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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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