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Merck

D3689

(S)-3,5-Dihydroxyphenylglycine hydrate

≥98% (HPLC), group I metabotropic glutamate receptor agonist, powder

Synonym(s):

S-DHPG

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€341.00

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€532.10

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About This Item

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

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Product Name

(S)-3,5-Dihydroxyphenylglycine hydrate, ≥98% (HPLC), powder

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

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white

storage temp.

−20°C

Quality Level

100

Gene Information

human ... GRM1(2911)

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Sigma-Aldrich

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form

powder

form

solid

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

−20°C

storage temp.

-

storage temp.

room temp

storage temp.

2-8°C

storage condition

desiccated, protect from light

storage condition

protect from light

storage condition

desiccated, protect from light

storage condition

desiccated

color

white

color

white

color

-

color

white to beige

Application

(S)-3,5-Dihydroxyphenylglycine hydrate has been used:
  • as mGluR1/5 agonist for metabotropic glutamate receptor 1 (mGluR1/5) activation in synaptoneurosomal preparations[1]
  • in ACSF for DHPG stimulation[2]
  • to inject into basolateral amygdala to study its effect on memory expression[3]

Biochem/physiol Actions

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

Disclaimer

air sensitive

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000217656
0000217656
0000144852
0000124796
0000124797

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Overexpression of STIM1 in neurons in mouse brain improves contextual learning and impairs long-term depression
Majewski L, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1864(6), 1071-1087 (2017)
Cell-Type-Specific Translation Profiling Reveals a Novel Strategy for Treating Fragile X Syndrome
Thomson SR, et al.
Neuron, 95(3), 550-563 (2017)
Qin-Wei Wu et al.
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
Infantile amnesia reflects a developmental critical period for hippocampal learning
Travaglia A, et al.
Nature Neuroscience, 19(9), 1225-1225 (2016)
Patrick K McCamphill et al.
Science translational medicine, 12(544) (2020-05-22)
Fragile X syndrome is caused by FMR1 gene silencing and loss of the encoded fragile X mental retardation protein (FMRP), which binds to mRNA and regulates translation. Studies in the Fmr1-/y mouse model of fragile X syndrome indicate that aberrant
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