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M196

Sigma-Aldrich

(+)-α-Methyl-4-carboxyphenylglycine

solid

Synonym(s):

(+)-MCPG, S(+)-α-Amino-4-carboxy-α-methyl-benzeneacetic acid

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About This Item

Empirical Formula (Hill Notation):
C10H11NO4
CAS Number:
150145-89-4
Molecular Weight:
209.20
MDL number:
MFCD00216858
UNSPSC Code:
12352209
PubChem Substance ID:
24896589
NACRES:
NA.32

form

solid

optical activity

[α]20/D +89.54°, c = 0.33 in 6 M HCl(lit.)

solubility

0.1 M NaOH: 15 mg/mL

SMILES string

C[C@@](N)(C(O)=O)c1ccc(cc1)C(O)=O

InChI

1S/C10H11NO4/c1-10(11,9(14)15)7-4-2-6(3-5-7)8(12)13/h2-5H,11H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1

InChI key

DNCAZYRLRMTVSF-JTQLQIEISA-N

Gene Information

rat ... Grm1(24414)

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Application

Active enantiomer of (±)-MCPG

Biochem/physiol Actions

(+)-α-Methyl-4-carboxyphenylglycine, also known as MCPG, is a competitive metabotropic glutamate receptor antagonist.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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(R,S)-alpha-methyl-4-carboxyphenylglycine (MCPG) fails to block long-term potentiation under urethane anaesthesia in vivo.
Martin SJ and Morris RG1
Neuropharmacology, 36(10), 1339-1354 (1997)
G Riedel et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 15(1 Pt 1), 87-98 (1995-01-01)
Metabotropic glutamate receptors (mGluRs) are critically involved in the maintenance of long-term potentiation (LTP) (Reymann and Matthies, 1989; Behnisch et al., 1991; Izumi et al., 1991; Bashir et al., 1993). In order to assess further the physiological role of MGluRs
D E Jane et al.
Neuropharmacology, 32(7), 725-727 (1993-07-01)
The (+)-enantiomer of alpha-methyl-4-carboxyphenylglycine (MCPG) stereoslectively antagonized the depolarization of neonatal rat motoneurones and the excitation of rat thalamic neurons induced by the specific metabotropic glutamate receptor agonist (1S,3R)-1-aminocyclopentane-1,3-dicarboxylate (ACPD). (+)-MCPG preferentially reduced (1S,3R)-ACPD-induced responses relative to responses induced by

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