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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
NACRES:
NA.77
PubChem Substance ID:
24278527
UNSPSC Code:
12352200
MDL number:
MFCD02684528

Key Documents

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Product Name

L-655,708, ≥98% (HPLC), powder

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

SMILES string

CCOC(=O)c1ncn2-c3ccc(OC)cc3C(=O)N4CCCC4c12

InChI key

YKYOQIXTECBVBB-AWEZNQCLSA-N

assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥6.0 mg/mL (Warmed)
H2O: insoluble

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

Quality Level

100

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000185795
0000185796
0000185795
0000185796
0000129552

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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.
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)
Flavia R Carreno et al.
The international journal of neuropsychopharmacology, 20(6), 504-509 (2017-03-25)
Selective augmentation of hippocampal activity in ways similar to that caused by ketamine may have therapeutic advantages over ketamine, which has psychotomimetic and reinforcing effects likely due to effects outside the hippocampus (i.e., off-target effects). Here we evaluated the antidepressant-like
[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)
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