SX-3228

SX-3228

Systematic (IUPAC) name
(3E)-6-benzyl-3-(5-methoxy-1,3,4-oxadiazol-2(3H)-ylidene)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(3H)-one
Identifiers
CAS Number	156364-04-4
PubChem	CID 5487538
ChemSpider	14241619
Synonyms	5,6,7,8-tetrahydro-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-6-(phenylmethyl)-1,6-naphthyridin-2(1H)-one
Chemical data
Formula	C18H18N4O3
Molar mass	338.361 g/mol
SMILES COc1nnc(o1)C/3=C/C=4CN(Cc2ccccc2)CCC=4NC\3=O
InChI InChI=1S/C18H18N4O3/c1-24-18-21-20-17(25-18)14-9-13-11-22(8-7-15(13)19-16(14)23)10-12-5-3-2-4-6-12/h2-6,9H,7-8,10-11H2,1H3,(H,19,23) Key:BZLLVTYOOJNQIF-UHFFFAOYSA-N
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SX-3228 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.

SX-3228 is a subtype-selective GABA_A positive allosteric modulator acting primarily at the α1 subtype. It thus has similar effects to other α1-selective drugs such as zolpidem and zaleplon in animal studies.^[1][2] It only partly substitutes for ethanol, and is a strong sedative-hypnotic with only limited anxiolytic effects which appear only at doses that also produce significant sedation.^[3][4]

References

1. Sanger DJ. The effects of new hypnotic drugs in rats trained to discriminate ethanol. Behavioural Pharmacology. 1997 Aug;8(4):287-92.
2. Griebel G, Perrault G, Tan S, Schoemaker H, Sanger DJ. Comparison of the pharmacological properties of classical and novel BZ-omega receptor ligands. Behavioural Pharmacology. 1999 Sep;10(5):483-95.
3. Griebel G, Perrault G, Sanger DJ. Limited anxiolytic-like effects of non-benzodiazepine hypnotics in rodents. Journal of Psychopharmacology. 1998;12(4):356-65.
4. Alvariño F, Monti JM, Jantos H, Monti D. Effect of SX-3228, a selective ligand for the BZ1 receptor, on sleep and waking during the light-dark cycle in the rat. Brazilian Journal of Medical and Biological Research. 1999 Aug;32(8):1007-14.