CAS 74936-72-4 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (HCID 173322)

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Basic information

CAS: 74936-72-4
Standard SMILES: COC(=O)C1=C(C)NC(C)=C(C(=O)O)C1c1cccc([N+](=O)[O-])c1
InChIKey: JPXPPUOCSLMCHK-UHFFFAOYSA-N
Molecular formula: C16H16N2O6
Average molar mass: 332.31 g/mol
Monoisotopic mass: 332.10083623

Names & identifiers

Preferred name: 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester
IUPAC: 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
English name: 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
Molecular formula: C16H16N2O6
Molecular weight: 332.31

Names & synonyms

74936-72-4Carboxy-nifedipine5DU0E310OI1,4-Dihydro-2,6-dimethyl-4--(3-nitrophenyl)pyridine-3-carboxylic acid-5-carboxylic methyl ester2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterRefChem:8177815-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl EsterMFCD00475478Methyl hydrogen 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateC16H16N2O6

Show more names

DHP-050PRAN-001278-034-2Le Chi Chi1,4-DHPCOOHUNII:5DU0E310OINicardipine USP RC ANifedipine Impurity 2Le Chi mother nucleusLercanidipine nucleus

1,4-DIHYDRO-5-METHOXYCARBONYL-2,6-DIMETHYL-4-(3-NITROPHENYL)PYRIDINE-3-CARBOXYLIC ACID1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester2,6-DIMETHYL-5-METHOXYCARBONYL-4-(3-NITROPHENYL)-1,4-DIHYDROPYRIDINE-3-CARBOXYLIC ACIDMonomethyl 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylateNicardipine USP Related Compound AUNII-5DU0E310OI1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic Acid Methyl EsterEINECS 278-034-2

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 121 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 7
Rotatable bonds: 4
Heavy atoms: 24
Formal charge: 0
Complexity: 631

Physicochemical properties

Melting point: 200 · 200-202C
Boiling point: 505 · 505.0±50.0 °C(Predicted)
Density: 1.345 · 1.345±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Sparingly), Methanol (Slightly, Heated)
pka: 1.66 · 1.66±0.70(Predicted)
form: Solid
color: Pale Yellow to Light Yellow
InChI: InChI=1S/C16H16N2O6/c1-8-12(15(19)20)14(13(9(2)17-8)16(21)24-3)10-5-4-6-11(7-10)18(22)23/h4-7,14,17H,1-3H3,(H,19,20)
InChIKey: JPXPPUOCSLMCHK-UHFFFAOYSA-N
SMILES: C1(C)NC(C)=C(C(O)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OC)=O
FDA UNII: 5 DU0E310OI · 5DU0E310OI
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.

Warning

H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 1 of 4 reports by companies.；There are 2 notifications provided by 3 of 4 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationStatus: Active Update: 25-09-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/16483

Hazard Classes and CategoriesAcute Tox. 4 (75%)

Regulatory information

Regulatory InformationStatus: Active Update: 25-09-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/16483

Safety data

hs_code: 2934999090
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
REACH Registrations: Active

Chemistry & industry

Pharmacology

Metabolism/Metabolites5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid is a known human metabolite of Pranidipine and barnidipine.

Applications · 3 items

Description5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid(1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester) is a pharmaceutical intermediate ingredient used in the preparation of Barnidipine, Lercanidipine hydrochloride and nitrendipine analogues. These drugs are all calcium channel blockers and are used to treat various forms of hypertension.

Uses1,4-Dihydropyridine derivative used in the prevention and therapy of atherosclerotic degradation of arterial walls. Nicardipine USP Related Compound A.

Uses1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester can be used in the prevention and therapy of atherosclerotic degradation of arterial walls.