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W105

Sigma-Aldrich

S(−)-Willardiine

solid

Synonym(s):

S(−)-α-Amino--3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid

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About This Item

Empirical Formula (Hill Notation):
C7H9N3O4
CAS Number:
21416-43-3
Molecular Weight:
199.16
MDL number:
MFCD00153879
UNSPSC Code:
12352200
PubChem Substance ID:
24278009

form

solid

color

white

solubility

0.1 M NaOH: 7.2 mg/mL
DMSO: insoluble
H2O: insoluble
ethanol: insoluble

SMILES string

[H]C1=CN(C[C@H](N)C(O)=O)C(=O)NC1=O

Gene Information

human ... GRIA1(2890) , GRIA2(2891) , GRIA3(2892) , GRIA4(2893) , GRIK1(2897) , GRIK2(2898) , GRIK3(2899) , GRIK4(2900) , GRIK5(2901)

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Biochem/physiol Actions

AMPA/kainate glutamate receptor agonist.

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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N K Thomas et al.
Neuropharmacology, 37(10-11), 1223-1237 (1998-12-16)
The objectives of this study, conducted on neonatal rat spinal cord and dorsal roots in vitro, were to characterise the actions of a range of willardiine analogues on GluR5-containing kainate receptors present in dorsal roots, to determine whether GluR5-containing receptors
Swarna Ramaswamy et al.
The Journal of biological chemistry, 287(52), 43557-43564 (2012-11-02)
We have investigated the range of cleft closure conformational states that the agonist-binding domains of the α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptors occupy when bound to a series of willardiine derivatives using single-molecule FRET. These studies show that the agonist-binding domain exhibits
Nigel P Dolman et al.
Journal of medicinal chemistry, 50(7), 1558-1570 (2007-03-14)
Some N3-substituted analogues of willardiine such as 11 and 13 are selective kainate receptor antagonists. In an attempt to improve the potency and selectivity for kainate receptors, a range of analogues of 11 and 13 were synthesized with 5-substituents on
Kimberly A Mankiewicz et al.
Biochemistry, 47(1), 398-404 (2007-12-18)
Alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors, one subtype in the family of ionotropic glutamate receptors, are the main receptors responsible for excitatory signaling in the mammalian central nervous system. Previous studies utilitizing the isolated ligand binding domain of these receptors have provided
C F Zorumski et al.
Molecular pharmacology, 40(1), 45-51 (1991-07-01)
The physiology and pharmacology of willardiine and bromowillardiine, structural analogues of quisqualate, were studied in cultured postnatal rat hippocampal neurons using whole-cell voltage-clamp techniques. These agonists appear to act at a shared non-N-methyl-D-aspartate (non-NMDA) receptor-channel complex and gate nonselective cationic
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