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Nimodipine
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Name

Nimodipine

 EINECS 266-127-0
CAS No. 66085-59-4 Density 1.212 g/cm3
PSA 119.68000 LogP 3.82280
Solubility methanol: 62.5 mg/mL Melting Point 125 °C
Formula C21H26N2O7 Boiling Point 534.8 °C at 760 mmHg
Molecular Weight 418.447 Flash Point 277.3 °C
Transport Information N/A Appearance Crystalline solid
Safety 36 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 66085-59-4 (Nimodipine) Hazard Symbols HarmfulXn
Synonyms

3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 1-methylethylester (9CI);Admon;3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl)5-(1-methylethyl) ester;Nimodipine AP;Nimotop;Periplum;

Article Data 12

Nimodipine Synthetic route

40100-28-5

isopropyl 3-aminocrotonate

39562-22-6

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate

66085-59-4

nimodipin

Conditions
ConditionsYield
In ethanol for 24h; Heating;81%
22502-03-0

2-methoxyethyl-3-oxobutanoate

99-61-6

3-nitro-benzaldehyde

143093-33-8

isopropyl β-aminocrotonate

A

66085-59-4

nimodipin

B

21881-78-7

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

Conditions
ConditionsYield
In ethanol for 16h; Heating;A 69%
B n/a
542-08-5

isopropyl acetoacetate

22502-03-0

2-methoxyethyl-3-oxobutanoate

99-61-6

3-nitro-benzaldehyde

66085-59-4

nimodipin

Conditions
ConditionsYield
With pyridine; 4 A molecular sieve; polysterene-based acid-cleavable Rink amine resin; trifluoroacetic acid 1) CH2Cl2, rt, 3 d; 2) 45 deg C, 24 h; 3) CH2Cl2, 45 min;; Yield given. Multistep reaction;
With ammonium acetate In ethanol at 80℃; for 2h; Hantzsch Pyridine Synthesis;
542-08-5

isopropyl acetoacetate

66085-59-4

nimodipin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NH3 (gas.) / 10 °C
2: 81 percent / ethanol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ammonia
2: ethanol / Reflux
View Scheme
22502-03-0

2-methoxyethyl-3-oxobutanoate

66085-59-4

nimodipin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77.5 percent / hydrogen chloride / toluene / 20 h / 10 °C
2: 81 percent / ethanol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ammonium hydroxide
2: piperidine / propionic acid / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: piperidine; acetic acid
2: ethanol / Reflux
View Scheme

(+)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl-2(S)-methoxy-2-phenylethyl ester

66085-59-4

nimodipin

Conditions
ConditionsYield
With sodium In 2-methoxy-ethanol; water

(-)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl-2(R)-methoxy-2-phenylethyl ester

66085-59-4

nimodipin

Conditions
ConditionsYield
With sodium In 2-methoxy-ethanol; water

(2′-methoxyethyl)-3-amino-3-methylacrylate

39562-25-9

3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester

66085-59-4

nimodipin

Conditions
ConditionsYield
With piperidine In propionic acid Reflux; Inert atmosphere;
14205-46-0

isopropyl 3-aminocrotonate

39562-22-6

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate

66085-59-4

nimodipin

Conditions
ConditionsYield
In ethanol Reflux;
66085-59-4

nimodipin

155861-24-8

3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 2844.3 Torr; for 2h;95%
With hydrogen In tetrahydrofuran; water at 120℃; under 37503.8 Torr; for 17h; chemoselective reaction;95%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 6h; Solvent; Inert atmosphere; Green chemistry; chemoselective reaction;90%

Nimodipine Chemical Properties


IUPAC Name: 5-O-(2-Methoxyethyl) 3-O-propan-2-yl2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Molecular Formula: C21H26N2O7
Molecular Weight: 418.44 g/mol
Canonical SMILES: c1([C@@H]2C(=C(NC(=C2C(OC(C)C)=O)C)C)C(OCCOC)=O)cc(ccc1)[N+](=O)[O-]
InChI: InChI=1/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3
EINECS: 266-127-0
Classification Code: Antihypertensive agents; Calcium channel blockers; Cardiovascular Agents; Drug / Therapeutic Agent; Membrane Transport Modulators; Reproductive Effect; Vasodilator; Vasodilator agents
Product Categories: Dihydropyridine Class Chemicals; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Calcium channel; Ion Channels
Melting Point: 125 °C
Solubility methanol: 62.5 mg/mL
Index of Refraction:  1.539 
Molar Refractivity:  108.14 cm3 
Molar Volume:  345 cm3 
Polarizability:  42.87×10-24 cm3 
Surface Tension:  43.8 dyne/cm 
Density:  1.212 g/cm3 
Flash Point:  277.3 °C 
Enthalpy of Vaporization:  81.11 kJ/mol 
Boiling Point:  534.8 °C at 760 mmHg 
Vapour Pressure of Nimodipine (CAS NO.66085-59-4): 1.63E-11 mmHg at 25°C

Nimodipine Uses

 Nimodipine's main use is in the prevention of cerebral vasospasm and resultant ischemia, a complication of subarachnoid hemorrhage (a form of cerebral bleed), specifically from ruptured intracranial berry aneurysms irrespective of the patient's post-ictus neurological condition.

Nimodipine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 4mg/kg (4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1733, 1986.
dog LD50 oral 1gm/kg (1000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 6899, 1985.
mouse LD50 intravenous 26200ug/kg (26.2mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 6899, 1985.
mouse LD50 oral 940mg/kg (940mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 6899, 1985.
mouse LD50 subcutaneous 9500mg/kg (9500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 6899, 1985.
rabbit LD50 intravenous 2500ug/kg (2.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1733, 1986.
rabbit LD50 oral 5gm/kg (5000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1733, 1986.
rat LD50 intravenous 5mg/kg (5mg/kg)   Archives of Toxicology. Vol. 54, Pg. 275, 1983.
rat LD50 oral 2738mg/kg (2738mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 6899, 1985.
rat LD50 subcutaneous 4234mg/kg (4234mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 6899, 1985.

Nimodipine Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: HarmfulXn
Risk Statements: 20/21/22 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36 
S36: Wear suitable protective clothing.
WGK Germany: 1
RTECS of Nimodipine (CAS NO.66085-59-4): US7975500

Nimodipine Specification

 Nimodipine (CAS NO.66085-59-4), its Synonyms are 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 1-methylethyl ester ; Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate ; Nimodipino ; Nimodipinum ; Nimotop ; Periplum . It is crystalline solid.

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