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Merck

L9787

Sigma-Aldrich

L-655,708

≥98% (HPLC), powder

Sinónimos:

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

Fórmula empírica (notación de Hill):
C18H19N3O4
Número de CAS:
Peso molecular:
341.36
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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

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.
Novel ligand selective for the benzodiazepine site of GABAA receptors which contain the α5 subunit.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Visite la Librería de documentos

Contribution of the alpha5 GABAA receptor to the discriminative stimulus effects of propofol in rat
Wang B, et al.
Neuroreport, 29(5), 347-347 (2018)
C Sur et al.
Brain research, 822(1-2), 265-270 (1999-03-20)
Multiple subtypes of GABAA receptors are expressed in the rat central nervous system (CNS). To determine the distribution and proportion of alpha5 subunit containing receptors, quantitative autoradiographic analyses were performed with both [3H]L-655,708 and [3H]Ro15-1788, an alpha5 selective and a
José E Hernández-Reyes et al.
Pain, 160(6), 1448-1458 (2019-05-21)
Diabetic neuropathy is an incapacitating complication in diabetic patients. The cellular and molecular mechanisms involved in this pathology are poorly understood. Previous studies have suggested that the loss of spinal GABAergic inhibition participate in painful diabetic neuropathy. However, the role
[3H]L-655,708, a novel ligand selective for the benzodiazepine site of GABAA receptors which contain the α5 subunit.
Quirk, K., et al.
Neuropharmacology, 356, 1331-1335 (1996)
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.

Artículos

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

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