Chemistry:EZS-8

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EZS-8, also known as 3-(2-aminoethyl)quinazoline-2,4-dione, is a very-low-potency serotonin 5-HT2A receptor partial agonist related to ketanserin.[1][2][3][4] It has about 0.15% of the potency (EC50 = 66,000 nM) and 46% of the efficacy (Emax) of serotonin as a serotonin 5-HT2A receptor agonist in vitro.[1][2][3][4] The N-(2-methoxy)benzyl analogue of EZS-8, RH-34, has 250-fold greater potency as a serotonin 5-HT2A receptor agonist in comparison.[2][3][4] EZS-8 was first described in the scientific literature by 1999.[1] N-Benzyl derivatives of EZS-8 like RH-34 had been described as early as 1996 or 1998.[5][6]

References

  1. ↑ 1.0 1.1 1.2 "Preparation and in vitro pharmacology of novel secondary amine-type 5-HT2A receptor agonists: from submillimolar to subnanomolar activity.". Arch. Pharm. Pharm. Med. Chem 332: 34. 1999. https://bitnest.netfirms.com/external/Arch.Pharm.Pharm.Med.Chem/331.S1.34. 
  2. ↑ 2.0 2.1 2.2 "Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function". Naunyn-Schmiedeberg's Archives of Pharmacology 365 (1 Suppl): R21–R40. 2002. doi:10.1007/s00210-002-0604-4. https://bitnest.netfirms.com/external/N-S.Arch.Pharmacol/365.S1.R29. 
  3. ↑ 3.0 3.1 3.2 Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD.). Universität Regensburg. Table 5.1: Agonistic potency (pEC50) and intrinsic activity (Emax) of 5-HT2AR partial agonistic arylethylamines (indole, methoxybenzene and quinazolinedione derivatives) used in the study. [...]
  4. ↑ 4.0 4.1 4.2 "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=57923f10abb4717589fdbe8dc2be132b0e9ac7aa. 
  5. ↑ "P 8.10. Congeners of 3-(2-benzylaminoethyl)-2, 4-quinazolinedione: Partial agonists for rat vascular 5-HT2A receptors.". Naunyn-Schmiedebergs Archives of Pharmacology 358 (1): R105. January 1998. https://bitnest.netfirms.com/external/N-S.Arch.Pharmacol/358.S1.R105. 
  6. ↑ "Abstracts: 331: Characterization of the Partial Agonism of Ergoline Reverse Esters, Indolyltetrahydropyridines, and Quinazolinediones at 5-HT2A receptors in Rat Tail Artery". Naunyn-Schmiedeberg's Archives of Pharmacology 353 (S4): R1–R166 (R90–R91). 1996. doi:10.1007/BF00625102. ISSN 0028-1298. http://link.springer.com/10.1007/BF00625102. "The aim of the study was to characterize the partial agonism of congeners of well-established 5-HT2A receptor ligands, identified in a series of ergot alkaloids (so-called ergoline reverse esters with lysergol and dihydrolysergol-I as alcoholic component), indolyltetrahydropyridines (RU 24969 and two derivatives), and quinazolinediones (derivatives of ketanserin), at 5-HT2A receptors in rat tail artery. [...] Quinazolinediones (derivatives of ketanserin) showed weak agonist activity (pKp = 3.83 - 4.66, α = 0.17 - 0,46) and antagonized contractile responses to 5-HT with calculated pKp values of 3.52 - 5.12.". 



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