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2C-EF-FLY; 2-[8-(2-Fluoroethyl)-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl]ethan-1-amine
2066
Variant: R4 all
Analogues: 5 5

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

Formula: C14H18FNO2 Molecular weight: 251.2966232 g/mol InChI Key: NUNWOBYVOQRPKC-UHFFFAOYSA-N

InChI=1S/C14H18FNO2/c15-5-1-9-11-3-7-18-14(11)10(2-6-16)12-4-8-17-13(9)12/h1-8,16H2

Five R4 analogues:
2020
Analogue 1: Removing 2-Fluoroethyl at R4

2C-FLY

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

Formula: C12H15NO2 Molecular weight: 205.253 g/mol InChI Key: TUZLDMANNCPSHX-UHFFFAOYSA-N

InChI=1S/C12H15NO2/c13-4-1-10-9-3-6-14-11(9)7-8-2-5-15-12(8)10/h7H,1-6,13H2

PubChem CID: 10798284; ChemSpider: 8973590

Shulgin Index: See #68 FLY; Table: 6 Page: 356 Row: 2

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. doi:10.1016/j.bmc.2008.02.033

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. doi:10.1021/jm960199j

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.

2021
Analogue 2: Substituting Bromo for 2-Fluoroethyl at R4

2C-B-FLY

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

Formula: C12H14BrNO2 Molecular weight: 284.14906 g/mol InChI Key: YZDFADGMVOSVIX-UHFFFAOYSA-N

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

PubChem CID: 10265873; ChemSpider: 8441352; Erowid: 2C-B-Fly; Wikipedia: 2C-B-FLY

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

Whiteside, MS. Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes. UW-LaCrosseJUR, 1999, 2, 61–68. 272 kB.

Prescher, JA. Design and synthesis of substituted furobenzopyrans as new serotonergic molecular probes. UW-LaCrosseJUR, 2001, 4, 143–152. 753 kB.

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. doi:10.1007/s11419-009-0083-0

Whiteside, MS; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Nichols, DE; Monte, A. Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes. Bioorg. Med. Chem., 1 Jan 2002, 10 (10), 3301–3306. 141 kB. doi:10.1016/S0968-0896(02)00209-2

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

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.

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. doi:10.1016/j.bmc.2008.02.033

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. doi:10.1021/jm960199j

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.

2027
Analogue 3: Substituting Methyl for 2-Fluoroethyl at R4

2C-D-FLY
2C-MeFLY

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

Formula: C13H17NO2 Molecular weight: 219.27958 g/mol InChI Key: JQNMKHHJXLRJQV-UHFFFAOYSA-N

InChI=1S/C13H17NO2/c1-8-9-3-6-16-13(9)10(2-5-14)11-4-7-15-12(8)11/h2-7,14H2,1H3

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

348
Analogue 4: Substituting Trifluoromethyl for 2-Fluoroethyl at R4

2C-TFM-FLY

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

Formula: C13H14F3NO2 Molecular weight: 273.2509696 g/mol InChI Key: LQEZYUCLMAYTNA-UHFFFAOYSA-N

InChI=1S/C13H14F3NO2/c14-13(15,16)10-9-3-6-18-11(9)7(1-4-17)8-2-5-19-12(8)10/h1-6,17H2

PubChem CID: 68108024

Chambers, JJ. Use of conformationally-restricted analogues and homology modeling to provide insight into the nature of the 5-HT2A receptor agonist binding site. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2002. 8389 kB.

7920
Analogue 5: Substituting Iodo for 2-Fluoroethyl at R4

2C-I-FLY

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

Formula: C12H14INO2 Molecular weight: 331.14953 g/mol InChI Key: SDULYHWSVCNNAO-UHFFFAOYSA-N

InChI=1S/C12H14INO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2

Shulgin Index: See #68 FLY; Table: 7 Page: 356 Row: 20

Show all five analogues and isomers Show only the five R4 analogues
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