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55985-32-5

Basic Information
CAS No.: 55985-32-5
Name: Nicardipine
Article Data: 13
Molecular Structure:
Molecular Structure of 55985-32-5 (Nicardipine)
Formula: C26H29 N3 O6
Molecular Weight: 479.533
Synonyms: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl2-[methyl(phenylmethyl)amino]ethyl ester (9CI); (?à)-Nicardipine; Nicardipine; Perpidine
EINECS: 259-932-3
Density: 1.23 g/cm3
Melting Point: 136-138 ºC
Boiling Point: 603.4 °C at 760 mmHg
Flash Point: 318.7 °C
PSA: 113.69000
LogP: 4.52980
Synthetic route
103785-48-4

2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-[2-(toluene-4-sulfonyloxy)-ethyl] ester

103-67-3

benzyl-methyl-amine

55985-32-5

Nicardipine

Conditions
ConditionsYield
for 8h; Heating;77%
101-98-4

2-(N-benzyl-N-methyl)amino-1-ethanol

(S)-1,1-Dibenzyl-3-[(R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-piperidinium; bromide

55985-32-5

Nicardipine

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 25℃; for 24h;67%
101-98-4

2-(N-benzyl-N-methyl)amino-1-ethanol

(S)-1-Benzyl-3-[(R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-1-methyl-piperidinium; iodide

55985-32-5

Nicardipine

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 25℃;32%
101-98-4

2-(N-benzyl-N-methyl)amino-1-ethanol

(S)-1-Allyl-1-benzyl-3-[(R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-piperidinium; bromide

55985-32-5

Nicardipine

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 25℃;26%

3-Imino-butyric acid methyl ester; compound with acetic acid

2-Amino-4-(3-cyano-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-(3-nitrooxy-propyl) ester

55985-32-5

Nicardipine

Conditions
ConditionsYield
With sodium methylate In isopropyl alcohol Heating;

(R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-piperidin-3-yl) ester 5-methyl ester

55985-32-5

Nicardipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / CHCl3 / Heating
2: 67 percent / KOH / tetrahydrofuran / 24 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / CHCl3 / Heating
2: 26 percent / KOH / tetrahydrofuran / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / acetone / 8 h / Heating
2: 32 percent / KOH / tetrahydrofuran / 25 °C
View Scheme
88488-49-7

3-nitrooxypropyl acetoacetate

55985-32-5

Nicardipine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 38 percent / piperidine / benzene / 11 h / Heating
2: 30 percent / sodium methoxide / propan-2-ol / Heating
3: sodium methoxide / propan-2-ol / Heating
View Scheme
170748-98-8

3-nitroxypropyl 2-(3-cyanobenzylidene)acetoacetate

55985-32-5

Nicardipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 30 percent / sodium methoxide / propan-2-ol / Heating
2: sodium methoxide / propan-2-ol / Heating
View Scheme
85677-95-8

2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

55985-32-5

Nicardipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / 1.) Et3N; 2.) H2O / tetrahydrofuran / 1.) 1 h; 2.) 0.5 h
2: 77 percent / 8 h / Heating
View Scheme

(+)-2,6-dimethyl-3-methoxysulfonyl-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine

55985-32-5

Nicardipine

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Chemistry

IUPAC Name: 3-O-[2-[benzyl(methyl)amino]ethyl] 5-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Synonyms Methyl 2-(benzyl-methyl-amino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Product Categories: Active Pharmaceutical Ingredients
Molecular Structure: m-nitrobenzaldehyde as raw materials, condensation of acetyl chloride acid methyl ester with the amino-crotonic to get 2,6 - dimethyl -4 - (Inter-nitrophenyl) -1,4 - dihydro-pyridine 3,5 - 2-carboxylic acid - (2 - chloro) ethyl -5 - methyl ester, then condensation with benzyl amine nicardipine.
Molecular Formula: C26H29N3O6
Molecular Weight : 479.52
CAS NO: 55985-32-5
EINECS : 259-932-3
Mol File: 55985-32-5.mol
Melting point 136-138 ºC
Index of Refraction: 1.581
Surface Tension: 48.7 dyne/cm
Density: 1.23 g/cm3
Flash Point: 318.7 °C
Enthalpy of Vaporization: 89.75 kJ/mol
Boiling Point: 603.4 °C at 760 mmHg
Vapour Pressure: 1.63E-14 mmHg at 25°C
Appearance: Nicardipine Hydrochloride (CAS NO.55985-32-5) is yellow-green crystalline powder.

Uses

Nicardipine Hydrochloride (CAS NO.55985-32-5) is a new calcium antagonist, vasodilator,mainly used  for ischemic cerebrovascular disease and the treatment of essential hypertension.

Production

M-Nitrobenzaldehyde as raw materials, condensation of acetyl chloride acid methyl ester with the amino-crotonic to get 2,6 - dimethyl -4 - (Inter-nitrophenyl) -1,4 - dihydro-pyridine 3,5 - 2-carboxylic acid - (2 - chloro) ethyl -5 - methyl ester, then condensation with benzyl amine  nicardipine. Get Nicardipine Hydrochloride (CAS NO.55985-32-5) .

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 1250ug/kg (1.25mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING American Journal of Emergency Medicine. Vol. 18, Pg. 581, 2000.
mouse LD50 intravenous 9700ug/kg (9.7mg/kg)   United States Patent Document. Vol. #4672068,
mouse LD50 oral 305mg/kg (305mg/kg)   United States Patent Document. Vol. #4824855,
rat LD50 intravenous 11800ug/kg (11.8mg/kg)   United States Patent Document. Vol. #4710505,
rat LD50 oral 320mg/kg (320mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 915, 1985.