DHPG ((RS)-3,5-DHPG) is an amino acid (AA) that is a potent and specific agonist of the first group of metabotropic glutamate receptors mGluR (mGluR 1 and mGluR 5). Group mGluR had no obvious effect. DHPG ((RS)-3,5-DHPG) is also a potent antagonist of mGluRs coupled to phospholipase D.

Physicochemical Properties

Molecular Formula	C8H9NO4
Molecular Weight	183.161362409592
Exact Mass	183.053
CAS #	146255-66-5
Related CAS #	(S)-3,5-DHPG;162870-29-3
PubChem CID	108001
Appearance	Off-white to gray solid powder
Density	1.55g/cm3
Boiling Point	448.8ºC at 760mmHg
Flash Point	225.2ºC
LogP	0.882
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Heavy Atom Count	13
Complexity	187
Defined Atom Stereocenter Count	0
InChi Key	HOOWCUZPEFNHDT-UHFFFAOYSA-N
InChi Code	InChI=1S/C8H9NO4/c9-7(8(12)13)4-1-5(10)3-6(11)2-4/h1-3,7,10-11H,9H2,(H,12,13)
Chemical Name	2-amino-2-(3,5-dihydroxyphenyl)acetic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In adult rat hippocampal slices, DHPG (100 μM) had no detectable effect on isoproterenol (Iso, 10 μM)-stimulated cAMP accumulation, in contrast to the robust potentiation observed with the mGluR agonist 1S,3R-ACPD. [1] This lack of effect on cAMP potentiation, combined with its known activity on phosphoinositide hydrolysis, was used as key pharmacological evidence to argue that mGluR-mediated potentiation of cAMP responses is not secondary to phosphoinositide hydrolysis and is likely mediated by a group II-like mGluR. [1] In adult rat hippocampal slices, DHPG (100 μM) promotes the formation of [³H]-inositol phosphates ([³H]-IPs), although it produces only about half the maximal response of 100 μM (1S,3R)-ACPD.[2] When tested on phospholipase D (PLD) activity in hippocampal slices, DHPG (up to 1 mM) is virtually inactive as an agonist.[2] However, DHPG (100 and 300 μM) inhibits the formation of [³H]-phosphatidylethanol ([³H]-PEt) induced by 100 μM (1S,3R)-ACPD in a concentration-dependent manner.[2]
References	[1]. Metabotropic glutamate receptor (mGluR)-mediated potentiation of cyclic AMP responses does not require phosphoinositide hydrolysis: mediation by a group II-like mGluR. J Neurochem. 1995 Feb;64(2):592-9. [2]. Pharmacological characterization of metabotropic glutamate receptors coupled to phospholipase D in the rat hippocampus. Br J Pharmacol. 1996 Jun;118(4):1035-43.
Additional Infomation	2-amino-2-(3,5-dihydroxyphenyl)acetic acid is an alpha-amino acid. (RS)-3,5-Dihydroxyphenylglycine (DHPG) is used as a selective pharmacological tool to activate group I mGluRs. Based on data from transfected cells cited in the literature, the EC50 of DHPG for mGluR1 is approximately 60 μM. [1] Its pharmacological profile (active on PI hydrolysis but inactive on cAMP potentiation in the assay system used) helped dissect the signaling pathways coupled to different mGluR subtypes. [1] DHPG is referred to as a recently characterized selective agonist of mGluRs of the first group, which are coupled to phosphoinositide hydrolysis.[2] The study demonstrates that while DHPG stimulates the phospholipase C (PLC) pathway, it does not stimulate the phospholipase D (PLD) pathway and can even inhibit PLD activity induced by (1S,3R)-ACPD, suggesting independent coupling of mGluRs to PLC and PLD pathways.[2]

Solubility Data

Solubility (In Vitro)

DMSO : ~5 mg/mL (~27.30 mM) H2O : ~1 mg/mL (~5.46 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 0.5 mg/mL (2.73 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: 4.55 mg/mL (24.84 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.4597 mL	27.2985 mL	54.5971 mL
	5 mM	1.0919 mL	5.4597 mL	10.9194 mL
	10 mM	0.5460 mL	2.7299 mL	5.4597 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.