Home / Group I mGluR Agonists / (RS)-3,5-DHPG

(RS)-3,5-DHPG

Catalog #: 0342
69 Citations 2 Reviews Datasheet / COA / SDS
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0342/10
0342/50
0342/1
(RS)-3,5-DHPG | CAS No. 146255-66-5 | Group I mGluR Agonists
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Description: Selective group I mGlu agonist

Chemical Name: (RS)-3,5-Dihydroxyphenylglycine

Purity: ≥99%

Product Details
Citations (69)
Supplemental Products
Reviews (2)
Biological Activity Technical Data Additional Information Background Product Datasheets Calculators

Biological Activity

(RS)-3,5-DHPG is a 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:
146255-66-5

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Additional Information

Other Product-Specific Information:

Background References

  1. Sapap3 deletion anomalously activates short-term endocannabinoid-mediated synaptic plasticity.
    Chen, Meng, Wan, Yehong, Ade, Kristen, Ting, Jonathan, Feng, Guoping, Calakos, Nicole
    J Neurosci, 2011;31(26):9563-73.
  2. High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death.
    Fox JT, Sakamuru S, Huang R
    Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8.
  3. N-acetylcysteine protects against apoptosis through modulation of group I metabotropic glutamate receptor activity.
    Sun L, Gu L, Wang S
    PLoS ONE, 2012;7(3):e32503.
  4. The MNK - eIF4E signaling axis contributes to injury-induced nociceptive plasticity and the development of chronic pain
    JK Moy, A Khoutorsky, MN Asiedu, BJ Black, JL Kuhn, P Barragán-I, S Megat, MD Burton, CC Burgos-Veg, OK Melemedjia, S Boitano, J Vagner, CG Gkogkas, JJ Pancrazio, JS Mogil, G Dussor, N Sonenberg, TJ Price
    J. Neurosci., 2017;0(0):.
  5. Type 1 metabotropic glutamate receptors (mGlu1) trigger the gating of GluD2 delta glutamate receptors.
    Ady V, Perroy J, Tricoire L, Piochon C, Dadak S, Chen X, Dusart I, Fagni L, Lambolez B, Levenes C
    EMBO Rep, 2014;15(1):103-9.
  6. Roles of CREB in the regulation of FMRP by group I metabotropic glutamate receptors in cingulate cortex.

    Mol Brain, 2012;5(0):27.
  7. 3,5-Dihydroxyphenylglycine: a potent agonist of metabotropic glutamate receptors.
    Ito et al.
    NeuroReport, 1992;3:1013
  8. Pharmacological characterization of metabotropic glutamate recpetors coupled to phopholipase D in the rat hippocampus.
    Pellegrini-Giampietro et al.
    Br.J.Pharmacol., 1996;118:1035
  9. 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
  10. 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

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Citations for (RS)-3,5-DHPG

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

69 Citations: Showing 1 - 10

  1. The Temporal Dynamics of Arc Expression Regulate Cognitive Flexibility.
    Authors: Wall Et al.
    Neuron  2018;98:1124
  2. Neuronal Activity-Dependent Activation of Astroglial Calcineurin in Mouse Primary Hippocampal Cultures.
    Authors: Lim Et al.
    Int J Mol Sci  2018;19
  3. Drebrin Isoforms Critically Regulate NMDAR- and mGluR-Dependent LTD Induction.
    Authors: Yasuda Et al.
    Front Cell Neurosci  2018;12:330
  4. Presynaptic mGlu1 Receptors Control GABAB Receptors in an Antagonist-Like Manner in Mouse Cortical GABAergic and Glutamatergic Nerve Endings.
    Authors: Vergassola Et al.
    Front Mol Neurosci  2018;11:324
  5. Neural Circuit-Specialized Astrocytes: Transcriptomic, Proteomic, Morphological, and Functional Evidence.
    Authors: Chai Et al.
    Neuron  2017;95:531
  6. AKT isoforms have distinct hippocampal expression and roles in synaptic plasticity.
    Authors: Levenga Et al.
    Elife  2017;6
  7. Striatopallidal dysfunction underlies repetitive behavior in Shank3-deficient model of autism.
    Authors: Wang Et al.
    J Clin Invest  2017;127:1978
  8. 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
  9. Calmodulin activity regulates group I metabotropic glutamate receptor-mediated signal transduction and synaptic depression.
    Authors: Sethna Et al.
    J Neurosci Res  2016;94:401
  10. Selective Disruption of Metabotropic Glutamate Receptor 5-Homer Interactions Mimics Phenotypes of Fragile X Syndrome in Mice.
    Authors: Guo Et al.
    J Neurosci  2016;36:2131
  11. Application of surface plasmon resonance imaging to monitoring G protein-coupled receptor signaling and its modulation in a heterologous expression system.
    Authors: Nonobe Et al.
    BMC Biotechnol  2016;16:36
  12. 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
  13. Neuronal splicing regulator RBFOX3(NeuN) regulates adult hippocampal neurogenesis and synaptogenesis
    Authors: Lin Et al.
    PLoS One  2016;11:e0164164
  14. Dendritic spine dynamics leading to spine elimination after repeated inductions of LTD.
    Authors: Hasegawa Et al.
    J Neurosci  2015;5:7707
  15. BDNF interacts with endocannabinoids to regulate cocaine-induced synaptic plasticity in mouse midbrain DA neurons.
    Authors: Zhong Et al.
    Sci Rep  2015;35:4469
  16. 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
  17. Group I metabotropic glutamate receptor-mediated activation of PKC gamma in the nucleus accumbens core promotes the reinstatement of cocaine seeking.
    Authors: Schmidt Et al.
    Addict Biol  2015;20:285
  18. Rapid manifestation of reactive astrogliosis in acute hippocampal brain slices.
    Authors: Takano Et al.
    Glia  2014;62:78
  19. 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
  20. Long lasting protein synthesis- and activity-dependent spine shrinkage and elimination after synaptic depression.
    Authors: Ramiro-Cortés
    PLoS One  2013;8:e71155
  21. Activation of group I metabotropic glutamate receptors potentiates heteromeric kainate receptors.
    Authors: Rojas Et al.
    Mol Pharmacol  2013;83:106
  22. 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
  23. Modulation of mGluR-dependent MAP1B translation and AMPA receptor endocytosis by microRNA miR-146a-5p.
    Authors: Chen and Shen
    J Neurosci  2013;33:9013
  24. 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
  25. 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
  26. 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
  27. Synapse-specific and size-dependent mechanisms of spine structural plasticity accompanying synaptic weakening.
    Authors: Oh Et al.
    Proc Natl Acad Sci U S A  2013;110:E305
  28. A modulatory effect of the feedback from higher visual areas to V1 in the mouse.
    Authors: Pasquale and Sherman
    J Neurophysiol  2013;109:2618
  29. The analysis of purkinje cell dendritic morphology in organotypic slice cultures.
    Authors: Kapfhammer and Gugger
    J Neurosci  2012;NULL
  30. Central amygdala metabotropic glutamate receptor 5 in the modulation of visceral pain.
    Authors: Crock Et al.
    Eur J Neurosci  2012;32:14217
  31. MeCP2 phosphorylation is required for modulating synaptic scaling through mGluR5.
    Authors: Zhong Et al.
    Stem Cell Reports  2012;32:12841
  32. 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
  33. Loss of Tsc1 in vivo impairs hippocampal mGluR-LTD and increases excitatory synaptic function.
    Authors: Bateup Et al.
    Neurosci Lett  2011;31:8862
  34. 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
  35. Endocannabinoids mediate synaptic plasticity at glutamatergic synapses on spiny neurons within a basal ganglia nucleus necessary for song learning.
    Authors: Thompson and Perkel
    J Neurophysiol  2011;105:1159
  36. Activation of metabotropic glutamate receptor 5 in the amygdala modulates pain-like behavior.
    Authors: Kolber Et al.
    Sci Rep  2010;30:8203
  37. Control of cannabinoid CB1 receptor function on glutamate axon terminals by endogenous adenosine acting at A1 receptors.
    Authors: Hoffman Et al.
    J Neurosci  2010;30:545
  38. 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
  39. Calcium binding to PICK1 is essential for the intracellular retention of AMPA receptors underlying long-term depression.
    Authors: Citri Et al.
    J Neurosci  2010;30:16437
  40. Neuroligin 1 is dynamically exchanged at postsynaptic sites.
    Authors: Schapitz Et al.
    J Neurosci  2010;30:12733
  41. Activation of native TRPC3 cation channels by phospholipase D.
    Authors: Glitsch
    FASEB J  2010;24:318
  42. Converging signal on ERK1/2 activity regulates group I mGluR-mediated Arc transcription.
    Authors: Wang Et al.
    J Neurosci  2009;460:36
  43. N-MthD.-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
  44. Mobilization of calcium from intracellular stores facilitates somatodendritic DA release.
    Authors: Patel Et al.
    J Neurosci  2009;29:6568
  45. Regulated release of BDNF by cortical oligodendrocytes is mediated through metabotropic glutamate receptors and the PLC pathway.
    Authors: Bagayogo and Dreyfus
    ASN Neuro  2009;1
  46. Input-specific plasticity at excitatory synapses mediated by endocannabinoids in the dentate gyrus.
    Authors: Chiu and Castillo
    Neuropharmacology  2008;54:68
  47. Alpha1-adrenergic receptor-induced heterosynaptic long-term depression in the bed nucleus of the stria terminalis is disrupted in mouse models of affective disorders.
    Authors: McElligott
    Neuropsychopharmacology  2008;33:2313
  48. In vivo metabotropic glutamate receptor 5 (mGluR5) antagonism prevents cocaine-induced disruption of postsynaptically maintained mGluR5-dependent long-term depression.
    Authors: Grueter Et al.
    J Neurosci  2008;28:9261
  49. Fast subplasma membrane Ca2+ transients control exo-endocytosis of synaptic-like microvesicles in astrocytes.
    Authors: Marchaland Et al.
    J Neurosci  2008;28:9122
  50. The tyrosine phosphatase STEP mediates AMPA receptor endocytosis after metabotropic glutamate receptor stimulation.
    Authors: Zhang Et al.
    J Neurosci  2008;28:10561
  51. A crucial role for cAMP and protein kinase A in D1 DA receptor regulated intracellular calcium transients.
    Authors: Dai Et al.
    Neurosignals  2008;16:112
  52. Aberrant early-phase ERK inactivation impedes neuronal function in fragile X syndrome.
    Authors: Kim Et al.
    J Neurosci  2008;105:4429
  53. The different roles of cyclinD1-CDK4 in STP and mGluR-LTD during the postnatal development in mice hippocampus area CA1.
    Authors: Li Et al.
    BMC Dev Biol  2007;7:57
  54. 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
  55. Plasticity of intrinsic excitability during long-term depression is mediated through mGluR-dependent changes in I(h) in hippocampal CA1 pyramidal neurons.
    Authors: Brager and Johnston
    J Neurosci  2007;27:13926
  56. Disynaptic amplification of metabotropic glutamate receptor 1 responses in the olfactory bulb.
    Authors: Jan and Westbrook
    J Neurosci  2007;27:132
  57. Vesicular release of glutamate from unmyelinated axons in white matter.
    Authors: Ziskin Et al.
    Proc Natl Acad Sci U S A  2007;10:321
  58. AMPAR removal underlies Abeta-induced synaptic depression and dendritic spine loss.
    Authors: Hsieh Et al.
    Neuron  2006;52:831
  59. 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
  60. 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
  61. Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum.
    Authors: Rancillac Et al.
    J Neurosci  2006;26:6997
  62. Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on DArgic neurons through a microtubule-dependent mechanism.
    Authors: Jiang Et al.
    J Neurosci  2006;26:4318
  63. Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons.
    Authors: Calò Et al.
    J Neurosci  2005;25:2245
  64. 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
  65. Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling.
    Authors: Nishi Et al.
    J Neurosci  2003;100:1322
  66. 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
  67. Neutrophil-derived glutamate regulates vascular endothelial barrier function.
    Authors: Collard Et al.
    J Biol Chem  2002;277:14801
  68. Identification of sites for exponential translation in living dendrites.
    Authors: Job and Eberwine
    Proc Natl Acad Sci U S A  2001;98:13037

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mGluR antagonism with bath application
By Anonymous on 10/20/2017

Bath application on brain slice. Publication in progress.

(RS)-3,5-DHPG application in brain slice preparation
By Anonymous on 07/17/2017

(RS)-3,5-DHPG was bath applied and also pressure ejected at a concentration of up to 200 μM in a mouse brainstem slice preparation during whole-cell and perforated patch clamp. Results were consistent across different batch #s of (RS)-3,5-DHPG.

(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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