Catalog Number: 1212
Chemical Name: 2-Methyl-6-(phenylethynyl)pyridine hydrochloride
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™.
Technical Data
  • M.Wt:
    229.71
  • Formula:
    C14H11N.HCl
  • Solubility:
    Soluble to 5 mM in water with gentle warming and to 100 mM in DMSO
  • Purity:
    >99%
  • Storage:
    Desiccate at +4°C
  • CAS No:
    219911-35-0
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.
Background References
  1. Synthesis of S-[3-(4(5)-imidazolyl)propyl]-N-[2-(4-[125I]-iodophenylethyl]isothiourea sulfate [125I]-iodophenpropit), a new probe for histamine H3 receptor binding sites.
    Menge et al.
    J.Labelled Comp.Radiopharm. XXXI, 1992;10:781
  2. 2-Methyl-6-(phenylethynyl)-pyridine (MPEP), a potent, selective and systemically active mGlu5 receptor antagonist.
    Gasparini et al.
    Neuropharmacology, 1999;38:1493
  3. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP.
    Mathiesen et al.
    Br.J.Pharmacol., 2003;138:1026
  4. Antagonism of the mGlu5 agonist 2-chloro-5-hydroxyphenylglycine by the novel selective mGlu5 antagonist 6-methyl-2-(phenylethynyl)-pyridine (MPEP) in the thalamus.
    Salt et al.
    Br.J.Pharmacol., 1999;127:1057
Citations:

The citations listed below are publications that use Tocris products. Selected citations for MPEP hydrochloride include:

53 Citations: Showing 1 - 10
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  1. Cortical layer 1 and layer 2/3 astrocytes exhibit distinct calcium dynamics in vivo.
    Authors: Takata and Hirase
    PLoS One ;3:e2525
  2. Molecular components and functions of the endocannabinoid system in mouse prefrontal cortex.
    Authors: Lafourcade Et al.
    PLoS One ;2:e709
  3. The medullary dorsal reticular nucleus as a relay for descending pronociception induced by the mGluR5 in the rat infralimbic cortex.
    Authors: David-Pereira
    Neuroscience 2017;349:341
  4. Metabotropic glutamate receptor 5 mediates the suppressive effect of 6-OHDA-induced model of Parkinson's disease on liver cancer.
    Authors: Xi
    Pharmacol Res 2017;121:145
  5. Augmentation of Ca(2+) signaling in astrocytic endfeet in the latent phase of temporal lobe epilepsy.
    Authors: Szokol Et al.
    Int J Mol Sci 2015;9:49
  6. The metabotropic glutamate receptor 5 role on motor behavior involves specific neural substrates.
    Authors: Guimaraes Et al.
    J Biol Chem 2015;8:24
  7. Relationship between in vivo receptor occupancy and efficacy of metabotropic glutamate receptor subtype 5 allosteric modulators with different in vitro binding profiles.
    Authors: Rook Et al.
    Clin Exp Dermatol 2015;40:755
  8. Abnormal excitability and episodic low-frequency oscillations in the cerebral cortex of the tottering mouse.
    Authors: Cramer Et al.
    PLoS One 2015;35:5664
  9. BDNF interacts with endocannabinoids to regulate cocaine-induced synaptic plasticity in mouse midbrain dopamine neurons.
    Authors: Zhong Et al.
    J Neurosci 2015;35:4469
  10. Homer protein-metabotropic glutamate receptor binding regulates endocannabinoid signaling and affects hyperexcitability in a mouse model of fragile X syndrome.
    Authors: Tang and Alger
    J Neurosci 2015;35:3938
  11. Nerve demyelination increases metabotropic glutamate receptor subtype 5 expression in peripheral painful mononeuropathy.
    Authors: Ko Et al.
    J Neurophysiol 2015;16:4642
  12. Both neurons and astrocytes exhibited tetrodotoxin-resistant metabotropic glutamate receptor-dependent spontaneous slow Ca2+ oscillations in striatum.
    Authors: Tamura Et al.
    PLoS One 2014;9:e85351
  13. Effects of the mGluR5 antagonist MPEP on ethanol withdrawal induced anxiety-like syndrome in rats.
    Authors: Kumar Et al.
    Behav Brain Funct 2013;9:43
  14. The role of metabotropic glutamate receptor 5 on the stromal cell-derived factor-1/CXCR4 system in oral cancer.
    Authors: Kuribayashi Et al.
    Proc Natl Acad Sci U S A 2013;8:e80773
  15. Long lasting protein synthesis- and activity-dependent spine shrinkage and elimination after synaptic depression.
    Authors: Ramiro-Cortés and Israely
    PLoS One 2013;8:e71155
  16. Group II metabotropic glutamate receptors modify N-methyl-D-aspartate receptors via Src kinase.
    Authors: Trepanier Et al.
    Sci Rep 2013;3:926
  17. Activation of mGluR5 and inhibition of NADPH oxidase improves functional recovery after traumatic brain injury.
    Authors: Loane Et al.
    J Neurosci 2013;30:403
  18. Haploinsufficiency of Cyfip1 produces fragile X-like phenotypes in mice.
    Authors: Bozdagi Et al.
    J Neurosci 2012;7:e42422
  19. Nitrative stress in cerebral endothelium is mediated by mGluR5 in hyperhomocysteinemia.
    Authors: Mayo Et al.
    J Cereb Blood Flow Metab 2012;32:825
  20. Central amygdala metabotropic glutamate receptor 5 in the modulation of visceral pain.
    Authors: Crock Et al.
    J Neurotrauma 2012;32:14217
  21. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep 2012;2:285
  22. Activity-dependent regulation of synaptic strength by PSD-95 in CA1 neurons.
    Authors: Zhang and Lisman
    J Neurosci 2012;107:1058
  23. Altered neocortical rhythmic activity states in Fmr1 KO mice are due to enhanced mGluR5 signaling and involve changes in excitatory circuitry.
    Authors: Hays Et al.
    J Neurosci 2011;31:14223
  24. Interactive effects of mGlu5 and 5-HT2A receptors on locomotor activity in mice.
    Authors: Halberstadt Et al.
    Psychopharmacology (Berl) 2011;215:81
  25. An excitatory loop with astrocytes contributes to drive neurons to seizure threshold.
    Authors: Gómez-Gonzalo Et al.
    PLoS Biol 2010;8:e1000352
  26. Metabotropic glutamate receptor 5/Homer interactions underlie stress effects on fear.
    Authors: Tronson Et al.
    Front Cell Neurosci 2010;68:1007
  27. The maturation of GABAergic transmission in visual cortex requires endocannabinoid-mediated LTD of inhibitory inputs during a critical period.
    Authors: Jiang Et al.
    Neuron 2010;66:248
  28. Alterations in mGluR5 expression and signaling in Lewy body disease and in transgenic models of alpha-synucleinopathy--implications for excitotoxicity.
    Authors: Price Et al.
    PLoS One 2010;5:e14020
  29. Distinctions between persistent and reversible group I mGluR-induced epileptiform burst prolongation.
    Authors: Fuortes Et al.
    Epilepsia 2010;51:1633
  30. Sensory and cortical activation of distinct glial cell subtypes in the somatosensory thalamus of young rats.
    Authors: Parri Et al.
    Eur J Neurosci 2010;32:29
  31. Activation of metabotropic glutamate receptor 5 in the amygdala modulates pain-like behavior.
    Authors: Kolber Et al.
    PLoS One 2010;30:8203
  32. Discovery of a Novel Chemical Class of mGlu(5) Allosteric Ligands with Distinct Modes of Pharmacology.
    Authors: Hammond Et al.
    ACS Chem Neurosci 2010;1:702
  33. Modulator property of the intrinsic cortical projection from layer 6 to layer 4.
    Authors: Lee and Sherman
    Front Syst Neurosci 2009;3:3
  34. Coupling of neural activity to blood flow in olfactory glomeruli is mediated by astrocytic pathways.
    Authors: Petzold Et al.
    Neuropharmacology 2008;58:897
  35. Dichotomous dopaminergic control of striatal synaptic plasticity.
    Authors: Shen Et al.
    Science 2008;321:848
  36. The tyrosine phosphatase STEP mediates AMPA receptor endocytosis after metabotropic glutamate receptor stimulation.
    Authors: Zhang Et al.
    J Neurosci 2008;28:10561
  37. Metabotropic glutamate receptor 1 (mGluR1) and 5 (mGluR5) regulate late phases of LTP and LTD in the hippocampal CA1 region in vitro.
    Authors: Neyman and Manahan-Vaughan
    Eur J Neurosci 2008;27:1345
  38. Aberrant early-phase ERK inactivation impedes neuronal function in fragile X syndrome.
    Authors: Kim Et al.
    J Neurosci 2008;105:4429
  39. AMPAR exocytosis through NO modulation of PICK1.
    Authors: Sossa Et al.
    Biol Psychiatry 2007;53:92
  40. Calpain-mediated mGluR1alpha truncation: a key step in excitotoxicity.
    Authors: Xu Et al.
    Neuron 2007;53:399
  41. Loss of metabotropic glutamate receptor-dependent long-term depression via downregulation of mGluR5 after status epilepticus.
    Authors: Kirschstein Et al.
    J Neurosci 2007;27:7696
  42. Dysregulated metabotropic glutamate receptor-dependent translation of AMPA receptor and postsynaptic density-95 mRNAs at synapses in a mouse model of fragile X syndrome.
    Authors: Muddashetty Et al.
    J Neurosci 2007;27:5338
  43. Fragile X mental retardation protein deficiency leads to excessive mGluR5-dependent internalization of AMPA receptors.
    Authors: Nakamoto Et al.
    Proc Natl Acad Sci U S A 2007;104:15537
  44. Ionotropic and metabotropic glutamate receptor antagonism attenuates cue-induced cocaine seeking.
    Authors: Bäckström and Hyytiä
    Neuropsychopharmacology 2006;31:778
  45. Visual experience regulates metabotropic glutamate receptor-mediated plasticity of AMPA receptor synaptic transmission by homer1a induction.
    Authors: Keuren-Jensen and Cline
    J Neurosci 2006;26:7575
  46. Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum.
    Authors: Rancillac Et al.
    Neuron 2006;26:6997
  47. Stimulation of endocannabinoid formation in brain slice cultures through activation of group I metabotropic glutamate receptors.
    Authors: Jung Et al.
    Neuropsychopharmacology 2005;68:1196
  48. Functional metabotropic glutamate receptors on nuclei from brain and primary cultured striatal neurons. Role of transporters in delivering ligand.
    Authors: Jong Et al.
    Mol Pharmacol 2005;280:30469
  49. Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons.
    Authors: Calò Et al.
    J Neurosci 2005;25:2245
  50. Endocannabinoid-mediated metaplasticity in the hippocampus.
    Authors: Chevaleyre and Castillo
    Neuron 2004;43:871
  51. Extracellular signal-regulated protein kinase activation is required for metabotropic glutamate receptor-dependent long-term depression in hippocampal area CA1.
    Authors: Gallagher Et al.
    Mol Brain 2004;24:4859
  52. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP.
    Authors: Mathiesen Et al.
    Br J Pharmacol 2003;138:1026
  53. Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling.
    Authors: Nishi Et al.
    J Neurosci 2003;100:1322
Expand to show all 53 Citations
Average Rating: 5 (Based on 1 review)

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