MPEP hydrochloride

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Cat.No. 1212 - MPEP hydrochloride | C14H11N.HCl | CAS No. 219911-35-0
Description: mGlu5 antagonist and positive allosteric modulator at mGlu4
Chemical Name: 2-Methyl-6-(phenylethynyl)pyridine hydrochloride
Purity: ≥99% (HPLC)
Datasheet
Citations (53)
Literature

Biological Activity

Potent and highly selective non-competitive antagonist at the mGlu5 receptor subtype (IC50 = 36 nM) and a positive allosteric modulator at mGlu4 receptors. Centrally active following systemic administration in vivo. Reverses mechanical hyperalgesia in the inflamed rat hind paw. Also available as part of the Group I mGlu Receptor Tocriset™.

Compound Libraries

MPEP hydrochloride is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 229.71
Formula C14H11N.HCl
Storage Desiccate at +4°C
Purity ≥99% (HPLC)
CAS Number 219911-35-0
PubChem ID 9794588
InChI Key PKDHDJBNEKXCBI-UHFFFAOYSA-N
Smiles Cl.CC1=CC=CC(=N1)C#CC1=CC=CC=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 22.97 100
ethanol 22.97 100
water 1.15 5mM with gentle warming

Preparing Stock Solutions

The following data is based on the product molecular weight 229.71. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 4.35 mL 21.77 mL 43.53 mL
5 mM 0.87 mL 4.35 mL 8.71 mL
10 mM 0.44 mL 2.18 mL 4.35 mL
50 mM 0.09 mL 0.44 mL 0.87 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Gasparini et al (1999) 2-Methyl-6-(phenylethynyl)-pyridine (MPEP), a potent, selective and systemically active mGlu5 receptor antagonist. Neuropharmacology 38 1493 PMID: 10530811

Mathiesen et al (2003) Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br.J.Pharmacol. 138 1026 PMID: 12684257

Salt et al (1999) Antagonism of the mGlu5 agonist 2-chloro-5-hydroxyphenylglycine by the novel selective mGlu5 antagonist 6-methyl-2-(phenylethynyl)-pyridine (MPEP) in the thalamus. Br.J.Pharmacol. 127 1057 PMID: 10455248

Bowes et al (1999) Anti-hyperalgesic effects of the novel metabotropic glutamate receptor 5 antagonist, methylphenylethynylpyridine, in rat models of inflammatory pain. Br.J.Pharmacol. 126 250P PMID:


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Keywords: MPEP hydrochloride, supplier, mGlu5, mGluR5, antagonists, positive, allosteric, modulators, mGlu4, mGluR4, PAM, Positive, Group, I, Receptors, Glutamate, Metabotropic, III, Glutamate, (Metabotropic), Group, I, Receptors, Glutamate, (Metabotropic), Group, III, Receptors, Glutamate, (Metabotropic), Group, I, Receptors, Tocris Bioscience

53 Citations for MPEP hydrochloride

Citations are publications that use Tocris products. Selected citations for MPEP hydrochloride include:

David-Pereira (2017) The medullary dorsal reticular nucleus as a relay for descending pronociception induced by the mGluR5 in the rat infralimbic cortex. Neuroscience 349 341 PMID: 28300633

Xi (2017) Metabotropic glutamate receptor 5 mediates the suppressive effect of 6-OHDA-induced model of Parkinson's disease on liver cancer. Pharmacol Res 121 145 PMID: 28455267

Tang and Alger (2015) Homer protein-metabotropic glutamate receptor binding regulates endocannabinoid signaling and affects hyperexcitability in a mouse model of fragile X syndrome. J Neurosci 35 3938 PMID: 25740522

Guimaraes et al (2015) The metabotropic glutamate receptor 5 role on motor behavior involves specific neural substrates. J Biol Chem 8 24 PMID: 25885370

Rook et al (2015) Relationship between in vivo receptor occupancy and efficacy of metabotropic glutamate receptor subtype 5 allosteric modulators with different in vitro binding profiles. Clin Exp Dermatol 40 755 PMID: 25241804

Szokol et al (2015) Augmentation of Ca(2+) signaling in astrocytic endfeet in the latent phase of temporal lobe epilepsy. Int J Mol Sci 9 49 PMID: 25762896

Ko et al (2015) Nerve demyelination increases metabotropic glutamate receptor subtype 5 expression in peripheral painful mononeuropathy. J Neurophysiol 16 4642 PMID: 25739080

Zhong et al (2015) BDNF interacts with endocannabinoids to regulate cocaine-induced synaptic plasticity in mouse midbrain dopamine neurons. J Neurosci 35 4469 PMID: 25762688

Cramer et al (2015) Abnormal excitability and episodic low-frequency oscillations in the cerebral cortex of the tottering mouse. PLoS One 35 5664 PMID: 25855180

Tamura et al (2014) Both neurons and astrocytes exhibited tetrodotoxin-resistant metabotropic glutamate receptor-dependent spontaneous slow Ca2+ oscillations in striatum. PLoS One 9 e85351 PMID: 24454845

Trepanier et al (2013) Group II metabotropic glutamate receptors modify N-methyl-D-aspartate receptors via Src kinase. Sci Rep 3 926 PMID: 23378895

Kumar et al (2013) Effects of the mGluR5 antagonist MPEP on ethanol withdrawal induced anxiety-like syndrome in rats. Behav Brain Funct 9 43 PMID: 24279870

Ramiro-Cortés and Israely (2013) Long lasting protein synthesis- and activity-dependent spine shrinkage and elimination after synaptic depression. PLoS One 8 e71155 PMID: 23951097

Loane et al (2013) Activation of mGluR5 and inhibition of NADPH oxidase improves functional recovery after traumatic brain injury. J Neurosci 30 403 PMID: 23199080

Kuribayashi et al (2013) The role of metabotropic glutamate receptor 5 on the stromal cell-derived factor-1/CXCR4 system in oral cancer. Proc Natl Acad Sci U S A 8 e80773 PMID: 24236200

Mayo et al (2012) Nitrative stress in cerebral endothelium is mediated by mGluR5 in hyperhomocysteinemia. J Cereb Blood Flow Metab 32 825 PMID: 22186670

Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285 PMID: 22368777

Bozdagi et al (2012) Haploinsufficiency of Cyfip1 produces fragile X-like phenotypes in mice. J Neurosci 7 e42422 PMID: 22900020

Crock et al (2012) Central amygdala metabotropic glutamate receptor 5 in the modulation of visceral pain. J Neurotrauma 32 14217 PMID: 23055491

Zhang and Lisman (2012) Activity-dependent regulation of synaptic strength by PSD-95 in CA1 neurons. J Neurosci 107 1058 PMID: 22114157

Halberstadt et al (2011) Interactive effects of mGlu5 and 5-HT2A receptors on locomotor activity in mice. Psychopharmacology (Berl) 215 81 PMID: 21153406

Hays et al (2011) Altered neocortical rhythmic activity states in Fmr1 KO mice are due to enhanced mGluR5 signaling and involve changes in excitatory circuitry. J Neurosci 31 14223 PMID: 21976507

Price et al (2010) Alterations in mGluR5 expression and signaling in Lewy body disease and in transgenic models of alpha-synucleinopathy--implications for excitotoxicity. PLoS One 5 e14020 PMID: 21103359

Jiang et al (2010) The maturation of GABAergic transmission in visual cortex requires endocannabinoid-mediated LTD of inhibitory inputs during a critical period. Neuron 66 248 PMID: 20435001

Gómez-Gonzalo et al (2010) An excitatory loop with astrocytes contributes to drive neurons to seizure threshold. PLoS Biol 8 e1000352 PMID: 20405049

Hammond et al (2010) Discovery of a Novel Chemical Class of mGlu(5) Allosteric Ligands with Distinct Modes of Pharmacology. ACS Chem Neurosci 1 702 PMID: 20981342

Fuortes et al (2010) Distinctions between persistent and reversible group I mGluR-induced epileptiform burst prolongation. Epilepsia 51 1633 PMID: 20659148

Parri et al (2010) Sensory and cortical activation of distinct glial cell subtypes in the somatosensory thalamus of young rats. Eur J Neurosci 32 29 PMID: 20608967

Tronson et al (2010) Metabotropic glutamate receptor 5/Homer interactions underlie stress effects on fear. Front Cell Neurosci 68 1007 PMID: 21075228

Kolber et al (2010) Activation of metabotropic glutamate receptor 5 in the amygdala modulates pain-like behavior. PLoS One 30 8203 PMID: 20554871

Lee and Sherman (2009) Modulator property of the intrinsic cortical projection from layer 6 to layer 4. Front Syst Neurosci 3 3 PMID: 19277215

Shen et al (2008) Dichotomous dopaminergic control of striatal synaptic plasticity. Science 321 848 PMID: 18687967

Zhang et al (2008) The tyrosine phosphatase STEP mediates AMPA receptor endocytosis after metabotropic glutamate receptor stimulation. J Neurosci 28 10561 PMID: 18923032

Neyman and Manahan-Vaughan (2008) Metabotropic glutamate receptor 1 (mGluR1) and 5 (mGluR5) regulate late phases of LTP and LTD in the hippocampal CA1 region in vitro. Eur J Neurosci 27 1345 PMID: 18364018

Kim et al (2008) Aberrant early-phase ERK inactivation impedes neuronal function in fragile X syndrome. J Neurosci 105 4429 PMID: 18332424

Petzold et al (2008) Coupling of neural activity to blood flow in olfactory glomeruli is mediated by astrocytic pathways. Neuropharmacology 58 897 PMID: 18579080

Kirschstein et al (2007) Loss of metabotropic glutamate receptor-dependent long-term depression via downregulation of mGluR5 after status epilepticus. J Neurosci 27 7696 PMID: 17634364

Xu et al (2007) Calpain-mediated mGluR1alpha truncation: a key step in excitotoxicity. Neuron 53 399 PMID: 17270736

Muddashetty et al (2007) Dysregulated metabotropic glutamate receptor-dependent translation of AMPA receptor and postsynaptic density-95 mRNAs at synapses in a mouse model of fragile X syndrome. J Neurosci 27 5338 PMID: 17507556

Nakamoto et al (2007) Fragile X mental retardation protein deficiency leads to excessive mGluR5-dependent internalization of AMPA receptors. Proc Natl Acad Sci U S A 104 15537 PMID: 17881561

Sossa et al (2007) AMPAR exocytosis through NO modulation of PICK1. Biol Psychiatry 53 92 PMID: 17555774

Bäckström and Hyytiä (2006) Ionotropic and metabotropic glutamate receptor antagonism attenuates cue-induced cocaine seeking. Neuropsychopharmacology 31 778 PMID: 16123768

Keuren-Jensen and Cline (2006) Visual experience regulates metabotropic glutamate receptor-mediated plasticity of AMPA receptor synaptic transmission by homer1a induction. J Neurosci 26 7575 PMID: 16855085

Rancillac et al (2006) Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum. Neuron 26 6997 PMID: 16807329

Calò et al (2005) Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons. J Neurosci 25 2245 PMID: 15745950

Jong et al (2005) Functional metabotropic glutamate receptors on nuclei from brain and primary cultured striatal neurons. Role of transporters in delivering ligand. Mol Pharmacol 280 30469 PMID: 15958386

Jung et al (2005) Stimulation of endocannabinoid formation in brain slice cultures through activation of group I metabotropic glutamate receptors. Neuropsychopharmacology 68 1196 PMID: 16051747

Chevaleyre and Castillo (2004) Endocannabinoid-mediated metaplasticity in the hippocampus. Neuron 43 871 PMID: 15363397

Gallagher et al (2004) Extracellular signal-regulated protein kinase activation is required for metabotropic glutamate receptor-dependent long-term depression in hippocampal area CA1. Mol Brain 24 4859 PMID: 15152046

Mathiesen et al (2003) Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br J Pharmacol 138 1026 PMID: 12684257

Nishi et al (2003) Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling. J Neurosci 100 1322 PMID: 12538871

Takata and Hirase Cortical layer 1 and layer 2/3 astrocytes exhibit distinct calcium dynamics in vivo. PLoS One 3 e2525 PMID: 18575586

Lafourcade et al Molecular components and functions of the endocannabinoid system in mouse prefrontal cortex. PLoS One 2 e709 PMID: 17684555


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