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:
Molecular Weight:
161.16
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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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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)
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