3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate

• ChemBase ID: 154218
• Molecular Formular: C17H16N2O6
• Molecular Mass: 344.31874
• Monoisotopic Mass: 344.10083624
• SMILES: Cc1c(c(c(c(n1)C)C(=O)OC)c1ccccc1[N+](=O)[O-])C(=O)OC
• Canonical SMILES: COC(=O)c1c(C)nc(c(c1c1ccccc1[N+](=O)[O-])C(=O)OC)C
• InChI: InChI=1S/C17H16N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8H,1-4H3
• InChIKey: UMQHJQGNGLQJPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
• IUPAC Traditional name: 3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
• Synonyms: 2,6-Dimethyl-4-(2′-nitrophenyl)-3,5-pyridinecarboxylic acid dimethyl ester; Oxidized Nifedipine; 2,6-Dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3,5-Dimethyl Ester; Dimethyl 2,6-Dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate; B 4759; Dehydro Nifedipine

Database IDs

• CAS Number: 67035-22-7
• MDL Number: MFCD00153847
• PubChem SID: 162248357
• PubChem CID: 128753

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.606124
• LogD (pH = 7.4): 2.6123967
• Log P: 2.6124773
• Molar Refractivity: 89.5956 cm^3
• Polarizability: 34.669144 Å^3
• Polar Surface Area: 111.31 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid; yellow powder
• Melting Point: 100-105 °C; 102-105°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (HPLC)
• Empirical Formula (Hill Notation): C17H16N2O6

DETAILS

Sigma Aldrich - UC167

Biochem/physiol Actions
CYP3A4 nifedipine metabolite. Nifedipine (parent compound) is an antianginal and antihypertensive agent.

Toronto Research Chemicals - D229800

The main Nifedipine metabolite in human plasma.

REFERENCES

• Guengerich, F., et al.: J. Biol. Chem., 261, 5051 (1986)
• Bork, R., et al.: J. Biol. Chem., 264, 910 (1986)
• Kerla, V., et al.: Biochem. Pharmacol., 44, 1745 (1986)