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D3689

Sigma-Aldrich

(S)-3,5-Dihydroxyphenylglycine hydrate

≥98% (HPLC), powder

Synonym(s):

S-DHPG

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About This Item

Empirical Formula (Hill Notation):
C8H9NO4 · xH2O
CAS Number:
162870-29-3
Molecular Weight:
183.16 (anhydrous basis)
MDL number:
MFCD11044457
UNSPSC Code:
12352209
PubChem Substance ID:
24278366
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white

storage temp.

−20°C

SMILES string

O.N[C@H](C(O)=O)c1cc(O)cc(O)c1

InChI

1S/C8H9NO4.H2O/c9-7(8(12)13)4-1-5(10)3-6(11)2-4;/h1-3,7,10-11H,9H2,(H,12,13);1H2/t7-;/m0./s1

InChI key

QZEFIWWBQUKNFA-FJXQXJEOSA-N

Gene Information

human ... GRM1(2911)

Application

(S)-3,5-Dihydroxyphenylglycine hydrate has been used:
  • as mGluR1/5 agonist for metabotropic glutamate receptor 1 (mGluR1/5) activation in synaptoneurosomal preparations
  • in ACSF for DHPG stimulation
  • to inject into basolateral amygdala to study its effect on memory expression

Biochem/physiol Actions

(S)-3,5-Dihydroxyphenylglycine hydrate is a group I metabotropic glutamate receptor agonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (G Protein Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

air sensitive

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Infantile amnesia reflects a developmental critical period for hippocampal learning
Travaglia A, et al.
Nature Neuroscience, 19(9), 1225-1225 (2016)
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Frontiers in cell and developmental biology, 8, 569889-569889 (2021-02-09)
Spinocerebellar ataxias (SCAs) are a group of hereditary neurodegenerative diseases which are caused by diverse genetic mutations in a variety of different genes. We have identified RGS8, a regulator of G-protein signaling, as one of the genes which are dysregulated
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The hypothalamic paraventricular nucleus (PVN) plays a major role in generating increased sympathetic output in hypertension. Although group III metabotropic glutamate receptors (mGluRs) are expressed in the hypothalamus, little is known about their contribution to regulating PVN presympathetic neurons in
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