Article · Wikipedia archive · Last revised Jul 16, 2026

DOB-FLY

DOB-FLY, also known as 3C-B-FLY or as B-FLY, is a psychedelic drug and designer drug of the phenethylamine, amphetamine, DOx, and FLY families. It is the FLY derivative of DOB, the amphetamine (α-methyl) derivative of 2C-B-FLY, and the partially saturated analogue of Bromo-DragonFLY (DOB-DFLY).

Last revised
Jul 16, 2026
Read time
≈ 2 min
Length
439 w
Citations
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Source
Wikipedia ↗
DOB-FLY
Clinical data
Other names3C-B-FLY; B-FLY; Bromo-FLY
Routes of
administration		Oral
Drug classSerotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • In general unscheduled
Identifiers
  • 1-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H16BrNO2
Molar mass298.180 g·mol−1
3D model (JSmol)
  • CC(CC1=C2CCOC2=C(C3=C1OCC3)Br)N
  • InChI=1S/C13H16BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h7H,2-6,15H2,1H3
  • Key:FKRREVSELFOLDT-UHFFFAOYSA-N

DOB-FLY, also known as 3C-B-FLY or as B-FLY, is a psychedelic drug and designer drug of the phenethylamine, amphetamine, DOx, and FLY families. It is the FLY derivative of DOB, the amphetamine (α-methyl) derivative of 2C-B-FLY, and the partially saturated analogue of Bromo-DragonFLY (DOB-DFLY).

Unlike Bromo-DragonFLY, DOB-FLY is only slightly more potent than DOB itself, with an active dose in humans of around 1 mg orally (compared to 1–3 mg orally for DOB).123456

Analogues of DOB-FLY include DOB, 2C-B-FLY, Bromo-DragonFLY (DOB-DFLY), TFMFly (TFM-FLY), and DOB-5-hemiFLY, among others.

DOB-FLY was developed by David E. Nichols and colleagues at Purdue University. It is a controlled substance in Canada under phenethylamine blanket-ban language,7 but is not explicitly controlled in the United States.8

See also

See also

References

References

  1. Parker MA, Marona-Lewicka D, Lucaites VL, Nelson DL, Nichols DE (December 1998). "A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor". Journal of Medicinal Chemistry. 41 (26): 5148–9. doi:10.1021/jm9803525. PMID 9857084.
  2. Feng Z, Mohapatra S, Klimko PG, Hellberg MR, May JA, Kelly C, et al. (June 2007). "Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity". Bioorganic & Medicinal Chemistry Letters. 17 (11): 2998–3002. doi:10.1016/j.bmcl.2007.03.073. PMID 17419053.
  3. Parker MA, Kurrasch DM, Nichols DE (April 2008). "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry. 16 (8): 4661–9. doi:10.1016/j.bmc.2008.02.033. PMC 2442558. PMID 18296055.
  4. Schultz DM, Prescher JA, Kidd S, Marona-Lewicka D, Nichols DE, Monte A (June 2008). "'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines". Bioorganic & Medicinal Chemistry. 16 (11): 6242–51. doi:10.1016/j.bmc.2008.04.030. PMC 2601679. PMID 18467103.
  5. Zaitsu K, Katagi M, Kamata H, Nakanishi K, Shima N, Kamata T, et al. (January 2010). "Simultaneous analysis of six novel hallucinogenic (tetrahydrobenzodifuranyl) aminoalkanes (FLYs) and (benzodifuranyl) aminoalkanes (DragonFLYs) by GC-MS, LC-MS, and LC-MS-MS". Forensic Toxicology. 28 (1): 9–18. doi:10.1007/s11419-009-0083-0. S2CID 24100422.
  6. 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.
  7. "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  8. Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
External links