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Merck
CN

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:
130477-52-0
Molecular Weight:
341.36
MDL number:
MFCD02684528
UNSPSC Code:
12352200
PubChem Substance ID:
24278527
NACRES:
NA.77

Key Documents

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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 GABAA receptors containing α5 subunits.
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

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Certificates of Analysis (COA)

Lot/Batch Number
0000185795
0000185796
0000185795
0000185796
0000129552

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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)
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)
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
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