An agonist of mGluR4 and active metabolite of 3-hydroxyanthranilic acid
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Labeled Version(s)
37209Cinnabarinic Acid-d4
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Cinnabarinic Acid

Item No. 11988

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
CAS Number
606-59-7
Molecular Formula
C14H8N2O6
Formula Weight
300.3
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mM (warmed)
λmax
234, 426, 448 nm
SMILES
O=C1C(N)=C(C(O)=O)C2=NC3=C(C=CC=C3C(O)=O)OC2=C1
InChi Code
InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)
InChi Key
FSBKJYLVDRVPTK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $148

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    50 mg

    $657

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    Product Description

    Cinnabarinic acid is an agonist of metabotropic glutamate receptor 4 (mGluR4) and active metabolite of 3-hydroxyanthranilic acid.1,2 It is formed via two-step oxidation of 3-hydroxyanthranilic acid. Cinnabarinic acid (100 µM) selectively induces inositol phosphate production in HEK293 cells expressing mGluR4 over HEK293 cells expressing mGluR1, mGluR2, mGluR5, mGluR6, mGluR7, or mGluR8.1 It inhibits D-amino acid oxidase (DAAO) in a cell-free assay (IC50 = 1.37 µM).3 Cinnabarinic acid (30 µM) increases levels of reactive oxygen species (ROS) and induces apoptosis in primary mouse thymocytes.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fazio, F., Lionetto, L., Molinaro, G., et al. Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors. Mol. Pharmacol. 81(5), 643-656 (2012).

    2. Subba Rao, P.V., and Vaidyanathan, C.S. Enzymic conversion of 3-hydroxyanthranilic acid into cinnabarinic acid. Partial purification and properties of rat-liver cinnabarinate synthase. Biochem. J. 99(2), 317-322 (1966).

    3. Lefin, R., Petzer, A., Cloete, S.J., et al. Phenothiazine, anthraquinone and related tricyclic derivatives as inhibitors of ᴅ-amino acid oxidase. Results Chem. 4, 100278 (2022).

    4. Hiramatsu, R., Hara, T., Akimoto, H., et al. Cinnabarinic acid generated from 3-hydroxyanthranilic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase. J. Cell. Biochem. 103(1), 42-53 (2008).