α5IA

α₅IA (LS-193,268) is a nootropic drug invented in 2004 by a team working for Merck, Sharp and Dohme, which acts as a subtype-selective inverse agonist at the benzodiazepine binding site on the GABA_A receptor. It binds to the α₁, α₂, α₃ and α₅ subtypes.[1][2]

α₅IA

Clinical data
Other names	LS-193,268
ATC code	None
Identifiers
IUPAC name 3-(5-methylisoxazol-3-yl)-6-[(1-methyl-1H-1,2,3-triazol-4-yl)methoxy][1,2,4]triazolo[3,4-a]phthalazine
CAS Number	215874-86-5
PubChem CID	6918451
ChemSpider	5293648
UNII	1M7NI1A92L
CompTox Dashboard (EPA)	DTXSID10175950
Chemical and physical data
Formula	C17H14N8O2
Molar mass	362.353 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=NO1)C2=NN=C3N2N=C(C4=CC=CC=C43)OCC5=CN(N=N5)C
InChI InChI=1S/C17H14N8O2/c1-10-7-14(22-27-10)16-20-19-15-12-5-3-4-6-13(12)17(21-25(15)16)26-9-11-8-24(2)23-18-11/h3-8H,9H2,1-2H3 Key:NZMJFRXKGUCYNP-UHFFFAOYSA-N

See also

• GABA_A receptor negative allosteric modulator
• GABA_A receptor § Ligands

References

1. Sternfeld F, Carling RW, Jelley RA, Ladduwahetty T, Merchant KJ, Moore KW, et al. (April 2004). "Selective, orally active gamma-aminobutyric acidA alpha5 receptor inverse agonists as cognition enhancers". Journal of Medicinal Chemistry. 47 (9): 2176–9. doi:10.1021/jm031076j. PMID 15084116.
2. Street LJ, Sternfeld F, Jelley RA, Reeve AJ, Carling RW, Moore KW, et al. (July 2004). "Synthesis and biological evaluation of 3-heterocyclyl-7,8,9,10-tetrahydro-(7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazines and analogues as subtype-selective inverse agonists for the GABA(A)alpha5 benzodiazepine binding site". Journal of Medicinal Chemistry. 47 (14): 3642–57. doi:10.1021/jm0407613. PMID 15214791.