MRK-016

MRK-016
Names
	Preferred IUPAC name 3-tert-Butyl-7-(5-methyl-1,2-oxazol-3-yl)-2-[(1H-1,2,4-triazol-5-yl)methoxy]pyrazolo[1,5-d][1,2,4]triazine
Identifiers
CAS Number	342652-67-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	5293780;
PubChem CID	6918583;
UNII	TXZ4DVJ9MF ;
CompTox Dashboard (EPA)	DTXSID60426080;
	InChI InChI=1S/C17H20N8O2/c1-10-6-11(23-27-10)15-21-19-7-12-14(17(2,3)4)16(22-25(12)15)26-8-13-18-9-20-24(13)5/h6-7,9H,8H2,1-5H3 Key: QYSYOGCIDRANAR-UHFFFAOYSA-N;
	SMILES CN1N=CN=C1COC1=NN2C(C=NN=C2C2=NOC(C)=C2)=C1C(C)(C)C;
Properties
Chemical formula	C17H20N8O2
Molar mass	368.401 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

MRK-016 is a selective α₅ subunit-containing GABA_A negative allosteric modulator,^[1] that has nootropic properties. It has been found to produce rapid, ketamine-like antidepressant effects in animal models of depression.^[2]

References

^ Atack JR, Maubach KA, Wafford KA, O'Connor D, Rodrigues AD, Evans DC, et al. (November 2009). "In vitro and in vivo properties of 3-tert-butyl-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-1,2,4-triazol-5-ylmethoxy)-pyrazolo[1,5-d]-[1,2,4]triazine (MRK-016), a GABAA receptor alpha5 subtype-selective inverse agonist". The Journal of Pharmacology and Experimental Therapeutics. 331 (2): 470–84. doi:10.1124/jpet.109.157636. PMID 19704033. S2CID 688293.
^ Fischell J, Van Dyke AM, Kvarta MD, LeGates TA, Thompson SM (October 2015). "Rapid Antidepressant Action and Restoration of Excitatory Synaptic Strength After Chronic Stress by Negative Modulators of Alpha5-Containing GABAA Receptors". Neuropsychopharmacology. 40 (11): 2499–509. doi:10.1038/npp.2015.112. PMC 4569955. PMID 25900119.