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Merck
CN

G137

(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
UNSPSC Code:
12352200
PubChem Substance ID:
24895059
MDL number:
MFCD00937765

Key Documents

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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.

Biochem/physiol Actions

(2S,4R)-4-Methylglutamic acid (SYM 2081) is a selective antagonist for the kainate receptor that elicits antihyperalgesic and antinociceptive functionality. 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. It may also be involved in the attenuation of heat hyperalgesia in nerve injury models.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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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
N J Toms et al.
Neuropharmacology, 36(11-12), 1483-1488 (1998-03-28)
Since kainate evokes large non-desensitizing currents at alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors, kainate is of limited use in discriminating between AMPA and kainate receptors. Following recent reports that (2S,4R)-4-methylglutamate is a kainate receptor-selective agonist, we have radiolabelled and subsequently characterized the
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
L E Ta et al.
Brain research, 858(1), 106-120 (2000-03-04)
Cold-freeze injury at -4 degrees C to the rat sciatic nerve produces mechanical allodynia and thermal hyperalgesia [M.A. Kleive, P.S. Jungbluth, J.A. Uhlenkamp, K.C. Kajander, Cold injury to rat sciatic nerve induces thermal hyperalgesia or analgesia, 8th World Congress on
Michelle S Turner et al.
Brain research, 973(2), 252-264 (2003-05-10)
Excitatory amino acids acting at non-NMDA receptors contribute to transmission of nociceptive information. SYM 2081 ((2S,4R)-4-methyl glutamic acid) desensitizes kainate receptors, one subtype of non-NMDA receptors, to subsequent release of excitatory amino acids and thus may attenuate transmission of nociceptive
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