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G137

Sigma-Aldrich

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

solid

Synonym(s):

SYM-2081

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About This Item

Empirical Formula (Hill Notation):
C6H11NO4
CAS Number:
31137-74-3
Molecular Weight:
161.16
MDL number:
MFCD00937765
UNSPSC Code:
12352200
PubChem Substance ID:
24895059

form

solid

optical activity

[α]23/D +23.2°, c = 0.73 in 6 M HCl(lit.)

color

white

solubility

H2O: >10 mg/mL

SMILES string

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

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

InChI key

KRKRAOXTGDJWNI-DMTCNVIQSA-N

Gene Information

human ... GRIK1(2897) , GRIK2(2898) , SLC1A1(6505) , SLC1A2(6506)
rat ... Gria1(50592) , Grik1(29559) , Grin2a(24409) , Slc1a2(29482)

Application

(2S,4R)-4-Methylglutamic acid has been used as a kainate receptor (KAR) antagonist to test its effect on acetylcholine release in muscle cells.[1]

Biochem/physiol Actions

(2S,4R)-4-Methylglutamic acid (SYM 2081) is a selective antagonist for the kainate receptor[2] that elicits antihyperalgesic and antinociceptive functionality.[2] It may be useful to treat mechanical allodynia associated with the cold-freeze injury model. SYM 2081 also mediates the suppression of glutamate release from injured C-fibers.[3] It may also be involved in the attenuation of heat hyperalgesia in nerve injury models.[2]

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBW6501V
MKBW4299V
SLBG0276V
SLBC8963V
SLBB8506V

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Keith J Todd et al.
Journal of neurophysiology, 91(2), 828-840 (2004-02-06)
The development and function of the vertebrate neuromuscular junction (NMJ) is continually being redefined. Previous studies have indicated that glutamate may play a role in the development or function of the NMJ by associating with presynaptic receptors. We have used
Mariia S Shypshyna et al.
Neuroscience letters, 585, 1-5 (2014-12-03)
The role of Ca(2+)-permeable AMPA-receptors (CP-AMPARs) in the induction of paired-pulse depression (PPD) at glutamatergic nociceptive sensory synapses was examined in co-culture of rat's dorsal root ganglion and dorsal horn neurons. CP-AMPARs make a considerable contribution to excitatory postsynaptic currents
T Minami et al.
Brain research, 895(1-2), 178-185 (2001-03-22)
Glutamate is the main excitatory neurotransmitter in the central nervous system and has been shown to be involved in spinal nociceptive processing. We previously demonstrated that intrathecal (i.t.) administration of prostaglandin (PG) E(2) and PGF(2 alpha) induced touch-evoked pain (allodynia)
K A Jones et al.
Neuropharmacology, 36(6), 853-863 (1997-06-01)
The potencies of kainate, glutamate and diastereomers of 4-methylglutamate were determined for activation and steady-state desensitization of GluR6 and dorsal root ganglion-type kainate receptors using whole-cell voltage clamp. In HEK293 cells expressing GluR6, all four diastereomers induced desensitizing inward currents
L M Zhou et al.
The Journal of pharmacology and experimental therapeutics, 280(1), 422-427 (1997-01-01)
Glutamic acid activates ionotropic glutamate receptors that mediate excitatory transmission in the central nervous system. The introduction of a methyl group at position 4 of glutamic acid imparts selectivity for kainate receptors, relative to other (N-methyl-D-aspartate and alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) ionotropic
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