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21829-25-4

Basic Information
CAS No.: 21829-25-4
Name: Nifedipine
Article Data: 71
Molecular Structure:
Molecular Structure of 21829-25-4 (Nifedipine)
Formula: C17H18N2O6
Molecular Weight: 346.34
Synonyms: Fenamon;Fenihidine;Hadipine;Introcar;Macorel;Myogard;Nedipin;Nicardia retard;Nifar;Nifebene;Nifecor;Nifedepat;Nifedin;Nifedipine;Nifedipres;Nifelan;Adalat LA;Adalat LP;Adalat Oros;
EINECS: 244-598-3
Density: 1.271 g/cm3
Melting Point: 171-175 °C
Boiling Point: 475.3 °C at 760 mmHg
Flash Point: 241.2 °C
Solubility: soluble in DMSO
Appearance: yellow crystalline solid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36
PSA: 110.45000
LogP: 3.02760
Synthetic route
105-45-3

acetoacetic acid methyl ester

552-89-6

2-nitro-benzaldehyde

21829-25-4

nifedipine

Conditions
ConditionsYield
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis;95%
With ammonium acetate; sodium dodecyl-sulfate; toluene-4-sulfonic acid for 1h; Hantzsch reaction; ultrasonic irradiation;92%
With ammonium acetate at 75℃; for 3h; Hantzsch reaction; Neat (no solvent);92%
126192-87-8

1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylenemethaneamine

105-45-3

acetoacetic acid methyl ester

14205-39-1

methyl 3-aminocrotonate

21829-25-4

nifedipine

Conditions
ConditionsYield
In methanol for 36h; Heating;82.6%
126192-87-8

1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylenemethaneamine

14205-39-1

methyl 3-aminocrotonate

21829-25-4

nifedipine

Conditions
ConditionsYield
In methanol; acetic acid82.6%
105-45-3

acetoacetic acid methyl ester

552-89-6

2-nitro-benzaldehyde

14205-39-1

methyl 3-aminocrotonate

21829-25-4

nifedipine

Conditions
ConditionsYield
In ethanol Heating;80%
With sodium tosylate In water for 0.3h; Time; Hantzsch Dihydropyridine Synthesis; Microwave irradiation; Reflux; Green chemistry;42%

1-(2'-nitrophenyl)-N,N'-bis-(2'-nitrophenyl) methylene methanediamine

105-45-3

acetoacetic acid methyl ester

14205-39-1

methyl 3-aminocrotonate

21829-25-4

nifedipine

Conditions
ConditionsYield
In methanol; acetic acid78.5%

1-(2'-nitrophenyl)-N,N'-bis-(2'-nitrophenyl) methylene methanediamine

105-45-3

acetoacetic acid methyl ester

21829-25-4

nifedipine

Conditions
ConditionsYield
With ammonium hydroxide In methanol; acetic acid76%
21731-17-9

methyl 3-aminocrotonate

124732-84-9

2-(o-nitro)phenyl-tetrahydro-(2H)-1,3-oxazine

21829-25-4

nifedipine

Conditions
ConditionsYield
In acetonitrile; trifluoroacetic acid for 12h; Ambient temperature;75%
126192-88-9

1-(2'-nitrophenyl)-N,N-bis-(2'-nitrophenyl)methylenemethanediamine

105-45-3

acetoacetic acid methyl ester

14205-39-1

methyl 3-aminocrotonate

21829-25-4

nifedipine

Conditions
ConditionsYield
In methanol for 46h;75%
126192-87-8

1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylenemethaneamine

105-45-3

acetoacetic acid methyl ester

21829-25-4

nifedipine

Conditions
ConditionsYield
With ammonia In methanol; acetic acid74%
With ammonia In methanol71%
In methanol for 36h; Mechanism; Heating;
21731-17-9

methyl 3-aminocrotonate

124732-83-8

2-(o-nitro)phenyl-4,4-dimethyloxazolidine

21829-25-4

nifedipine

Conditions
ConditionsYield
In acetonitrile; trifluoroacetic acid for 10h; Ambient temperature;70%
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Chemistry


IUPAC Name: dimethyl2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
Empirical Formula: C17H18N2O6
Molecular Weight: 346.3346
EINECS: 244-598-3
Melting Point: 171-175 °C 
Storage temp: 2-8 °C
Water Solubility: <0.1 g/100 mL at 19.5 °C 
Index of Refraction: 1.558 
Molar Refractivity: 87.9 cm3 
Molar Volume: 272.2 cm 
Surface Tension: 46 dyne/cm 
Density: 1.271 g/cm
Flash Point:  241.2 °C 
Enthalpy of Vaporization: 73.87 kJ/mol 
Boiling Point:  475.3 °C at 760 mmHg 
Vapour Pressure: 3.37E-09 mmHg at 25 °C
XLogP3-AA: 2.2
H-Bond Donor: 1
H-Bond Acceptor: 7
Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
InChI: InChI=1S/C17H18N2O6/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/h5-8,15,18H,1-4H3  
InChIKey: HYIMSNHJOBLJNT-UHFFFAOYSA-N
Product Categories of Adalat (CAS NO.21829-25-4): Pharmaceutical; Active Pharmaceutical Ingredients; Dihydropyridine Class Chemicals; Functional Materials; Photopolymerization Initiators; Intermediates & Fine Chemicals; Pharmaceuticals; Calcium channel; Ion Channels               

Uses

  Adalat (CAS NO.21829-25-4)'s  main uses are as an antianginal (especially in Prinzmetal's angina) and antihypertensive, although a large number of other uses have recently been found for this agent, such as Raynaud's phenomenon, premature labor, and painful spasms of the esophagus in cancer and tetanus patients. It is also commonly used for the small subset of pulmonary hypertension patients whose symptoms respond to calcium channel blockers.
The approved uses forAdalat are the long-term treatment of hypertension (high blood pressure) and angina pectoris.
 Adalat has been used frequently as a tocolytic (agent that delays premature labor). A Cochrane review has concluded that it is comparable with magnesium sulfate and beta-agonists (such as ritodrine) with fewer side-effects. Its role vis à vis atosiban is not established. It is also used in high-altitude medicine to treat high altitude pulmonary edema.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 100mg/kg (100mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
cat LDLo intravenous 500ug/kg (0.5mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
child TDLo oral 70mg/kg (70mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

ENDOCRINE: HYPERGLYCEMIA
Pediatrics. Vol. 86, Pg. 91, 1990.
man TDLo oral 143ug/kg (0.143mg/kg)   Archives of Internal Medicine. Vol. 158, Pg. 1379, 1998.
man TDLo oral 143ug/kg/1D (0.143mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 380, 1972.
man TDLo oral 714ug/kg (0.714mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Emergency Medicine. Vol. 22, Pg. 196, 1993.
man TDLo oral 1143ug/kg/2D- (1.143mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
American Journal of Medicine. Vol. 81, Pg. 705, 1986.
man TDLo oral 8571ug/kg (8.571mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Human & Experimental Toxicology. Vol. 9, Pg. 309, 1990.
man TDLo oral 34286ug/kg (34.286mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: NECROTIC GHANGES
Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 725, 1995.
man TDLo oral 105mg/kg/26W- (105mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Lancet. Vol. 339, Pg. 1382, 1992.
mouse LD50 intraperitoneal 185mg/kg (185mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION
Pharmaceutical Chemistry Journal Vol. 16, Pg. 817, 1982.
mouse LD50 intravenous 4200ug/kg (4.2mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
mouse LD50 oral 202mg/kg (202mg/kg)   United States Patent Document. Vol. #3644627,
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1831, 1971.
rabbit LD50 intravenous 2mg/kg (2mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
rabbit LD50 oral 504mg/kg (504mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 915, 1985.
rat LD50 intraperitoneal 230mg/kg (230mg/kg)   Yakkyoku. Pharmacy. Vol. 28, Pg. 1451, 1977.
rat LD50 intravenous 6mg/kg (6mg/kg)   Archives of Toxicology. Vol. 54, Pg. 275, 1983.
rat LD50 oral 1022mg/kg (1022mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1831, 1971.
women TDLo oral 600ug/kg/45M- (0.6mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: NAUSEA OR VOMITING
Archives of Internal Medicine. Vol. 147, Pg. 556, 1987.
women TDLo oral 800ug/kg/1D-I (0.8mg/kg) BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)"

BEHAVIORAL: HEADACHE

GASTROINTESTINAL: NAUSEA OR VOMITING
Postgraduate Medical Journal. Vol. 62, Pg. 1029, 1986.
women TDLo oral 2400ug/kg/3D- (2.4mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS British Medical Journal. Vol. 304, Pg. 1225, 1992.
women TDLo oral 11200ug/kg (11.2mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Japanese Journal of Toxicology. Vol. 5, Pg. 79, 1992.
women TDLo oral 31mg/kg/11W-I (31mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Heart Journal. Vol. 108, Pg. 611, 1984.

Consensus Reports

 Adalat  is reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: decreased blood pressure, BP lowering, cardiomyopathy, changes in regional blood flow, hyperglycemia, nausea or vomiting, respiratory depression, toxic psychosis. An experimental teratogen. Experimental reproductive effects. See also ESTERS. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: XnHarmful,XiIrritant
Risk Statements: 22-36/37/38 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 1
RTECS: US7975000

Specification

 Adalat , its CAS NO. is 21829-25-4, the synonyms are Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-3,5-pyridinedicarboxylate ; 1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester ; Nifedipine ;  3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester .

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