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Name

2C-B-FLY

IUPAC name

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

ID 2021 · Formula C₁₂H₁₄BrNO₂ · Molecular weight 284.149

InChI InChI=1S/C12H14BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2

InChI Key YZDFADGMVOSVIX-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES NCCc1c2OCCc2c(c2c1CCO2)Br

ChemSpider 8441352
PubChem 10265873
Wikidata Q4633042
Erowid 2C-B-Fly
Wikipedia 2C-B-FLY
Wikipedia, see also Substituted benzofuran
Blotter 2C-B-FLY
Blotter 2C-B-FLY
PsychonautWiki 2C-B-FLY
Project Response 2C-B-fly (1647-16)
bluelight.org The Big & Dandy 2C-B-Fly Thread
bluelight.org 2C-B-FLY Effects and Ratings Survey Results

Shulgin Index See #68 FLY · Table 7Page 356Row 18

Phenethylamine: Von der Strucktur zur Funktion 2C-B-FLY: 8.5 (388) 853, 854, 865

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 #7d

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 #8

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. #250 In German. MS,NMR,IR

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. https://doi.org/10.1371/journal.pone.0009019

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

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

Prescher, JA. Design and synthesis of substituted furobenzopyrans as new serotonergic molecular probes. UW-LaCrosseJUR, , 4, 143–152. 753 kB.

Whiteside, MS. Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT_2A/2C receptor probes. UW-LaCrosseJUR, , 2, 61–68. 272 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. #2C-B-FLY GC,MS,NMR,IR

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

Ray, TS. Constructing the ecstasy of MDMA from its component mental organs: Proposing the primer/probe method. Med. Hypotheses, 1 Feb 2016, 87 48–60. 455 kB. https://doi.org/10.1016/j.mehy.2015.12.018

McGonigal, MK; Wilhide, JA; Smith, PB; Elliott, NM; Dorman, FL. Analysis of synthetic phenethylamine street drugs using direct sample analysis coupled to accurate mass time of flight mass spectrometry. Forensic Sci. Int., 1 Jun 2017, 275 83–89. 2.3 MB. https://doi.org/10.1016/j.forsciint.2017.02.025 #2C-B FLY

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

King, LA. New phenethylamines in Europe. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

EMCDDA. New drugs in Europe, 2007, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2008. 381 kB. #1

Wagmann, L; Brandt, SD; Stratford, A; Maurer, HH; Meyer, MR. Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases. Drug Test. Anal., 6 Sep 2018, 11 (2), 318-324. 650 kB. https://doi.org/10.1002/dta.2494 #2C-B-FLY

Chapman, SJ. Novel Psychoactive Spectra: NMR of (mostly) Novel Psychoactive Substances. BLOTTER, 25 Jun 2018, 3 (2). https://doi.org/10.16889/isomerdesign-6 #2C-B-FLY NMR

Wagmann, L; Hempel, N; Richter, LHJ; Brandt, SD; Stratford, A; Meyer, MR. Phenethylamine‐derived new psychoactive substances 2C‐E‐FLY, 2C‐EF‐FLY, and 2C‐T‐7‐FLY: Investigations on their metabolic fate including isoenzyme activities and their toxicological detectability in urine screenings. Drug Test. Anal., 12 Jul 2019, 11 (10), 1507-1521. 731 kB. https://doi.org/10.1002/dta.2675 #2C-B-FLY

Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S2 Benzodifurans 2C-B-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. #12 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 #2C-B-FLY

Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #2C-B-Fly

Pottie, E; Cannaert, A; Stove, CP. In vitro structure–activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor. Arch. Toxicol., 5 Jul 2020, n/a. 919 kB. https://doi.org/10.1007/s00204-020-02836-w #2C-B-FLY

Flanagan, TW; Billac, GB; Landry, AN; Sebastian, MN; Cormier, SA; Nichols, CD. Structure–activity relationship analysis of psychedelics in a rat model of asthma reveals the anti-inflammatory pharmacophore. ACS Pharmacol. Transl. Sci., 13 Aug 2020, n/a. 13.3 MB. https://doi.org/10.1021/acsptsci.0c00063 #2C-B-Fly

DOB-5-hemidragonFLY

DOB-2-hemidragonFLY

2C-B-5-hemiFLY-α6 · BNAP

5754

7 Dec 2019 · · Isomer Design