(RS)-3,5-DHPG

Cat. No. 0342

(RS)-3,5-DHPG C8H9NO4 [19641-83-9]

Price and Availability

For (RS)-3,5-DHPG pricing & availability please select your country from the drop down menu:
Submit
By clicking submit you agree to accept a cookie from Tocris Bioscience. For details, please read our privacy and cookie policy.

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

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
Select another batch:

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.

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.

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.

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

If you know of a relevant reference for this product please let us know.

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

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.

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.

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

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.

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.

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

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.

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.

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.

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.

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

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.

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

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.

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.

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

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

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.

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

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

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

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

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

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.

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.

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.

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. 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.show all ▼show less ▲

View Related Products by Target

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

Quick Order

Find multiple products by catalog number

divider line

Pain Research Product Guide

Pain Research Product Guide

Our Pain guide highlights over 280 products for Pain research. Request copy or view PDF today.

divider line

GPCR Product Listing

GPCR Product Listing

Highlights over 450 products for GPCRs. Request copy or view PDF today.

divider line

mGlu Receptors Review

Written by Francine Acher

Metabotropic Glutamate Receptors Scientific Review

Our Metabotropic Glutamate Receptor review gives an overview of the pharmacological ligands used to study the mGlu receptors . Request copy or view PDF today.

divider line

Peripheral Sensitization

Written by Grant D. Nicol and Michael R. Vasko

Pain Life Science Poster

Our Peripheral Sensitization poster gives a summary of the excitatory and inhibitory signaling pathways involved in modulation of peripheral sensitization. Request copy or view PDF today.

divider line

Parkinson's disease: Neurobiology and Therapeutic Strategies

Written by Anthony H.V. Schapira

Parkinson's Life Science Poster

Our Parkinson's disease (PD) poster summarizes the neurobiology of the disease, and highlights current therapeutic treatments for symptomatic PD. Request copy or view PDF today.

divider line

Antidepressants - Current and Future Targets

Written by P. Skolnich et al

Depression Life Science Poster

Our Depression poster highlights presynaptic and postsynaptic targets for the potential treatment of major depressive disorder. Request copy or view PDF today.

divider line

Learning and Memory

Written by Clea Warburton and Zafar Bashir

Learning & Memory Life Science Poster

Our Learning and Memory poster gives an overview of the cellular mechanisms underlying recognition memory and its links to long-term depression. Request copy or view PDF today.

divider line

Mechanisms of Addiction

Addiction Life Science Poster

Written by Prof David Nutt, this poster summarizes the brain circuits and neurotransmitter systems that are affected by the main classes of addictive drugs. Request copy or view PDF today.

divider line

Huntington's Disease: Pathophysiology and Clinical Prospects

Huntington's Disease Life Science Poster

Our Huntington's Disease (HD) poster summarizes the medium spiny neuron intracellular signaling pathways implicated in the pathology of HD. Request copy or view PDF today.

divider line

New Products in this Area

(±)-ADX 71743

Negative allosteric modulator at mGlu7; brain penetrant

VU 0409551

Selective mGlu5 positive allosteric modulator; brain penetrant and orally bioavailable

Sign-up for new product e-alerts
divider line

Bio-Techne Events

Pharmacology 2016

Pharmacology 2016

December 13 - 15, 2016

London, UK

Booth: 7