13-Fluorolysergol

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13-Fluorolysergol
13-Fluorolysergol.svg
Clinical data
Other names(13-Fluoro-6-methyl-9,10-didehydroergolin-8β-yl)methanol
Drug class Selective serotonin 5-HT2A receptor weak partial agonist or antagonist
Identifiers
  • [(6aR,9R)-2-fluoro-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol
PubChem CID
Chemical and physical data
Formula C16H17FN2O
Molar mass 272.323 g·mol−1
3D model (JSmol)
  • CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC(=CC2=C34)F)CO
  • InChI=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
  • Key: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 and lysergic acid families. [1] [2] It is highly selective for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2B and 5-HT2C receptors (EC50 Tooltip half-maximal effective concentration = >10,000 nM). [1] [2] (+)-13-Fluorolysergol has relatively weak maximal efficacy in activating the serotonin 5-HT2A receptor (Emax Tooltip maximal efficacy = 17%). [1] [2] It is a derivative of lysergol. [1] [2]

Contents

See also

References

  1. 1 2 3 4 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID   38033123. 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
  2. 1 2 3 4 Yuan H, Guo Z, Luo T (February 2017). "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Organic Letters. 19 (3): 624–627. doi:10.1021/acs.orglett.6b03779. PMID   28106398.
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