• 1-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
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

DOB-FLY is a recreational designer drug with psychedelic effects. It can be regarded as the alpha-methyl derivative of 2C-B-FLY or the partially saturated counterpart of bromo-dragonfly. Unlike bromo-dragonfly, DOB-FLY is only slightly more potent than DOB itself, with an active dose in humans of around 1 mg.[1][2][3][4][5][6]

See also


  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.