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Nitrendipine

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Name

Nitrendipine

EINECS 254-513-1
CAS No. 39562-70-4 Density 1.247 g/cm3
PSA 110.45000 LogP 3.41770
Solubility methanol: 15 mg/mL Melting Point 158 °C
Formula C18H20N2O6 Boiling Point 488.9 °C at 760 mmHg
Molecular Weight 360.367 Flash Point 249.5 °C
Transport Information N/A Appearance Crystalline solid
Safety 36 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 39562-70-4 (Nitrendipine) Hazard Symbols HarmfulXn
Synonyms

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, ethyl methyl ester (9CI);BAY-e 5009;Bayotensin;Baypress;Bylotensin;Deiten;Nidrel;Nitrendipin;Nitrepin;

Article Data 29

Nitrendipine Synthetic route

141-97-9

ethyl acetoacetate

99-61-6

3-nitro-benzaldehyde

14205-39-1

methyl 3-aminocrotonate

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With sodium tosylate In water for 0.4h; Reagent/catalyst; Time; Hantzsch Dihydropyridine Synthesis; Microwave irradiation; Reflux; Green chemistry;94%
With C21H38N(1+)*Mo11O40PV(4-)*3H(1+) In ethanol at 78℃; for 8h; Catalytic behavior; Hantzsch Pyridine Synthesis; Green chemistry;78%
Hantzsch Dihydropyridine Synthesis; Darkness; Reflux;59%

Benzyl-{2-[5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-ethyl}-dimethyl-ammonium; iodide

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 25℃;92%

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

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 25℃; for 24h;92%
Multi-step reaction with 3 steps
1: 67 percent / KOH / tetrahydrofuran / 24 h / 25 °C
2: 93 percent / acetone / Heating
3: 92 percent / KOH / ethanol / 25 °C
View Scheme
67-56-1

methanol

C23H27N4O6(1+)*F6P(1-)

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With sodium methylate for 16h; Reflux;92%

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

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 25℃;91%
Multi-step reaction with 3 steps
1: 32 percent / KOH / tetrahydrofuran / 25 °C
2: 93 percent / acetone / Heating
3: 92 percent / KOH / ethanol / 25 °C
View Scheme

ethyl aminocrotonate

119128-13-1

methyl (Z)-2-(3-nitrobenzylidene)-3-oxobutanoate

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
In isopropyl alcohol for 10h; Heating / reflux;89%
39562-17-9

methyl 2-(3-nitrophenylmethylene)acetoacetate

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
In ethanol for 6h; Reflux;86%
at 90℃; for 0.15h; Microwave irradiation;
21731-17-9

methyl 3-aminocrotonate

39562-16-8

ethyl 2-[(3-Nitrophenyl)methylene]-3-oxobutanoate

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
Stage #1: methyl 3-aminocrotonate; ethyl 2-[(3-Nitrophenyl)methylene]-3-oxobutanoate In ethanol at 75 - 80℃; for 1h;
Stage #2: With acetic anhydride In ethanol at 75 - 80℃; for 1h; Solvent;
86%

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

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 25℃;85%
Multi-step reaction with 3 steps
1: 26 percent / KOH / tetrahydrofuran / 25 °C
2: 93 percent / acetone / Heating
3: 92 percent / KOH / ethanol / 25 °C
View Scheme
39562-16-8

ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate

14205-39-1

methyl 3-aminocrotonate

39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
Stage #1: ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate; methyl 3-aminocrotonate In ethanol at 70 - 75℃; for 1h;
Stage #2: With hydrogenchloride In ethanol; water at 70 - 75℃;
80%
In ethanol for 8h; Heating;79%
With acetic acid; N-ethyl-N,N-diisopropylamine In ethanol Reflux;

Nitrendipine Specification

The nitrendipine , with the CAS register number 39562-70-4, has other name as nitrendipine ; 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5 pyridinedicarboxylicacidethy ; baye5009 ; bayotensin ; baypress ; ethylmethyl1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxy ; lmethylester ; nidrel .

The physical properties of this chemcial are as followings: (1)ACD/LogP:  3.50 ; (2)ACD/LogD (pH 5.5):  3.5  ; (3)ACD/LogD (pH 7.4):  3.5  ; (4)ACD/BCF (pH 5.5):  267.27  ; (5)ACD/BCF (pH 7.4):  267.77  ; (6)ACD/KOC (pH 5.5):  1899.24  ; (7)ACD/KOC (pH 7.4):  1902.83  ; (8)#H bond acceptors:  8  ; (9)#H bond donors:  1  ; (10)#Freely Rotating Bonds:  7  ; (11)Polar Surface Area:  101.66 ; (12)Index of Refraction:  1.553  ; (13)Molar Refractivity:  92.53 cm ; (14)Molar Volume:  288.7 cm3  ; (15)Polarizability:  36.68× 10-24 cm ; (16)Surface Tension:  45.3 dyne/cm  ; (17)Density:  1.247 g/cm3  ; (18)Flash Point:  249.5 °C  ; (19)Enthalpy of Vaporization:  75.51 kJ/mol  ; (20)Boiling Point:  488.9 °C at 760 mmHg  ; (21)Vapour Pressure:  1.04E-09 mmHg at 25°C.

This is a kind of yellow crystalline powder with no odour and no taste. When meets with light, it will to bad and it is soluble in acetone and chloroform but slightly soluble in methyl alcohol or ethanol and insoluble in water. As to its product categories, there are various, including Pharmaceutical;Intermediates & Fine Chemicals;Pharmaceuticals;Calcium channel;Ion Channels.

Being a kind of harmful chemical, it may cause damage to health and it is also harmful if by inhalation, in contact with skin or if swallowed. So while dealing with this chemical, you should be cautious. Wear suitable protective clothing and if you need more safety information, you could go to WGK Germany  1. As for its raw materials, there are including Ethyl acetoacetate, Methyl acetoacetate, 3-Nitrobenzaldehyde, Methyl 3-aminocrotonate.

As for its usage, it is the second generation CCB - calcium-channel blockers, to be as the ideal drugs to cure hypertension, as it has the function of depressurization and vasoconstriction. Besides, it is used for various types of hypertension, such as the primary and secondary light, medium pressure, and it is also be used to coronary heart disease, and congestive heart failure.

Additionally, you could convert the following data information into the molecular structure:
SMILES:O=C(OCC)\C1=C(\N/C(=C(/C(=O)OC)C1c2cccc([N+]([O-])=O)c2)C)C
InChI:InChI=1/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3
InChIKey:PVHUJELLJLJGLN-UHFFFAOYAU

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 2500ug/kg (2.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
"Nitrendipine, Based on Presentations at International Workshop on Nitrendipine, 1st, New York, 1982," Scriabine, A., et al., eds., Baltimore, Urban & Schwarzenberg, 1984Vol. -, Pg. 25, 1984.
dog LD50 oral > 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING "Nitrendipine, Based on Presentations at International Workshop on Nitrendipine, 1st, New York, 1982," Scriabine, A., et al., eds., Baltimore, Urban & Schwarzenberg, 1984Vol. -, Pg. 25, 1984.
mouse LD50 intraperitoneal 303mg/kg (303mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: CHANGES IN SPLEEN
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 121, 1988.
mouse LD50 intravenous 34500ug/kg (34.5mg/kg)   Farmaco, Edizione Scientifica. Vol. 42, Pg. 697, 1987.
 
mouse LD50 oral 2540mg/kg (2540mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
"Nitrendipine, Based on Presentations at International Workshop on Nitrendipine, 1st, New York, 1982," Scriabine, A., et al., eds., Baltimore, Urban & Schwarzenberg, 1984Vol. -, Pg. 25, 1984.
mouse LD50 subcutaneous 7613mg/kg (7613mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: CHANGES IN SPLEEN

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 121, 1988.
rabbit LD50 intravenous 2500ug/kg (2.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
"Nitrendipine, Based on Presentations at International Workshop on Nitrendipine, 1st, New York, 1982," Scriabine, A., et al., eds., Baltimore, Urban & Schwarzenberg, 1984Vol. -, Pg. 25, 1984.
rabbit LD50 oral 2500mg/kg (2500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: REGIDITY
"Nitrendipine, Based on Presentations at International Workshop on Nitrendipine, 1st, New York, 1982," Scriabine, A., et al., eds., Baltimore, Urban & Schwarzenberg, 1984Vol. -, Pg. 25, 1984.

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