Chemistry:13-Fluorolysergol

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13-Fluorolysergol, specifically as the (+)-enantiomer (+)-13-fluorolysergol, is a selective serotonin 5-HT2A receptor weak partial agonist or antagonist of the ergoline family.[1][2] It is highly selective for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2B and 5-HT2C receptors (EC50 = >10,000 nM).[1][2] (+)-13-Fluorolysergol has relatively weak maximal efficacy in activating the serotonin 5-HT2A receptor (Emax = 17%).[1][2] It is a derivative of lysergol.[1][2]

See also

  • Lysergine

References

  1. ↑ 1.0 1.1 1.2 1.3 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. 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. ↑ 2.0 2.1 2.2 2.3 "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Organic Letters 19 (3): 624–627. February 2017. doi:10.1021/acs.orglett.6b03779. PMID 28106398. 



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