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Names

DOB-5-hemiFLY
B-SF
5-MeO-7-Br-4-APDB

IUPAC name

1-(7-Bromo-5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2-amine

ID 354 · Formula C₁₂H₁₆BrNO₂ · Molecular weight 286.165

InChI InChI=1S/C12H16BrNO2/c1-7(14)5-9-8-3-4-16-12(8)10(13)6-11(9)15-2/h6-7H,3-5,14H2,1-2H3

InChI Key PKJQSBXFDIUPBW-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES COc1cc(Br)c2c(c1CC(N)C)CCO2

ChemSpider 9066709
PubChem 10891445
Wikipedia, see Substituted benzofuran

Shulgin Index #17 B-SF · Table 6Page 355Row 25

Phenethylamine: Von der Strucktur zur Funktion DOB-5-hemiFLY: 7.3 (16) 496, 497 · B-SF: 8.5 (383) 851, 852, 860

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. https://doi.org/10.1021/jm00105a043 #6b MS,NMR

Waldman, SR; Monte, AP; Bracey, A; Nichols, DE. One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of Ortho-methoxylated phenylisopropylamines. Tetrahedron Lett., 1 Jan 1996, 37 (44), 7880–7892. 246 kB. https://doi.org/10.1016/0040-4039(96)01807-2 #1a

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 #50

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 #48

Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1 Jan 1994; pp 3–41. 8.1 MB. #33

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 #4

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nelson, DL; Nichols, DE. Conformationally restricted tetrahydro-1-benzoxepin analogs of hallucinogenic phenethylamines. Med. Chem. Res., 1 Sep 1995, 5 (9), 651–663. 2.0 MB. #4 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 #36

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. #247 In German. MS,NMR,IR

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT_2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. https://doi.org/10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B #pn25

2CB-Ind

DOB-2-hemiFLY

5755

2-Amino-6-bromo-5,8-dimethoxytetralin · DOB-AT

BBOX-5-MA

2C-B-PYR

7 Dec 2019 · · Isomer Design