF-FLY.[1] 2C-I-FLY was first described in the scientific literature by Lea Wagmann and colleagues in 2018 or 2019.[3][1][2]

See also

References

  1. ^ a b c d e Halberstadt AL, Chatha M, Stratford A, Grill M, Brandt SD (January 2019). "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology. 144: 368–376. doi:10.1016/j.neuropharm.2018.10.037. PMC 6863604. PMID 30385253.
  2. ^ a b c d Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Testing and Analysis. 11 (2): 318–324. doi:10.1002/dta.2494. PMID 30188017.
  3. ^ Wagmann L (2018). Psychoactive substances as substrates or inhibitors of enzymes in drug metabolism and transport (Ph.D. thesis). Universität Des Saarlandes. doi:10.22028/D291-27544. Retrieved 12 March 2026.
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