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EZS-8

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EZS-8
Clinical data
Other names3-(2-Aminoethyl)quinazoline-2,4-dione
Drug classSerotonin 5-HT2A receptor partial agonist
ATC code
  • None
Identifiers
  • 3-(2-aminoethyl)-1H-quinazoline-2,4-dione
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC10H11N3O2
Molar mass205.217 g·mol−1
3D model (JSmol)
  • C1=CC=C2C(=C1)C(=O)N(C(=O)N2)CCN
  • InChI=1S/C10H11N3O2/c11-5-6-13-9(14)7-3-1-2-4-8(7)12-10(13)15/h1-4H,5-6,11H2,(H,12,15)
  • Key:NTAUXYQQSCPGHT-UHFFFAOYSA-N

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 (EC50Tooltip half-maximal effective concentration = 66,000 nM) and 46% of the efficacy (EmaxTooltip maximal efficacy) 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

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  1. ^ a b c Heim R, Pertz HH, Elz S (1999). "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.
  2. ^ a b c Elz S, Klass T, Heim R, Warnke U, Pertz HH (2002). "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. doi:10.1007/s00210-002-0604-4.
  3. ^ a b c 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. ^ a b c Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  5. ^ Heim R, Pertz H, Walther I, Elz S (January 1998). "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.
  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. 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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