(RS)-3,5-DHPG

Pricing Availability Delivery Time Qty
Cat.No. 0342 - (RS)-3,5-DHPG | C8H9NO4 | CAS No. 19641-83-9
Description: Selective group I mGlu agonist
Chemical Name: (RS)-3,5-Dihydroxyphenylglycine
Purity: ≥99% (HPLC)
Datasheet
Citations (39)
Literature

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)-3,5-DHPG (Cat. No. 0805) also available.

Technical Data

M. Wt 183.16
Formula C8H9NO4
Storage Desiccate at -20°C
Purity ≥99% (HPLC)
CAS Number 19641-83-9
PubChem ID 108001
InChI Key HOOWCUZPEFNHDT-UHFFFAOYSA-N
Smiles NC(C(O)=O)C1=CC(O)=CC(O)=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
phosphate buffered saline 1.83 10
1eq. HCl 18.32 100
1eq. NaOH 18.32 100
water 1.83 10

Preparing Stock Solutions

The following data is based on the product molecular weight 183.16. 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 5.46 mL 27.3 mL 54.6 mL
5 mM 1.09 mL 5.46 mL 10.92 mL
10 mM 0.55 mL 2.73 mL 5.46 mL
50 mM 0.11 mL 0.55 mL 1.09 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:
Safety Datasheet

References

References are publications that support the products' biological activity.

Ito et al (1992) 3,5-Dihydroxyphenylglycine: a potent agonist of metabotropic glutamate receptors. NeuroReport 3 1013 PMID: 1362358

Mistry et al (1998) Regulation of phosphoinositide turnover in neonatal rat cerebral cortex by group I- and II-selective metabotropic glutamate receptor agonists. Br.J.Pharmacol. 123 581 PMID: 9504400

Pellegrini-Giampietro et al (1996) Pharmacological characterization of metabotropic glutamate recpetors coupled to phopholipase D in the rat hippocampus. Br.J.Pharmacol. 118 1035 PMID: 8799579

Palmer et al (1997) The group I mGlu receptor agonist DHPG induces a novel form of LTD in the CA1 region of the hippocampus. Neuropharmacology 36 1517 PMID: 9517422


If you know of a relevant reference for (RS)-3,5-DHPG, please let us know.

View Related Products by Product Action

View all Glutamate (Metabotropic) Group I Receptor Agonists

Keywords: (RS)-3,5-DHPG, supplier, Selective, group, I, mGlur, agonists, Group, Receptors, mGlu1, mGlu5, mGluR1, mGluR5, Glutamate, Metabotropic, Glutamate, (Metabotropic), Group, I, Receptors, Glutamate, (Metabotropic), Group, I, Receptors, Tocris Bioscience

39 Citations for (RS)-3,5-DHPG

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

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

Lin et al (2016) Neuronal splicing regulator RBFOX3(NeuN) regulates adult hippocampal neurogenesis and synaptogenesis PLoS One 11 e0164164 PMID: 27701470

Romei et al (2016) Colocalization of neurotransmitter transporters on the plasma membrane of the same nerve terminal may reflect cotransmission. Brain Research Bulletin 127 100 PMID: 27565422

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

Hasegawa et al (2015) Dendritic spine dynamics leading to spine elimination after repeated inductions of LTD. J Neurosci 5 7707 PMID: 25573377

Choi et al (2015) PDE-4 inhibition rescues aberrant synaptic plasticity in Drosophila and mouse models of fragile X syndrome. Proc Natl Acad Sci U S A 35 396 PMID: 25568131

Takano et al (2014) Rapid manifestation of reactive astrogliosis in acute hippocampal brain slices. Glia 62 78 PMID: 24272704

Lee et al (2014) Long-term depression-inducing stimuli promote cleavage of the synaptic adhesion molecule NGL-3 through NMDA receptors, matrix metalloproteinases and presenilin/γ-secretase. Philos Trans R Soc Lond B Biol Sci 369 20130158 PMID: 24298159

Iliff et al (2013) Impaired activity-dependent FMRP translation and enhanced mGluR-dependent LTD in Fragile X premutation mice. Hum Mol Genet 22 1180 PMID: 23250915

Chen and Shen (2013) Modulation of mGluR-dependent MAP1B translation and AMPA receptor endocytosis by microRNA miR-146a-5p. J Neurosci 33 9013 PMID: 23699512

Xu et al (2013) Simultaneous monitoring of presynaptic transmitter release and postsynaptic receptor trafficking reveals an enhancement of presynaptic activity in metabotropic glutamate receptor-mediated long-term depression. J Neurosci 33 5867 PMID: 23536098

Sakuragi et al (2013) Involvement of TrkB- and p75(NTR)-signaling pathways in two contrasting forms of long-lasting synaptic plasticity. J Vis Exp 3 3185 PMID: 24212565

Sherkhane and Kapfhammer (2013) The plasma membrane Ca2+-ATPase2 (PMCA2) is involved in the regulation of Purkinje cell dendritic growth in cerebellar organotypic slice cultures. J Neurosci 2013 321685 PMID: 24288624

Kapfhammer and Gugger (2012) The analysis of purkinje cell dendritic morphology in organotypic slice cultures. J Neurosci NULL PMID: 22473312

Zhong et al (2012) MeCP2 phosphorylation is required for modulating synaptic scaling through mGluR5. Stem Cell Reports 32 12841 PMID: 22973007

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

Coulon et al (2011) Activity Modes in Thalamocortical Relay Neurons are Modulated by G(q)/G(11) Family G-proteins - Serotonergic and Glutamatergic Signaling. Front Cell Neurosci 4 132 PMID: 21267426

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

Bateup et al (2011) Loss of Tsc1 in vivo impairs hippocampal mGluR-LTD and increases excitatory synaptic function. Neurosci Lett 31 8862 PMID: 21677170

Kim et al (2010) Group II metabotropic glutamate receptor stimulation triggers production and release of Alzheimer's amyloid(β)42 from isolated intact nerve terminals. J Neurosci 30 3870 PMID: 20237257

Schapitz et al (2010) Neuroligin 1 is dynamically exchanged at postsynaptic sites. J Neurosci 30 12733 PMID: 20861378

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

Wang et al (2009) Converging signal on ERK1/2 activity regulates group I mGluR-mediated Arc transcription. J Neurosci 460 36 PMID: 19446601

Citri et al (2009) N-methyl-D-aspartate receptor- and metabotropic glutamate receptor-dependent long-term depression are differentially regulated by the ubiquitin-proteasome system. J Neurosci 30 1443 PMID: 19821836

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

Marchaland et al (2008) Fast subplasma membrane Ca2+ transients control exo-endocytosis of synaptic-like microvesicles in astrocytes. J Neurosci 28 9122 PMID: 18784293

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

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

Jan and Westbrook (2007) Disynaptic amplification of metabotropic glutamate receptor 1 responses in the olfactory bulb. J Neurosci 27 132 PMID: 17202480

Ziskin et al (2007) Vesicular release of glutamate from unmyelinated axons in white matter. Proc Natl Acad Sci U S A 10 321 PMID: 17293857

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

Etkin et al (2006) A role in learning for SRF: deletion in the adult forebrain disrupts LTD and the formation of an immediate memory of a novel context. Neuron 50 127 PMID: 16600861

Rancillac et al (2006) Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum. J Neurosci 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

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

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

Collard et al (2002) Neutrophil-derived glutamate regulates vascular endothelial barrier function. J Biol Chem 277 14801 PMID: 11847215

Huber et al (2002) Altered synaptic plasticity in a mouse model of fragile X mental retardation. Proc Natl Acad Sci U S A 99 7746 PMID: 12032354

Job and Eberwine (2001) Identification of sites for exponential translation in living dendrites. Proc Natl Acad Sci U S A 98 13037 PMID: 11606784


Do you know of a great paper that uses (RS)-3,5-DHPG from Tocris? If so please let us know.

Commented out for usability testing

Reviews

TODO: Add Reviews

Literature in this Area

GPCR

GPCR Product Listing

A collection of over 450 products for G protein-coupled receptors, the listing includes research tools for the study of:

  • Rhodopsin-like Receptors
  • Secretin-like Receptors
  • Glutamate Receptors
  • Frizzled Receptors
  • GPCR Signaling
Pain

Pain Research Product Guide

A collection of over 250 products for pain research, the guide includes research tools for the study of:

  • Nociception
  • Ion Channels
  • G-Protein-Coupled Receptors
  • Intracellular Signaling
Metabotropic Glutamate Receptors

Metabotropic Glutamate Receptors Scientific Review

Written by Francine Acher, this review discusses the pharmacology and therapeutic potential of mGlu receptors, and the compounds acting upon them; compounds available from Tocris are listed.

Addiction

Addiction Poster

The key feature of drug addiction is the inability to stop using a drug despite clear evidence of harm. This poster describes the brain circuits associated with addiction, and provides an overview of the main classes of addictive drugs and the neurotransmitter systems that they target.

Depression

Depression Poster

Major depressive disorder is characterized by depressed mood and a loss of interest and/or pleasure. Updated in 2015 this poster highlights presynaptic and postsynaptic targets for the potential treatment of major depressive disorder, as well as outlining the pharmacology of currently approved antidepressant drugs.

Huntington's Disease

Huntington's Disease Poster

Huntington's disease (HD) is a monogenic neurodegenerative disorder, which is characterized by the prevalent loss of GABAergic medium spiny neurons (MSN) in the striatum. This poster summarizes the MSN intracellular signaling pathways implicated in the pathology of HD, as well as highlighting the use of iPSCs for HD modeling.

Learning & Memory

Learning & Memory Poster

Recognition memory enables us to make judgements about whether or not we have encountered a particular stimulus before. This poster outlines the cellular mechanisms underlying recognition memory and its links to long-term depression, as well as the use of pharmacological intervention to assess the role of neurotransmitters in recognition memory.

Pain

Pain Poster

Peripheral sensitization is the reduction in the threshold of excitability of sensory neurons that results in an augmented response to a given external stimulus. This poster outlines the excitatory and inhibitory signaling pathways involved in modulation of peripheral sensitization. The role of ion channels, GPCRs, neurotrophins, and cytokines in sensory neurons are also described.

Parkinson's

Parkinson's Poster

Parkinson's disease (PD) causes chronic disability and is the second most common neurodegenerative condition. This poster outlines the neurobiology of the disease, as well as highlighting current therapeutic treatments for symptomatic PD, and emerging therapeutic strategies to delay PD onset and progression.

Pathways for (RS)-3,5-DHPG

Protocols

TODO: Add Protocols