Nimodipine supplier | CasNO.66085-59-4

Name
Nimodipine
EINECS 266-127-0
CAS No. 66085-59-4
Article Data12
CAS DataBase
Density 1.212 g/cm³
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
Appearance Crystalline solid
Safety 36
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols Xn
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;
PSA 119.68000
LogP 3.82280

Synthetic route

: 40100-28-5
isopropyl 3-aminocrotonate

: 39562-22-6
(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate

: 66085-59-4
nimodipin

Conditions

Conditions	Yield
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

Conditions	Yield
In ethanol for 16h; Heating;	A 69% B n/a

...Expand

: 542-08-5
isopropyl acetoacetate

: 22502-03-0
2-methoxyethyl-3-oxobutanoate

: 99-61-6
3-nitro-benzaldehyde

: 66085-59-4
nimodipin

Conditions

Conditions	Yield
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;

...Expand

: 542-08-5
isopropyl acetoacetate

: 66085-59-4
nimodipin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

: 66085-59-4
nimodipin

: 22128-62-7
carbonochloridic acid, chloromethyl ester

: C23H27ClN2O9

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Cooling with ice;	95%
Stage #1: nimodipin With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: carbonochloridic acid, chloromethyl ester In tetrahydrofuran at 20℃;	94.84%

: 66085-59-4
nimodipin

: 3-isopropyl 5-(2-methoxyethyl) 2,6-bis(methyl-d3)-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Conditions

Conditions	Yield
With TFA-d; water-d2 In 1-methyl-pyrrolidin-2-one at 50℃; for 24h; Schlenk technique; Inert atmosphere;	94%

: 66085-59-4
nimodipin

: 85677-93-6
Nimodipine Oxidized

Conditions

Conditions	Yield
With potassium carbonate; eosin Y bis(tetrabutyl ammonium salt) In methanol; water at 20℃; for 12h; Irradiation; Green chemistry;	78%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 12h;	78.4%
With nitric acid at 100℃; for 1h;	71%

: 50-00-0
formaldehyd

: 66085-59-4
nimodipin

: 4-(3-Dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

Conditions

Conditions	Yield
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 30h;	77%
With sodium carbonate In water; dimethyl sulfoxide at 130℃; for 15h; Schlenk technique; Sealed tube; Green chemistry;	48%

: 66085-59-4
nimodipin

: 229625-50-7
di-tert-butyl chloromethyl phosphate

: C30H45N2O11P

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	55%

: 50893-53-3
carbonochloridic acid 1-chloro-ethyl ester

: 66085-59-4
nimodipin

: C24H29ClN2O9

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at -40 - 20℃;	52.7%

: 66085-59-4
nimodipin

: N-nitroso-nimodipine

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 37℃; for 6h; pH=3 - 3.5;	45%

: 66085-59-4
nimodipin

: 144476-58-4
2,6-Dimethyl-4-(4-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

Conditions

Conditions	Yield
In ethanol; water for 60h; Irradiation;

: 66085-59-4
nimodipin

A: 77940-92-2
(S)-Nimodipine

B: 77940-93-3
(R)-Nimodipine

Conditions

Conditions	Yield
With α1-acid glycoprotein HPLC column resolution of racemate;
With Chiralpak IC In hexane; isopropyl alcohol Reagent/catalyst; Solvent; Resolution of racemate;
With trifluoroacetic acid In methanol; isopropyl alcohol at 35℃; under 103432 Torr; Reagent/catalyst; Resolution of racemate; Supercritical conditions;

: 66085-59-4
nimodipin

: C4H9N2*ClH

: 85677-93-6
Nimodipine Oxidized

Conditions

Conditions	Yield
In ethanol at 37℃; for 2h; pH=7.4; Kinetics; Further Variations:; Reaction partners; Solvents;

: 66085-59-4
nimodipin

: C4H9N2O2*ClH

: 85677-93-6
Nimodipine Oxidized

Conditions

Conditions	Yield
With Britton-Robinson buffer In water; N,N-dimethyl-formamide at 37℃; pH=7.4; Kinetics;

: 66085-59-4
nimodipin

A: 2,6-dimethyl-4-(3-nitroso-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

B: 85677-93-6
Nimodipine Oxidized

Conditions

Conditions	Yield
In methanol Quantum yield; Product distribution; Further Variations:; Solvents; wavelengths; presence of air; Irradiation;

: 66085-59-4
nimodipin

A: 2,6-dimethyl-4-(3-nitroso-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-(2-methoxy-ethyl) ester

B: 116799-92-9
2-Methoxyethyl 1-Methylethyl 1,4-Dihydro-2,6-dimethyl-4-(3-hydroxylaminophenyl)-3,5-pyridinedicarboxylate

C: 85677-93-6
Nimodipine Oxidized

D: 155861-24-8
3-isopropyl 5-(2-methoxyethyl) 4-(3-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Conditions

Conditions	Yield
With triethylamine In acetonitrile Quantum yield; Irradiation;

...Expand

: 1333-82-0
chromium(VI) oxide

: 66085-59-4
nimodipin

: 85677-93-6
Nimodipine Oxidized

Conditions

Conditions	Yield
In acetic acid
In acetic acid

: 66085-59-4
nimodipin

: C25H31N3O11*ClH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 5 h / 55 - 60 °C 3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 5 h / 20 °C View Scheme

: 66085-59-4
nimodipin

: C26H33N3O11*ClH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 55 - 60 °C 3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 2 h / 20 °C View Scheme

: 66085-59-4
nimodipin

: C26H33N3O11*ClH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 4 h / 55 - 60 °C 3: hydrogenchloride / 1,4-dioxane; ethyl acetate / 2 h / 20 °C View Scheme

: 66085-59-4
nimodipin

: C29H39N3O11*ClH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 2: tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 50 - 60 °C 3: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 4 h / 20 °C View Scheme

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 NO_x.
Hazard Codes: Harmful Xn
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.

Product Name

Nimodipine

Synthetic route

Nimodipine Chemical Properties

Nimodipine Uses

Nimodipine Toxicity Data With Reference

Nimodipine Safety Profile

Nimodipine Specification

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