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Names

DOB-FLY
B-FLY
1-(8-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)propan-2-amine

IUPAC name

1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl)propan-2-amine

ID 2023 · Formula C₁₃H₁₆BrNO₂ · Molecular weight 298.176

InChI 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

InChI Key FKRREVSELFOLDT-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CC(Cc1c2OCCc2c(c2c1CCO2)Br)N

ChemSpider 8193127
PubChem 10017554
Wikidata Q82248650
Wikipedia, see Substituted benzofuran

Shulgin Index #10 B-DFLY · Table 7Page 356Row 19

Phenethylamine: Von der Strucktur zur Funktion DOB-FLY: 8.4 (47) 700, 701 · 8.5 (389) 853, 854, 855, 856, 857, 858, 860, 861 · 8.6 (80) 891

Monte, AP; Marona-Lewicka, D; Parker, MA; Wainscott, DB; Nelson, DL; Nichols, DE. Dihydrobenzofuran analogues of hallucinogens. 3. 1 Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups J. Med. Chem., 1 Jan 1996, 39 (15), 2953–2961. 290 kB. https://doi.org/10.1021/jm960199j #7b

Braden, MR. Towards a biophysical understanding of hallucinogen action Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #DOB-FLY

Parker, MA; Marona-Lewicka, D; Lucaites, VL; Nelson, DL; Nichols, DE. A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT_2A receptor J. Med. Chem., 1 Dec 1998, 41 (26), 5148–5149. 382 kB. https://doi.org/10.1021/jm9803525 #2 NMR

Chambers, JJ; Kurrasch-Orbaugh, DM; Parker, MA; Nichols, DE. Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT_2A/2C receptor agonists J. Med. Chem., 1 Mar 2001, 44 (6), 1003–1010. 337 kB. https://doi.org/10.1021/jm000491y #5b NMR

Heim, R. Synthesis and pharmacology of potent 5-HT_2A receptor agonists with N-2-methoxybenzyl partial structure SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #249 In German. MS,NMR,IR

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT_2A receptors ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. https://doi.org/10.1002/cmdc.200800133 #39

Whiteside, MS; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Nichols, DE; Monte, A. Substituted hexahydrobenzodipyrans as 5-HT_2A/2C receptor probes Bioorg. Med. Chem., 1 Oct 2002, 10 (10), 3301–3306. 141 kB. https://doi.org/10.1016/S0968-0896(02)00209-2 #2b NMR

Zaitsu, K; Katagi, M; Kamata, H; Nakanishi, K; Shima, N; Kamata, T; Nishioka, H; Miki, A; Tatsuno, M; Tsuchichashi, H. Simultaneous analysis of six novel hallucinogenic (tetrahydrobenzodifuranyl)aminoalkanes (FLYs) and (benzodifuranyl)aminoalkanes (DragonFLYs) by GC-MS, LC-MS, and LC-MS-MS Forensic Toxicol., 1 Jan 2010, 24 (1), 9–18. 570 kB. https://doi.org/10.1007/s11419-009-0083-0 GC,LC,MS

Fenderson5555. Two syntheses of bromo-dragonFLY , 15 Dec 2012. . Fenderson5555 9.8 MB.

Schultz, DM. Synthesis of serotonin agonists as 5-HT_2A and 5-HT_2C receptor molecular probes UW-LaCrosseJUR, 1 Jan 2006, 9, 1–6. 117 kB. #2

May, EJ. Synthesis of mixed heterocyclic phenylethylamines as serotonin receptor probes UW-LaCrosseJUR, 1 Jan 2002, 5, 391–398. 311 kB. #1

Whiteside, MS. Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT_2A/2C receptor probes UW-LaCrosseJUR, 1 Jan 1999, 2, 61–68. 272 kB. #3b NMR,IR

Reed, EC; Kiddon, GS. The characterization of three FLY compounds (2C-B-FLY, 3C-B-FLY, and Bromo-DragonFLY) Microgram J., 1 Jan 2007, 5 (1–4), 26–33. 112 kB. #3C-B-FLY GC,MS,NMR,IR

Feng, Z; Mohapatra, S; Klimko, PG; Hellberg, MR; May, JA; Kelly, C; Williams, G; McLaughlin, MA; Sharif, NA. Novel benzodifuran analogs as potent 5-HT_2A receptor agonists with ocular hypotensive activity Bioorg. Med. Chem. Lett., 1 Jun 2007, 17 (11), 2998–3002. 163 kB. https://doi.org/10.1016/j.bmcl.2007.03.073 #1

Isberg, V; Paine, J; Leth-Petersen, S; Kristensen, JL; Gloriam, DE. Structure-activity relationships of constrained phenylethylamine ligands for the serotonin 5-HT₂ receptors PLoS ONE, 7 Nov 2013, 8 (11), e78515. 2.3 MB. https://doi.org/10.1371/journal.pone.0078515 #2b MS,NMR

Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products Drug Test. Anal., 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315

Nichols, DE. Chemistry and structure–activity relationships of psychedelics In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #52

Nichols, DE. Structure-activity relationships of serotonin 5-HT_2A agonists WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42 #50

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT_2A receptor ligands Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. https://doi.org/10.1016/j.bmc.2008.02.033 #2

McCorvy, JD. Mapping the binding site of the 5-HT_2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #Br-Fly

Monte, AP. Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Aug 1995. 10.7 MB. #9 MS,NMR

Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #DOB-FLY

Wallach, J; Cao, AB; Calkins, MM; Heim, AJ; Lanham, JK; Bonniwell, EM; Hennessey, JJ; Bock, HA; Anderson, EI; Sherwood, AM; Morris, H; de Klein, R; Klein, AK; Cuccurazzu, B; Gamrat, J; Fannana, T; Zauhar, R; Halberstadt, AL; McCorvy, JD. Identification of 5-HT_2A receptor signaling pathways responsible for psychedelic potential bioRxiv, 31 Jul 2023, 2023.07.29.551106. 9.8 MB. https://doi.org/10.1101/2023.07.29.551106 #3C-B-FLY LC,MS,NMR

Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT_2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #100

2C-B-5-hemiFLY-β6

BE

BBat

2C-B-GNAT

2C-B-FLEA

7 Dec 2019 · · Isomer Design