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L9787

L-655,708

Name: L-655,708
Brand: SIGMA

≥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:

130477-52-0

Molecular Weight:

341.36

NACRES:

NA.77

PubChem Substance ID:

24278527

UNSPSC Code:

12352200

MDL number:

MFCD02684528

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Quality Level

100

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.

Ligand for benzodiazepine site of GABA_A receptors containing α₅ subunits.

Novel ligand selective for the benzodiazepine site of GABA_A 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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

Autoradiographic localization of alpha5 subunit-containing GABAA receptors in rat brain.

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

α5GABAA receptors play a pronociceptive role and avoid the rate-dependent depression of the Hoffmann reflex in diabetic neuropathic pain and reduce primary afferent excitability.

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 GABA_A receptors which contain the α₅ subunit.

Quirk, K., et al.

Neuropharmacology, 356, 1331-1335 (1996)

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)

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Global Trade Item Number

SKU	GTIN
L9787-25MG	04061832557045
L9787-5MG	04061832557052

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