3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

• ChemBase ID: 105444
• Molecular Formular: C26H30ClN3O6
• Molecular Mass: 515.9859
• Monoisotopic Mass: 515.18231338
• SMILES: Cl.COC(=O)C1=C(C)NC(=C(C1c1cc(ccc1)[N+](=O)[O-])C(=O)OCCN(C)Cc1ccccc1)C
• Canonical SMILES: COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OCCN(Cc1ccccc1)C)C.Cl
• InChI: InChI=1S/C26H29N3O6.ClH/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19;/h5-12,15,24,27H,13-14,16H2,1-4H3;1H
• InChIKey: AIKVCUNQWYTVTO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• IUPAC Traditional name: nicardipine hydrochloride
• Synonyms: Nicardipine HCl; 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 2-[Methyl(phenylmethyl)amino]ethyl Ester Hydrochloride; RS-69216; Antagonyl; Barizin; Bionicard; Cardene; Dacarel; Vasonase; 1,4-Dihydro-2,6-dimethyl-4-[3-nitrophenyl]methyl-2-[methyl-(phenyl-methl)amino]-3,5-pyridinedicarboxylic acid ethyl ester; NICARDIPINE HYDROCHLORIDE; 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)methyl-2-[methyl(phenylmethyl)amino]-3,5-pyridinedicarboxylic acid ethyl ester hydrochloride; YC-93; Nicardipine hydrochloride; 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

Database IDs

• CAS Number: 54527-84-3
• EC Number: 259-198-4
• MDL Number: MFCD00057327
• PubChem SID: 24277856; 162092407
• PubChem CID: 41114

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.9389367
• LogD (pH = 7.4): 2.7129548
• Log P: 3.5586119
• Molar Refractivity: 133.7922 cm^3
• Polarizability: 50.553032 Å^3
• Polar Surface Area: 111.01 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false
• Acid pKa: 19.468227

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: insoluble; Chloroform; DMSO: ~1 mg/mL; H2O: slightly soluble; methanol: soluble
• Apperance: yellow powder; Yellow Solid
• Melting Point: 176-178°C
• Hydrophobicity(logP): 5.512

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• RTECS: US7972100
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 23/24/25; R:25
• Safety Statements: 36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98%; 95%
• Salt Data: HCl

DETAILS

MP Biomedicals - 02190244

Hydrochloride
Cerebral and coronary vasodilator with calcium blocking activity. Structurally related to Nifedipine.

Sigma Aldrich - N7510

Biochem/physiol Actions
Blocks L-type voltage-dependent calcium channels; antihypertensive.

Toronto Research Chemicals - N394500

Dihydropyridine calcium channel blocker. Antianginal; antihypertensive.

REFERENCES

• Satoh, K., et al.: Clin. Exp. Pharmacol. Physiol., 7, 249 (1980)
• Sorkin, E.M., et al.: Drugs, 33, 296 (1980)