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Names

DOH-FLY
FLY
1-(2,3,6,7-Tetrahydrofuro[2,3-f][1]benzofuran-4-yl)propan-2-amine

IUPAC name

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

ID 2022 · Formula C₁₃H₁₇NO₂ · Molecular weight 219.28

InChI InChI=1S/C13H17NO2/c1-8(14)6-11-10-3-5-15-12(10)7-9-2-4-16-13(9)11/h7-8H,2-6,14H2,1H3

InChI Key QTMQYHDNFFQCRI-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CC(Cc1c2OCCc2cc2c1CCO2)N

ChemSpider 8784278
PubChem 10608911

Shulgin Index #68 FLY · Table 6Page 356Row 3

Phenethylamine: Von der Strucktur zur Funktion FLY: 7.3 (19) 497, 498, 515 · 9.3 (2) 928, 929 · H-FLY: 7.3 (19) 499

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 #7a

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 #18

Chambers, JJ; Kurrasch-Orbaugh, DM; Parker, MA; Nichols, DE. Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT_2A/2C receptor agonists. J. Med. Chem., 1 Mar 2001, 44 (6), 1003–1010. 337 kB. https://doi.org/10.1021/jm000491y #5a NMR

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. #261 In German. MS,NMR,IR

Parker, MA; Marona-Lewicka, D; Lucaites, VL; Nelson, DL; Nichols, DE. A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT_2A receptor. J. Med. Chem., 1 Dec 1998, 41 (26), 5148–5149. 382 kB. https://doi.org/10.1021/jm9803525 #4 NMR

Baralla, E; Nieddu, M; Burrai, L; Varoni, MV; Demontis, MP; Boatto, G. LC-MS/MS analysis of two new designer drugs (FLY series) in rat plasma and its application to a pharmacokinetic study. Leg. Med., 1 May 2019, 38 (2019), 58–63. 778 kB. https://doi.org/10.1016/j.legalmed.2019.04.004 #FLY LC,MS,NMR

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. #8 MS,NMR

N-Allyl-3,4-methylenedioxyamphetamine · N-Allyl-MDA · MDAL

2C-D-FLY · 2C-MeFLY

4-Ethynyl-2,5-dimethoxyamphetamine · DOYN

5,8-Dimethoxy-6-methyl-2-amino-3,4-didehydrotetralin · DOMAD

5-MeO-BFE · 5-MeO-DMBF · Dimemebfe

N-Cyclopropyl-3,4-methylenedioxyamphetamine · MDCP

2C-H-5-hemiFLY-β6

2,5-Dimethoxy-4-propynylphenethylamine · 2C-PYN

1337

2C-FLEA

2C-GNAT

2768

ATK-0101 · UWA-101 · α-Cyclopropyl-N-methyl-3,4-methylenedioxyphenethylamine · α-cPr-N-Me-3,4-MDPEA

10232

4-Ethynyl-2,6-dimethoxyamphetamine · ψ-DOYN

2,5-Dimethoxy-4-propargylphenethylamine · 2C-YNP

5-MeO-NEBF

Pethidinic acid

N-Acetyl-N,4-dimethylcathinone · N-Acetylmephedrone

3,4-MD-PCA

MDA-NPI

9644

Ritalinic acid

3-HO-DCK · HXM

4-MeO-BzPip

MPY

N-Desethyl MXE · N-Desethyl methoxetamine

14533

7 Dec 2019 · · Isomer Design