13-Fluorolysergol

vanc 6 13-Fluorolysergol.svg skin-invert-image 150px Selective serotonin 5-HT2A receptor weak partial agonist or antagonist 132505474 (13-Fluoro-6-methyl-9,10-didehydroergolin-8β-yl)methanol [(6aR,9R)-2-fluoro-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol 16 17 1 2 1 CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC(=CC2=C34)F)CO 1S/C16H17FN2O/c1-19-7-9(8-20)2-12-13-4-11(17)5-14-16(13)10(6-18-14)3-15(12)19/h2,4-6,9,15,18,20H,3,7-8H2,1H3/t9-,15-/m1/s1 UBKCOUCTZVGLJQ-RFAUZJTJSA-N 13-Fluorolysergol, specifically as the (+)-enantiomer (+)-13-fluorolysergol, is a selective serotonin 5-HT2A receptor weak partial agonist or antagonist of the ergoline family. Duan W, Cao D, Wang S, Cheng J Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants Chemical Reviews 124 1 124–163 January 2024 38033123 10.1021/acs.chemrev.3c00375 The natural alkaloid (+)-lysergol (72) and its synthetic analogues were also reported to display 5-HT2AR activity as agonists, evaluated in a calcium flux assay using CHO-K1 cells.166 For example, (+)-lysergol was demonstrated to be a partial agonist at the 5-HT2AR (EC50 = 1.6 nM, Emax = 51% (5- HT 100%)), but it was also a potent agonist of the 5-HT2CR (EC50 = 6.6 nM).166 (+)-13-Fluorolysergol (73) exhibited weaker partial agonist activity (EC50 = 12 nM, Emax = 17% (5- HT 100%)). However, unexpectedly, this compound was reported to lose the ability to activate the 5-HT2B and 5-HT2C receptors.166 Lysergine (74) also demonstrated comparable potency at the 5-HT2AR (EC50 = 2.7 nM), with 54- and 38-fold selectivity against the 5-HT2BR (EC50 = 145 nM) and 5- HT2CR (EC50 = 103 nM), respectively.166 Yuan H, Guo Z, Luo T Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity Organic Letters 19 3 624–627 February 2017 28106398 10.1021/acs.orglett.6b03779 It is highly selective for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2B and 5-HT2C receptors (EC50 half-maximal effective concentration = >10,000nM). (+)-13-Fluorolysergol has relatively weak maximal efficacy in activating the serotonin 5-HT2A receptor (Emax maximal efficacy = 17%). It is a derivative of lysergol. See also Lysergine References External links 13-Fluorolysergol Category:Ergolines Category:Fluoroarenes Category:Selective 5-HT2A receptor agonists