An internal standard for the quantification of cinnabarinic acid
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Unlabeled Version(s)
11988Cinnabarinic Acid
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Cinnabarinic Acid-d4

Item No. 37209

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-3-oxo-3H-phenoxazine-4,6,7,8-d4-1,9-dicarboxylic acid
Molecular Formula
C14H4D4N2O6
Formula Weight
304.3
Purity
≥99% deuterated forms (d1-d4)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O=C(C(C([2H])=C([2H])C([2H])=C1OC2=C3[2H])=C1N=C2C(C(O)=O)=C(N)C3=O)O
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)/i1D,2D,3D,4D
InChi Key
FSBKJYLVDRVPTK-RHQRLBAQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $106

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    5 mg

    $475

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    10 mg

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    Product Description

    Cinnabarinic acid-d4 is intended for use as an internal standard for the quantification of cinnabarinic acid (Item No. 11988) by GC- or LC-MS. 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).