(RS)-MCPGA non-selective group I/group II metabotropic glutamate receptor antagonist

(RS)-MCPG (CAS 146669-29-6)

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Synonym: (±)-α-Methyl-(4-carboxyphenyl)glycine
Application: A non-selective group I/group II metabotropic glutamate receptor antagonist
CAS Number: 146669-29-6
Purity: ≥97%
Molecular Weight: 209.2
Molecular Formula: C10H11NO4
* Refer to Certificate of Analysis for lot specific data (including water content).
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(RS)-MCPG, or (RS)-alpha-methyl-4-carboxyphenylglycine, is a non-selective antagonist of group I/II metabotropic glutamate receptors (mGluR). (RS)-MCPG is employed as a tool for probing the mGluR system and elucidating the role of mGluRs in biological processes. (RS)-MCPG is described to block spatial learning in rats through interaction at the group I mGluR. (RS)-MCPG was also used as a tool to demonstrate that synaptic activation of mGluR is necessary for the induction of long-term potentiation in the hippocampus. The isomer (S)-MCPG (sc-202329) is described to be the active isomer of the (RS)-MCPG preparation. (RS)-MCPG is an inhibitor of mGluR-1a, mGluR-1b, mGluR-2, mGluR-3 and mGluR-5.


References

1. Eaton, S.A., et al. 1993. Eur. J. Pharmacol. 244: 195-197. PMID: 8381746
2. Bashir, Z.I., et al. 1993. Nature. 363: 347-350. PMID: 8388549
3. O'Connor, J.J., et al. 1994. Nature. 367: 557-559. PMID: 7906392
4. Joly, C., et al. 1995. J. Neurosci. 15: 3970-3981. PMID: 7751958
5. Wilson, C., et al. 1997. Acta Crystallogr C. 53: 909-911. PMID: 9241811
6. Martin, S.J. and Morris, R.G. 1997. Neuropharmacology. 36: 1339-1354. PMID: 9423922
7. Breakwell, N.A., et al. 1998. J. Neurophysiol. 79: 1270-1276. PMID: 9497408
8. Kim, J.H. and Vezina, P. 1998. Neuropharmacology. 37: 189-197. PMID: 9680243
9. Balschun, D. and Wetzel, W. 1998. Neurosci. Lett. 249: 41-44. PMID: 9672384

Physical State :
Solid
Solubility :
Soluble in 1.1eq. NaOH (100 mM), and dilute aqueous base. Insoluble in water, ethanol, and DMSO.
Storage :
Store at room temperature
Melting Point :
296.34° C (Predicted)
Boiling Point :
~425.3° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.61 (Predicted)
IC50 :
mGluR-2: IC50 = 50 µM (human); PLC β1: IC50 = 150 µM (human); mGluR-1: IC50 = 155 µM (human); mGluR-3: IC50 = 270 µM (human); mGluR-4: IC50 >1000 µM (human)
Ki Data :
mGluR-1: Ki= 50 µM (human); mGluR-2: Ki= 51 µM (human); mGluR-4: Ki>1000 µM (human); mGluR-5: Ki= >2000 µM (human)
pK Values :
pKa: 1.76 (Predicted), pKb: 9.97 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
1222
MDL Number :
MFCD00210205
SMILES :
CC(C1=CC=C(C=C1)C(=O)O)(C(=O)O)N

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Certificate of Analysis

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