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Submit ReviewSYM 2081
Description: Highly selective kainate agonist
Chemical Name: (2S,4R)-4-Methylglutamic acid
Purity: ≥97% (HPLC)
Biological Activity
Potent and highly selective kainate receptor agonist, with an IC50 for inhibition of [3H]-kainate binding of 35 nM and almost 3,000- and 200-fold selectivity for kainate receptors over AMPA and NMDA receptors respectively. Also selectively inhibits the cloned excitatory amino acid transporter EAAT2 at higher concentrations.
Licensing Information
Sold with the permission of Annovis Inc.
Technical Data
| M. Wt | 161.16 |
| Formula | C6H11NO4 |
| Storage | Store at RT |
| Purity | ≥97% (HPLC) |
| CAS Number | 31137-74-3 |
| PubChem ID | 95883 |
| InChI Key | KRKRAOXTGDJWNI-DMTCNVIQSA-N |
| Smiles | [H][C@@](N)(C(O)=O)C[C@]([H])([C@](O)=O)C |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 8.06 | 50 |
Preparing Stock Solutions
The following data is based on the product molecular weight 161.16. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.5 mM | 12.41 mL | 62.05 mL | 124.1 mL |
| 2.5 mM | 2.48 mL | 12.41 mL | 24.82 mL |
| 5 mM | 1.24 mL | 6.21 mL | 12.41 mL |
| 25 mM | 0.25 mL | 1.24 mL | 2.48 mL |
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References
References are publications that support the biological activity of the product.
Donevan et al (1998) The methylglutamate, SYM 2081, is a potent and highly selective agonist at kainate receptors. J.Pharmacol.Exp.Ther. 285 539 PMID: 9580595
Jones et al (1997) Desensitization of kainate receptors by kainate, glutamate and diastereomers of 4-methylglutamate. Neuropharmacology 36 853 PMID: 9225313
Savidge et al (1999) Characterisation of kainate receptor mediated whole-cell currents in rat cultured cerebellar granule cells. Neuropharmacology 38 375 PMID: 10219975
Zhou et al (1997) (2S,4R)-4-Methylglutamic acid (SYM 2081): a selective, high affinity ligand for kainate receptors. J.Pharmacol.Exp.Ther. 280 422 PMID: 8996224
If you know of a relevant reference for SYM 2081, please let us know.
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Keywords: SYM 2081, SYM 2081 supplier, inhibitors, inhibits, EAAT2, kainate, receptors, agonist, selective, EAAT, Excitatory, Amino, Acid, Transporters, GLT-1, Glutamate, Monoamine, Neurotransmitter, iGluR, Ionotropic, SYM2081, Kainate, Receptors, 0903, Tocris Bioscience
6 Citations for SYM 2081
Citations are publications that use Tocris products. Selected citations for SYM 2081 include:
Pollok and Reiner (2020) Subunit-selective iGluR antagonists can potentiate heteromeric receptor responses by blocking desensitization Proc Natl Acad Sci USA 117 25851 PMID: 32999066
Vielma et al (2014) Nitric oxide modulates the temporal properties of the glutamate response in type 4 OFF bipolar cells. PLoS One 9 e114330 PMID: 25463389
Rojas et al (2013) Activation of group I metabotropic glutamate receptors potentiates heteromeric kainate receptors. Mol Pharmacol 83 106 PMID: 23066089
Gangadharan et al (2011) Peripheral calcium-permeable AMPA receptors regulate chronic inflammatory pain in mice. J Clin Invest 121 1608 PMID: 21383497
Santos et al (2009) Transmission efficacy and plasticity in glutamatergic synapses formed by excitatory interneurons of the substantia gelatinosa in the rat spinal cord. PLoS One 4 e8047 PMID: 19956641
Yoshii et al (2013) A Myosin Va mutant mouse with disruptions in glutamate synaptic development and mature plasticity in visual cortex. Addict Biol 33 8472 PMID: 23658184
Do you know of a great paper that uses SYM 2081 from Tocris? Please let us know.
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