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| CAS No.: | 66085-59-4 |
|---|---|
| Name: | Nimodipine |
| Molecular Structure: | |
|
|
|
| Formula: | C21H26N2O7 |
| Molecular Weight: | 418.447 |
| 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; |
| EINECS: | 266-127-0 |
| Density: | 1.212 g/cm3 |
| Melting Point: | 125 °C |
| Boiling Point: | 534.8 °C at 760 mmHg |
| Flash Point: | 277.3 °C |
| Solubility: | methanol: 62.5 mg/mL |
| Appearance: | Crystalline solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 20/21/22 |
| Safety: | 36 |
| PSA: | 119.68000 |
| LogP: | 3.82280 |
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isopropyl 3-aminocrotonate
- 39562-22-6
(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate
- 66085-59-4
nimodipin
| 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 | Yield |
|---|---|
| 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 | 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; |
- 542-08-5
isopropyl acetoacetate
- 66085-59-4
nimodipin
| 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 | 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 |
- 66085-59-4
nimodipin
| Conditions | Yield |
|---|---|
| With sodium In 2-methoxy-ethanol; water |
- 66085-59-4
nimodipin
| Conditions | Yield |
|---|---|
| With sodium In 2-methoxy-ethanol; water |
- 39562-25-9
3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester
- 66085-59-4
nimodipin
| 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 | 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 | 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% |
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Chemistry
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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
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.
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. |
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: 
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
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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