SYM2081 | CAS#31137-74-3 |Kainate Receptor Agonist

MedKoo Cat#: 532799 | Name: SYM2081

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SYM2081 is a 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. SYM2081 also selectively inhibits the cloned excitatory amino acid transporter EAAT2 at higher concentrations.

Chemical Structure

SYM2081

CAS#31137-74-3

Theoretical Analysis

MedKoo Cat#: 532799

Name: SYM2081

CAS#: 31137-74-3

Chemical Formula: C6H11NO4

Exact Mass: 161.0688

Molecular Weight: 161.16

Elemental Analysis: C, 44.72; H, 6.88; N, 8.69; O, 39.71

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

SYM2081; SYM-2081; SYM 2081; (2S,4R)-Me-Glu.

IUPAC/Chemical Name

(2S,4R)-4-Methylglutamic acid

InChi Key

KRKRAOXTGDJWNI-DMTCNVIQSA-N

InChi Code

InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m1/s1

SMILES Code

N[C@@H](C[C@@H](C)C(O)=O)C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SYM2081 is a selective agonist of kainate receptors. It inhibits [3H]-kainate binding with an IC50 of 35 nM, almost 3000- and 200-fold selectivity for kainate receptors over AMPA and NMDA receptors respectively.

In vitro activity:

This study investigated several GluR5 ligands in acute and hyperalgesic states. In hemisected spinal cords in vitro, SYM2081 was inactive. Reference: Neuropharmacology. 2002 Sep;43(3):327-39. https://pubmed.ncbi.nlm.nih.gov/12243762/

In vivo activity:

The responses of mouse gastro-oesophageal vagal afferents to graded mechanical stimuli were investigated before and during application of selective GluR ligands to their peripheral endings. SYM-2081 had minor effects on mechanosensitivity, and the antagonist UBP 302 was ineffective. Reference: J Physiol. 2006 Nov 15;577(Pt 1):295-306. https://pubmed.ncbi.nlm.nih.gov/16945965/

	Solvent	mg/mL	mM
Solubility
	Water	50.0	310.25

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Mascias P, Scheede M, Bloms-Funke P, Chizh B. Modulation of spinal nociception by GluR5 kainate receptor ligands in acute and hyperalgesic states and the role of gabaergic mechanisms. Neuropharmacology. 2002 Sep;43(3):327-39. doi: 10.1016/s0028-3908(02)00112-0. PMID: 12243762. 2. Slattery JA, Page AJ, Dorian CL, Brierley SM, Blackshaw LA. Potentiation of mouse vagal afferent mechanosensitivity by ionotropic and metabotropic glutamate receptors. J Physiol. 2006 Nov 15;577(Pt 1):295-306. doi: 10.1113/jphysiol.2006.117762. Epub 2006 Aug 31. PMID: 16945965; PMCID: PMC2000674. 3. Stoffel W, Körner R, Wachtmann D, Keller BU. Functional analysis of glutamate transporters in excitatory synaptic transmission of GLAST1 and GLAST1/EAAC1 deficient mice. Brain Res Mol Brain Res. 2004 Sep 28;128(2):170-81. doi: 10.1016/j.molbrainres.2004.06.026. PMID: 15363892.

In vitro protocol:

In vivo protocol:

1. Slattery JA, Page AJ, Dorian CL, Brierley SM, Blackshaw LA. Potentiation of mouse vagal afferent mechanosensitivity by ionotropic and metabotropic glutamate receptors. J Physiol. 2006 Nov 15;577(Pt 1):295-306. doi: 10.1113/jphysiol.2006.117762. Epub 2006 Aug 31. PMID: 16945965; PMCID: PMC2000674. 2. Stoffel W, Körner R, Wachtmann D, Keller BU. Functional analysis of glutamate transporters in excitatory synaptic transmission of GLAST1 and GLAST1/EAAC1 deficient mice. Brain Res Mol Brain Res. 2004 Sep 28;128(2):170-81. doi: 10.1016/j.molbrainres.2004.06.026. PMID: 15363892.

1: Møllerud S, Kastrup JS, Pickering DS. A pharmacological profile of the high-affinity GluK5 kainate receptor. Eur J Pharmacol. 2016 Oct 5;788:315-20. doi: 10.1016/j.ejphar.2016.06.049. Epub 2016 Jun 29. PubMed PMID: 27373850. 2: Rasmussen JL, Storgaard M, Pickering DS, Bunch L. Rational design, synthesis and pharmacological evaluation of the (2R)- and (2S)-stereoisomers of 3-(2-carboxypyrrolidinyl)-2-methyl acetic acid as ligands for the ionotropic glutamate receptors. ChemMedChem. 2011 Mar 7;6(3):498-504. doi: 10.1002/cmdc.201000543. Epub 2011 Jan 25. PubMed PMID: 21268287. 3: Erreger K, Geballe MT, Kristensen A, Chen PE, Hansen KB, Lee CJ, Yuan H, Le P, Lyuboslavsky PN, Micale N, Jørgensen L, Clausen RP, Wyllie DJ, Snyder JP, Traynelis SF. Subunit-specific agonist activity at NR2A-, NR2B-, NR2C-, and NR2D-containing N-methyl-D-aspartate glutamate receptors. Mol Pharmacol. 2007 Oct;72(4):907-20. Epub 2007 Jul 10. PubMed PMID: 17622578. 4: Lalo U, Verkhratsky A, Pankratov Y. Ivermectin potentiates ATP-induced ion currents in cortical neurones: evidence for functional expression of P2X4 receptors? Neurosci Lett. 2007 Jun 27;421(2):158-62. Epub 2007 May 31. PubMed PMID: 17566648. 5: Stoffel W, Körner R, Wachtmann D, Keller BU. Functional analysis of glutamate transporters in excitatory synaptic transmission of GLAST1 and GLAST1/EAAC1 deficient mice. Brain Res Mol Brain Res. 2004 Sep 28;128(2):170-81. PubMed PMID: 15363892. 6: Mascias P, Scheede M, Bloms-Funke P, Chizh B. Modulation of spinal nociception by GluR5 kainate receptor ligands in acute and hyperalgesic states and the role of gabaergic mechanisms. Neuropharmacology. 2002 Sep;43(3):327-39. PubMed PMID: 12243762. 7: Schmitz D, Mellor J, Frerking M, Nicoll RA. Presynaptic kainate receptors at hippocampal mossy fiber synapses. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11003-8. Review. PubMed PMID: 11572960; PubMed Central PMCID: PMC58674. 8: Bleakman D, Ogden AM, Ornstein PL, Hoo K. Pharmacological characterization of a GluR6 kainate receptor in cultured hippocampal neurons. Eur J Pharmacol. 1999 Aug 13;378(3):331-7. PubMed PMID: 10493110. 9: Carver JM, Mansson PE, Cortes-Burgos L, Shu J, Zhou LM, Howe JR, Giordano T. Cytotoxic effects of kainate ligands on HEK cell lines expressing recombinant kainate receptors. Brain Res. 1996 May 13;720(1-2):69-74. PubMed PMID: 8782898.