SYM2081

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

MedKoo CAT#: 532799

CAS#: 31137-74-3

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532799
Name: SYM2081
CAS#: 31137-74-3
Chemical Formula: C6H11NO4
Exact Mass: 161.07
Molecular Weight: 161.160
Elemental Analysis: C, 44.72; H, 6.88; N, 8.69; O, 39.71

Price and Availability

Size	Price	Availability
5mg	USD 475	2 Weeks
10mg	USD 740	2 Weeks
25mg	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Water	50.0	310.25

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:	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.
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.

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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.

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