Skip to Content
Merck
All Photos(1)

Documents

Safety Information

L9787

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H19N3O4
CAS Number:
130477-52-0
Molecular Weight:
341.36
MDL number:
MFCD02684528
UNSPSC Code:
12352200
PubChem Substance ID:
24278527
NACRES:
NA.77

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

L9787-5MG:
L9787-VAR:
L9787-BULK:
L9787-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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.
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.
View All Related Papers

Articles

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service