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G137

Sigma-Aldrich

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

solid

Sinônimo(s):

SYM-2081

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About This Item

Fórmula empírica (Notação de Hill):
C6H11NO4
Número CAS:
31137-74-3
Peso molecular:
161.16
Número MDL:
MFCD00937765
Código UNSPSC:
12352200
ID de substância PubChem:
24895059

Formulário

solid

atividade óptica

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

cor

white

solubilidade

H2O: >10 mg/mL

cadeia de caracteres SMILES

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

chave InChI

KRKRAOXTGDJWNI-DMTCNVIQSA-N

Informações sobre genes

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

Aplicação

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

Ações bioquímicas/fisiológicas

(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.

Código de classe de armazenamento

13 - Non Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (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)
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 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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