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Merck

G137

Sigma-Aldrich

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

solid

Sinónimos:

SYM-2081

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About This Item

Fórmula empírica (notación de Hill):
C6H11NO4
Número de CAS:
Peso molecular:
161.16
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
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
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

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