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Names

B-PLY
DOB-butterFLY

IUPAC names

1-(10-Bromo-2,3,4,7,8,9-hexahydrobenzo[1,2-b:4,5-b′]dipyran-5-yl)propan-2-amine
1-(10-Bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g]chromen-5-yl)propan-2-amine

ID 2036 · Formula C₁₅H₂₀BrNO₂ · Molecular weight 326.229

InChI InChI=1S/C15H20BrNO2/c1-9(17)8-12-10-4-2-7-19-15(10)13(16)11-5-3-6-18-14(11)12/h9H,2-8,17H2,1H3

InChI Key PDCVVUDZIAVPTI-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CC(Cc1c2OCCCc2c(c2c1CCCO2)Br)N

ChemSpider 8511936
PubChem 10336477

Shulgin Index See #68 FLY · Table 7Page 356Row 31

Phenethylamine: Von der Strucktur zur Funktion DOB-butterFLY: 8.5 (394) 856, 857, 860

Schultz, DM; Prescher, JA; Kidd, S; Marona-Lewicka, D; Nichols, DE; Monte, A. ‘Hybrid’ benzofuran–benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. Bioorg. Med. Chem., 1 Jan 2008, 16 (11), 6242–6251. 228 kB. https://doi.org/10.1016/j.bmc.2008.04.030

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 #41

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

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.

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.

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

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

4-Br-EPH · 4-Bromoethylphenidate

Bromo-methoxetamine

7 Dec 2019 · · Isomer Design