U-90042

U-90042

Identifiers
IUPAC name 11-Chloro-5-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-2,3-dihydrodiimidazo[1,2-c:1',5'-a]quinazoline
CAS Number	134516-99-7
PubChem (CID)	9928470
ChemSpider	8104103
Chemical and physical data
Formula	C17H13ClN6O
Molar mass	352.78 g/mol
3D model (Jmol)	Interactive image
SMILES ClC1=CC2=C(C=C1)N3C=NC(C4=NOC(C5CC5)=N4)=C3N6C2=NCC6
InChI InChI=1S/C17H13ClN6O/c18-10-3-4-12-11(7-10)15-19-5-6-23(15)17-13(20-8-24(12)17)14-21-16(25-22-14)9-1-2-9/h3-4,7-9H,1-2,5-6H2 Key:CLPSAAPUJUVQPP-UHFFFAOYSA-N
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U-90042 is a sedative and hypnotic drug used in scientific research. It has similar effects to sedative-hypnotic benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine hypnotic.

U-90042 is a GABA_A agonist acting primarily at the α1, α3 and α6 subtypes, with a Ki of 7.8nM at α1, 9.5nM at α3 and 11.0nM at α6. It produces sedation and ataxia and prolongs sleeping time in mice, rats and monkeys, but does not produce amnesia and blocks the amnestic effect of diazepam, reflecting its different subtype affinity compared to benzodiazepine drugs.^[1] It was developed by a team at Novo Nordisk in the 1980s.^[2]

References

1. Tang, AH; Smith, MW; Carter, DB; Im, WB; Vonvoigtlander, PF (1995). "U-90042, a sedative/hypnotic compound that interacts differentially with the GABAA receptor subtypes". The Journal of Pharmacology and Experimental Therapeutics. 275 (2): 761–7. PMID 7473164.
2. US Patent 5100895 Heterocyclic compounds and their preparation and use