(S)-3,5-DHPG is a modest but selective agonist of group I metabotropic glutamate receptors (mGluRs) with Kis of 0.9 µM for mGluR1a and 3.9 µM for mGluR5a. (S)-3,5-DHPG displays anxiolytic (anti-anxiety) activity in hypoxic rats.

Physicochemical Properties

Molecular Formula	C8H11NO5
Molecular Weight	201.17
Exact Mass	183.053
CAS #	162870-29-3
Related CAS #	DHPG;146255-66-5
PubChem CID	443586
Appearance	White to off-white solid powder
Density	1.5±0.1 g/cm3
Boiling Point	448.8±33.0 °C at 760 mmHg
Flash Point	225.2±25.4 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.680
LogP	-0.52
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Heavy Atom Count	13
Complexity	187
Defined Atom Stereocenter Count	1
SMILES	C1=C(C=C(C=C1O)O)[C@@H](C(=O)O)N
InChi Key	HOOWCUZPEFNHDT-ZETCQYMHSA-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)/t7-/m0/s1
Chemical Name	(2S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid
Synonyms	Dihydroxyphenylglycine DHPG J516.528H
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
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	(S)-3,5-DHPG displaces the putative group I mGlu binding site, the high-affinity squilinic acid site, specifically [1].
ln Vivo	(S)-3,5-DHPG (icv; 0.01, 0.1, and 1.0 nmol/5 μL) shows anti-anxiety effect and enhances consolidation and recovery in male Wistar hypoxic rats weighing 160–180 g[2].
References	[1]. Characterization of [(3)H]Quisqualate Binding to Recombinant Rat Metabotropic Glutamate 1a and 5a Receptors and to Rat and Human Brain Sections. J Neurochem. 2000 Dec;75(6):2590-601. [2]. Effect of (S)-3,5-DHPG on Learning, Exploratory Activity and Anxiety in Rats With Experimental Hypoxia. Pol J Pharmacol. Jan-Feb 2002;54(1):11-8.
Additional Infomation	(S)-3,5-dihydroxyphenylglycine is a glycine derivative that is L-alpha-phenylglycine substituted at positions 3 and 5 on the phenyl ring by hydroxy groups. It is a member of resorcinols and a non-proteinogenic L-alpha-amino acid. It is functionally related to a L-alpha-phenylglycine. It is a tautomer of a (S)-3,5-dihydroxyphenylglycine zwitterion.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~545.97 mM) H2O : ~25 mg/mL (~136.49 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.65 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 25.0 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 3: ≥ 2.5 mg/mL (13.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.9709 mL	24.8546 mL	49.7092 mL
	5 mM	0.9942 mL	4.9709 mL	9.9418 mL
	10 mM	0.4971 mL	2.4855 mL	4.9709 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.