7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrile

• ChemBase ID: 92961
• Molecular Formular: C9H4N4O4
• Molecular Mass: 232.15246
• Monoisotopic Mass: 232.02325463
• SMILES: [nH]1c2c(cc(c(c2)C#N)[N+](=O)[O-])[nH]c(=O)c1=O
• Canonical SMILES: N#Cc1cc2[nH]c(=O)c(=O)[nH]c2cc1[N+](=O)[O-]
• InChI: InChI=1S/C9H4N4O4/c10-3-4-1-5-6(2-7(4)13(16)17)12-9(15)8(14)11-5/h1-2H,(H,11,14)(H,12,15)
• InChIKey: RPXVIAFEQBNEAX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carbonitrile
• IUPAC Traditional name: CNQX
• Synonyms: 6-Cyano-7-nitroquinoxaline-2,3-dione; 1,2,3,4-Tetrahydro-7-nitro-2,3-dioxo-6-quinoxalinecarbonitrile; 6-Cyano-2,3-dihydroxy-7-nitroquinoxaline; 6-Cyano-7-nitroquinoxaline-2,3-dione; FG-9065; CNQX; CNQX

Database IDs

• CAS Number: 115066-14-3
• MDL Number: MFCD00069232
• PubChem SID: 162079659; 24892392
• PubChem CID: 3721046

CALCULATED PROPERTIES

• Acid pKa: 9.868097
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.4276691
• LogD (pH = 7.4): 0.42628488
• Log P: 0.42768678
• Molar Refractivity: 57.9815 cm^3
• Polarizability: 19.62026 Å^3
• Polar Surface Area: 127.81 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dilute Aqueous Base; DMSO; DMSO: >10 mg/mL; H2O: insoluble
• Apperance: Pale Yellow Solid; yellow solid
• Melting Point: >300°C

Safety Information

• Storage Condition: protect from light; Refrigerator; Room Temperature (15-30°C), Protect from light
• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409)

Product Information

• Purity: ≥98%; ≥98% (HPLC)

DETAILS

MP Biomedicals - 02159761

Purity: >98%
Potent, competitive and selective kainate/quisqualate (non-NMDA) receptor antagonist.

Apollo Scientific Ltd - OR9820T

A potent, competitive non-NMDA (kainate/quisqualate) receptor antagonist.

Sigma Aldrich - C127

Biochem/physiol Actions
Potent, competitive AMPA/kainate glutamate receptor antagonist.

Toronto Research Chemicals - C982000

A potent, competitive kainate/quisqualate (non-NMDA) receptor antagonist. IC50 of tritiated ligands to rat cortical membranes by CNQX: AMPA, Kainate and CPP are 0.3mM, 1.5mM, and 25mM, respectively.

REFERENCES

• Honore, et al. Science, 241, 701 (1988)
• Haas, H.S., et al.: Int. J. Oncol., 27, 867 (1988)
• Kobayashi, K., et al.: J. Pharmacol. Sci., 108, 517 (1988)
• Shabat-Simon, M., et al.: J. Neurosci., 28, 8406 (1988)
• Cruz, L.A., et al.: J. Med. Chem., 51, 5856 (