SH-053-R-CH3-2′F

SH-053-R-CH3-2′F

Systematic (IUPAC) name
(R)-8-ethynyl-6-(2-fluorophenyl)-4-methyl-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester
Identifiers
CAS Number	872874-14-1
PubChem	CID 11574585
Chemical data
Formula	C23H18FN3O2
Molar mass	387.406 g/mol
SMILES Fc2ccccc2C1=NC(C)c3c(C(=O)OCC)ncn3-c(cc4)c1cc4C#C

SH-053-R-CH3-2′F is a drug used in scientific research which is a benzodiazepine derivative. It produces some of the same effects as other benzodiazepines, but is much more subtype-selective than most other drugs of this class, having high selectivity, binding affinity and efficacy at the α₅ subtype of the GABA_A receptor. This gives much tighter control of the effects produced, and so while SH-053-R-CH3-2′F retains sedative and anxiolytic effects, it does not cause ataxia at moderate doses.^[1] SH-053-R-CH3-2′F also blocks the nootropic effects of the α₅-selective inverse agonist PWZ-029, so amnesia is also a likely side effect.^[2]

See also

• QH-ii-066

References

1. Savić MM, Huang S, Furtmüller R, Clayton T, Huck S, Obradović DI, Ugresić ND, Sieghart W, Bokonjić DR, Cook JM. Are GABAA receptors containing alpha5 subunits contributing to the sedative properties of benzodiazepine site agonists? Neuropsychopharmacology. 2008 Jan;33(2):332-9. PMID 17392731
2. Savić MM, Clayton T, Furtmüller R, Gavrilović I, Samardzić J, Savić S, Huck S, Sieghart W, Cook JM. PWZ-029, a compound with moderate inverse agonist functional selectivity at GABA(A) receptors containing alpha5 subunits, improves passive, but not active, avoidance learning in rats. Brain Research. 2008 May 7;1208:150-9. doi:10.1016/j.brainres.2008.02.020 PMID 18394590