L9787
L-655,708
≥98% (HPLC), powder
Synonym(s):
Ethyl (S)-11,12,13,13a-Tetrahydro-7-methoxy-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, L-655708
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About This Item
Empirical Formula (Hill Notation):
C18H19N3O4
CAS Number:
Molecular Weight:
341.36
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Quality Level
assay
≥98% (HPLC)
form
powder
solubility
DMSO: ≥6.0 mg/mL (Warmed), H2O: insoluble
originator
Merck & Co., Inc., Kenilworth, NJ, U.S.
SMILES string
CCOC(=O)c1ncn2-c3ccc(OC)cc3C(=O)N4CCCC4c12
InChI
1S/C18H19N3O4/c1-3-25-18(23)15-16-14-5-4-8-20(14)17(22)12-9-11(24-2)6-7-13(12)21(16)10-19-15/h6-7,9-10,14H,3-5,8H2,1-2H3/t14-/m0/s1
InChI key
YKYOQIXTECBVBB-AWEZNQCLSA-N
Gene Information
human ... GABRA5(2558)
Application
L-655,708 has been used as an α5 GABAA receptor inverse agonist to inhibit the discriminative stimulus of propofol in a dose-dependent manner.
Biochem/physiol Actions
Ligand for benzodiazepine site of GABAA receptors containing α5 subunits.
Novel ligand selective for the benzodiazepine site of GABAA receptors which contain the α5 subunit.
L-655,708 is an inverse agonist of the α5 γ-Aminobutyric acid type A (GABAA) receptor. It has an ability to increase cognition in rats.
Features and Benefits
This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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L-655,708 enhances cognition in rats but is not proconvulsant at a dose selective for alpha5-containing GABAA receptors
Atack JR, et al.
Neuropharmacology, 51(6), 1023-1029 (2006)
M Xue et al.
European journal of pain (London, England), 21(6), 1061-1071 (2017-02-02)
γ-Aminobutyric acid (GABA) type A receptors (GABA The C fibre-evoked field potentials were recorded in superficial dorsal horn of spinal cord, and the effects of α5-GABA Inhibition of α5-GABA α5-GABA Tonic inhibition generated by α5-GABA
C Sur et al.
Molecular pharmacology, 54(5), 928-933 (1998-11-06)
The gamma-aminobutyric acid (GABA)A receptor is a hetero-oligomer consisting of five subunits, the combination of which confers unique pharmacological properties to the receptor. To understand the physiological role of native GABAA receptors, it is critical to determine their subunit compositions.