Catalog Number: 0342
Chemical Name: (RS)-3,5-Dihydroxyphenylglycine
Biological Activity
Selective group I metabotropic glutamate receptor agonist which activates both mGlu1 and mGlu5. Also reported to be an antagonist at metabotropic glutamate receptors linked to phospholipase D.

S-enantiomer also available.

Technical Data
  • M.Wt:
    183.16
  • Formula:
    C8H9NO4
  • Solubility:
    Soluble to 10 mM in water
  • Purity:
    >99%
  • Storage:
    Desiccate at -20°C
  • CAS No:
    19641-83-9
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.
Additional Information
Other Product-Specific Information:
Background References
  1. 3,5-Dihydroxyphenylglycine: a potent agonist of metabotropic glutamate receptors.
    Ito et al.
    NeuroReport, 1992;3:1013
  2. Regulation of phosphoinositide turnover in neonatal rat cerebral cortex by group I- and II-selective metabotropic glutamate receptor agonists.
    Mistry et al.
    Br.J.Pharmacol., 1998;123:581
  3. The group I mGlu receptor agonist DHPG induces a novel form of LTD in the CA1 region of the hippocampus.
    Palmer et al.
    Neuropharmacology, 1997;36:1517
  4. Pharmacological characterization of metabotropic glutamate recpetors coupled to phopholipase D in the rat hippocampus.
    Pellegrini-Giampietro et al.
    Br.J.Pharmacol., 1996;118:1035
Citations:

The citations listed below are publications that use Tocris products. Selected citations for (RS)-3,5-DHPG include:

40 Citations: Showing 1 - 10
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  1. 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
  2. Colocalization of neurotransmitter transporters on the plasma membrane of the same nerve terminal may reflect cotransmission.
    Authors: Romei Et al.
    Brain Research Bulletin 2016;127:100
  3. Neuronal splicing regulator RBFOX3(NeuN) regulates adult hippocampal neurogenesis and synaptogenesis
    Authors: Lin Et al.
    PLoS One 2016;11:e0164164
  4. Dendritic spine dynamics leading to spine elimination after repeated inductions of LTD.
    Authors: Hasegawa Et al.
    J Neurosci 2015;5:7707
  5. BDNF interacts with endocannabinoids to regulate cocaine-induced synaptic plasticity in mouse midbrain dopamine neurons.
    Authors: Zhong Et al.
    Sci Rep 2015;35:4469
  6. PDE-4 inhibition rescues aberrant synaptic plasticity in Drosophila and mouse models of fragile X syndrome.
    Authors: Choi Et al.
    Proc Natl Acad Sci U S A 2015;35:396
  7. Rapid manifestation of reactive astrogliosis in acute hippocampal brain slices.
    Authors: Takano Et al.
    Glia 2014;62:78
  8. Long-term depression-inducing stimuli promote cleavage of the synaptic adhesion molecule NGL-3 through NMDA receptors, matrix metalloproteinases and presenilin/γ-secretase.
    Authors: Lee Et al.
    Philos Trans R Soc Lond B Biol Sci 2014;369:20130158
  9. Involvement of TrkB- and p75(NTR)-signaling pathways in two contrasting forms of long-lasting synaptic plasticity.
    Authors: Sakuragi Et al.
    J Vis Exp 2013;3:3185
  10. Modulation of mGluR-dependent MAP1B translation and AMPA receptor endocytosis by microRNA miR-146a-5p.
    Authors: Chen and Shen
    J Neurosci 2013;33:9013
  11. Simultaneous monitoring of presynaptic transmitter release and postsynaptic receptor trafficking reveals an enhancement of presynaptic activity in metabotropic glutamate receptor-mediated long-term depression.
    Authors: Xu Et al.
    J Neurosci 2013;33:5867
  12. Impaired activity-dependent FMRP translation and enhanced mGluR-dependent LTD in Fragile X premutation mice.
    Authors: Iliff Et al.
    Hum Mol Genet 2013;22:1180
  13. The plasma membrane Ca2+-ATPase2 (PMCA2) is involved in the regulation of Purkinje cell dendritic growth in cerebellar organotypic slice cultures.
    Authors: Sherkhane and Kapfhammer
    J Neurosci 2013;2013:321685
  14. The analysis of purkinje cell dendritic morphology in organotypic slice cultures.
    Authors: Kapfhammer and Gugger
    J Neurosci 2012;NULL
  15. Central amygdala metabotropic glutamate receptor 5 in the modulation of visceral pain.
    Authors: Crock Et al.
    Eur J Neurosci 2012;32:14217
  16. MeCP2 phosphorylation is required for modulating synaptic scaling through mGluR5.
    Authors: Zhong Et al.
    Stem Cell Reports 2012;32:12841
  17. Activity Modes in Thalamocortical Relay Neurons are Modulated by G(q)/G(11) Family G-proteins - Serotonergic and Glutamatergic Signaling.
    Authors: Coulon Et al.
    Front Cell Neurosci 2011;4:132
  18. Loss of Tsc1 in vivo impairs hippocampal mGluR-LTD and increases excitatory synaptic function.
    Authors: Bateup Et al.
    Neurosci Lett 2011;31:8862
  19. 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
  20. Activation of metabotropic glutamate receptor 5 in the amygdala modulates pain-like behavior.
    Authors: Kolber Et al.
    Sci Rep 2010;30:8203
  21. Group II metabotropic glutamate receptor stimulation triggers production and release of Alzheimer's amyloid(β)42 from isolated intact nerve terminals.
    Authors: Kim Et al.
    J Neurosci 2010;30:3870
  22. Neuroligin 1 is dynamically exchanged at postsynaptic sites.
    Authors: Schapitz Et al.
    J Neurosci 2010;30:12733
  23. Converging signal on ERK1/2 activity regulates group I mGluR-mediated Arc transcription.
    Authors: Wang Et al.
    J Neurosci 2009;460:36
  24. N-methyl-D-aspartate receptor- and metabotropic glutamate receptor-dependent long-term depression are differentially regulated by the ubiquitin-proteasome system.
    Authors: Citri Et al.
    J Neurosci 2009;30:1443
  25. Fast subplasma membrane Ca2+ transients control exo-endocytosis of synaptic-like microvesicles in astrocytes.
    Authors: Marchaland Et al.
    J Neurosci 2008;28:9122
  26. The tyrosine phosphatase STEP mediates AMPA receptor endocytosis after metabotropic glutamate receptor stimulation.
    Authors: Zhang Et al.
    J Neurosci 2008;28:10561
  27. Aberrant early-phase ERK inactivation impedes neuronal function in fragile X syndrome.
    Authors: Kim Et al.
    J Neurosci 2008;105:4429
  28. 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
  29. Disynaptic amplification of metabotropic glutamate receptor 1 responses in the olfactory bulb.
    Authors: Jan and Westbrook
    J Neurosci 2007;27:132
  30. Vesicular release of glutamate from unmyelinated axons in white matter.
    Authors: Ziskin Et al.
    Proc Natl Acad Sci U S A 2007;10:321
  31. A role in learning for SRF: deletion in the adult forebrain disrupts LTD and the formation of an immediate memory of a novel context.
    Authors: Etkin Et al.
    Neuron 2006;50:127
  32. 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
  33. Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum.
    Authors: Rancillac Et al.
    J Neurosci 2006;26:6997
  34. Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons.
    Authors: Calò Et al.
    J Neurosci 2005;25:2245
  35. Extracellular signal-regulated protein kinase activation is required for metabotropic glutamate receptor-dependent long-term depression in hippocampal area CA1.
    Authors: Gallagher Et al.
    Neural Plast 2004;24:4859
  36. Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling.
    Authors: Nishi Et al.
    J Neurosci 2003;100:1322
  37. Altered synaptic plasticity in a mouse model of fragile X mental retardation.
    Authors: Huber Et al.
    Proc Natl Acad Sci U S A 2002;99:7746
  38. Neutrophil-derived glutamate regulates vascular endothelial barrier function.
    Authors: Collard Et al.
    J Biol Chem 2002;277:14801
  39. Identification of sites for exponential translation in living dendrites.
    Authors: Job and Eberwine
    Proc Natl Acad Sci U S A 2001;98:13037

Expand to show all 40 Citations
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(S)-3,5-DHPG

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Other Experimental Details

Other Experimental Details(RS)-3,5-DHPG is light and air sensitive and is not stable in alkaline solutions. It is best to use aliquots within a week. Aliquots should not have a brown coloration under proper storage conditions.

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