L-689,560

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Cat.No. 0742 - L-689,560 | C17H15Cl2N3O3 | CAS No. 139051-78-8
Description: Very potent NMDA antagonist
Chemical Name: trans-2-Carboxy-5,7-dichloro-4-phenylaminocarbonylamino-1,2,3,4-tetrahydroquinoline
Purity: ≥99% (HPLC)
Datasheet
Citations (6)
Literature

Biological Activity

Very potent antagonist at the glycine-NMDA site. Also available as part of the NMDA Receptor - Glycine Site Tocriset™.

Licensing Information

Sold with the permission of Merck Sharp and Dohme Ltd.

Compound Libraries

L-689,560 is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 380.23
Formula C17H15Cl2N3O3
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 139051-78-8
PubChem ID 6604749
InChI Key UCKHICKHGAOGAP-UONOGXRCSA-N
Smiles ClC1=C2C(N[C@@H]([C@](O)=O)C[C@@H]2NC(NC3=CC=CC=C3)=O)=CC(Cl)=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 9.51 25
ethanol 38.02 100

Preparing Stock Solutions

The following data is based on the product molecular weight 380.23. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.63 mL 13.15 mL 26.3 mL
5 mM 0.53 mL 2.63 mL 5.26 mL
10 mM 0.26 mL 1.31 mL 2.63 mL
50 mM 0.05 mL 0.26 mL 0.53 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Leeson et al (1992) 4-Amido-2-carboxytetrahydroquinolines. Structure-activity relationship for antagonism at the glycine site of the NMDA receptor. J.Med.Chem. 35 1954 PMID: 1534584

Stone (2000) Development and therapeutic potential of kynurenic acid and kynurenine derivatives for neuroprotection. TiPS 21 149 PMID: 10740291

Leeson et al (1991) trans-2-Carboxy-4-substituted tetrahydroquinolines. Potent glycine-site NMDA receptor antagonists. Med.Chem.Res. 1 64 PMID:


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Keywords: L-689,560, supplier, potent, NMDA, antagonists, glycine, site, Glutamate, Receptors, N-Methyl-D-Aspartate, iGluR, Ionotropic, L689560, merck, NMDA, Receptors, NMDA, Receptors, Tocris Bioscience

6 Citations for L-689,560

Citations are publications that use Tocris products. Selected citations for L-689,560 include:

Potier et al (2010) Contribution of the d-Serine-Dependent Pathway to the Cellular Mechanisms Underlying Cognitive Aging. Front Aging Neurosci 2 1 PMID: 20552041

Dargan et al (2009) ACET is a highly potent and specific kainate receptor antagonist: characterisation and effects on hippocampal mossy fibre function. Neuropharmacology 56 121 PMID: 18789344

Park et al (2016) Calcium-Permeable AMPA Receptors Mediate the Induction of the Protein Kinase A-Dependent Component of Long-Term Potentiation in the Hippocampus. J Neurosci 36 622 PMID: 26758849

Dennis et al (2016) Activation of Muscarinic M1 Acetylcholine Receptors Induces Long-Term Potentiation in the Hippocampus. Mol Brain 26 414 PMID: 26472558

Fang et al (2015) Regulated internalization of NMDA receptors drives PKD1-mediated suppression of the activity of residual cell-surface NMDA receptors. Toxicol Lett 8 75 PMID: 26584860

Eales et al (2014) The MK2/3 cascade regulates AMPAR trafficking and cognitive flexibility. Nat Commun 5 4701 PMID: 25134715


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