Exploring DOB-dragonFLY. To explore a different substance…

Names:
DOB-dragonFLY · Bromo-dragonFLY · B-DFLY · 1-(8-Bromofuro[2,3-f][1]benzofuran-4-yl)propan-2-amine
IUPAC name:
1-(8-Bromobenzo[1,2-b:4,5-b′]difuran-4-yl)propan-2-amine
ID: 2033 · Formula: C13H12BrNO2 · Molecular weight: 294.144
InChI: InChI=1S/C13H12BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h2-5,7H,6,15H2,1H3

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. http://dx.doi.org/10.1002/cmdc.200800133

Parker, MA. Studies of perceptiotropic phenethylamines: Determinants of affinity for the 5-HT2A receptor. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 1998. 2.7 MB.

Huntington, BC. Synthesis and intermediate/by-product analysis of bromo-dragonfly, a dihydrobenzofuran analogue of phenethylamine hallucinogens. M. Sc. Thesis, University of California Davis, Sacramento, CA, USA, 2009. 927 kB.

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.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

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

Coppola, M; Mondola, R. Bromo-DragonFly: Chemistry, pharmacology and toxicology of a benzodifuran derivative producing LSD-like effects. J. Addict. Res. Ther., 1 Oct 2012, 3 (4), 133. 1.2 MB. http://dx.doi.org/10.4172/2155-6105.1000133

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. 1.7 MB. http://dx.doi.org/10.1371/journal.pone.0078515

Parker, MA; Marona-Lewicka, D; Lucaites, VL; Nelson, DL; Nichols, DE. A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J. Med. Chem., 1 Jan 1998, 41 (26), 5148–5149. 81 kB. http://dx.doi.org/10.1021/jm9803525

O’Connor, RE; Keating, JJ. Characterization of synthetic routes to ‘Bromo-DragonFLY’ and benzodifuranyl isopropylamine homologues utilizing ketone intermediates. Part 1: Synthesis of ketone precursors. Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 658-667. 812 kB. http://dx.doi.org/10.1002/dta.1504

Wood, DM; Looker, JJ; Shaikh, L; Lidder, S; Ramsey, J; Holt, DW; Dargan, PI. Delayed onset of seizures and toxicity associated with recreational use of Bromo-dragonFLY. J. Med. Toxicol., 1 Dec 2009, 5 (4), 226–229. 732 kB. http://dx.doi.org/10.1007/BF03178273

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. http://dx.doi.org/10.1007/s11419-009-0083-0

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. http://dx.doi.org/10.1016/j.bmc.2008.02.033

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3), 364–381. 817 kB. http://dx.doi.org/10.1016/j.neuropharm.2011.01.017

Chambers, JJ; Kurrasch-Orbaugh, DM; Parker, MA; Nichols, DE. Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT2A/2C receptor agonists. J. Med. Chem., 1 Jan 2001, 44 (6), 1003–1010. 337 kB. http://dx.doi.org/10.1021/jm000491y

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2.3 MB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

N-Methyl-DOB-dragonFLY
2C-B-DFLY · 2C-B-dragonFLY
720
TFM-DFLY · DOTFM-dragonFLY
DragonFLY
I-DFLY
DOM-DFLY
717
718
719
DOB-2-butterFLY-5-dragonFLY
BDBat
DOB-2-dragonFLY-5-butterFLY
BDE
BDE
BDBat
N-Methyl-DOB-dragonFLY
2C-B-DFLY · 2C-B-dragonFLY
720
TFM-DFLY · DOTFM-dragonFLY
DragonFLY
I-DFLY
DOM-DFLY
717
718
719
DOB-2-butterFLY-5-dragonFLY
BDBat
DOB-2-dragonFLY-5-butterFLY
BDE
BDE
BDBat
19 September 2017 · Creative Commons BY-NC-SA ·