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| CAS No.: | 65141-46-0 |
|---|---|
| Name: | Nicorandil |
| Article Data: | 12 |
| Molecular Structure: | |
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| Formula: | C8H9N3O4 |
| Molecular Weight: | 211.177 |
| Synonyms: | 2-Nicotinamidoethylnitrate;Dancor;Ikorel;N-(2-Hydroxyethyl)nicotinamide nitrate;N-(2-Hydroxyethyl)nicotinamide nitrate ester;N-(2-Nitrooxyethyl)nicotinamide;3-Pyridinecarboxamide,N-[2-(nitrooxy)ethyl]-;Perisalol;SG 75;Sigmart;U 64417; |
| EINECS: | 265-514-1 |
| Density: | 1.331 g/cm3 |
| Melting Point: | 92 °C |
| Boiling Point: | 456.7 °C at 760 mmHg |
| Flash Point: | 230 °C |
| Appearance: | White solid |
| Hazard Symbols: | Xn |
| Risk Codes: | 22-41 |
| Safety: | 26-39 |
| PSA: | 97.04000 |
| LogP: | 0.93380 |
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- 6265-73-2
N-(2-hydroxyethyl)nicotinamide
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| With nitric acid; urea; europium(III) trifluoromethanesulfonate at 70℃; for 6h; Schlenk technique; | 86% |
| With nitric acid; propionic acid; propionic acid anhydride at 0 - 30℃; for 3.5h; Temperature; | 85.9% |
| With nitric acid at -5℃; for 2h; | 40% |
| Stage #1: N-(2-hydroxyethyl)nicotinamide With nitric acid; acetic anhydride; acetic acid at 15 - 22℃; Inert atmosphere; Stage #2: With ammonia In water at 5 - 35℃; for 1h; Product distribution / selectivity; |
- 40055-37-6
2-(pyridin-3-yl)-4,5-dihydrooxazole
- 110-46-3
isopentyl nitrite
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| In 1,4-dioxane at 100℃; for 5h; | 80% |
- 40055-37-6
2-(pyridin-3-yl)-4,5-dihydrooxazole
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| With tert.-butylnitrite; oxygen In 1,4-dioxane at 60℃; Sealed tube; Green chemistry; | 73% |
- 540-80-7
tert.-butylnitrite
- 40055-37-6
2-(pyridin-3-yl)-4,5-dihydrooxazole
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| In toluene at 100℃; for 5h; | 60% |
- 20260-53-1
pyridine-3-carbonyl chloride hydrochloride
- 4665-58-1
2-nitroxyethylammonium nitrate
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| With pyridine at 5 - 20℃; Inert atmosphere; | |
| Stage #1: pyridine-3-carbonyl chloride hydrochloride; 2-nitroxyethylammonium nitrate With pyridine at 5 - 20℃; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In chloroform |
- 614-18-6
3-pyridinecarboxylic acid ethyl ester
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 18 h / 20 - 55 °C 2: nitric acid / 2 h / -5 °C View Scheme |
- 100-54-9
pyridine-3-carbonitrile
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: zinc(II) chloride / chlorobenzene / 36 h / Inert atmosphere; Reflux 2: tert.-butylnitrite; oxygen / 1,4-dioxane / 60 °C / Sealed tube; Green chemistry View Scheme |
- 500-22-1
3-pyridinecarboxaldehyde
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: tetra-N-butylammonium tribromide / ethanol / 1 h / 20 °C 2: 1,4-dioxane / 5 h / 100 °C View Scheme |
| Conditions | Yield |
|---|---|
| In water; acetonitrile Solvent; | 95% |
| In water at 20℃; for 48h; | 55.9% |
- 65141-46-0
N-(2-nitroxyethyl)nicotinamide
- 65141-47-1
N-(2-nitroxyethyl)isonicotinamide
| Conditions | Yield |
|---|---|
| With conc. HCl In ethanol; water aq. soln. of PdCl2 added to a soln. of equimolar amts. of the ligands ina mixt.of EtOH:H2O (3:1) at 20-30°C; then conc. HCl added to pH 2-2.5; stirred for 2 h; ppt. filtered off, washed with water and EtOH, and dried in air; elem. anal.; | 94% |
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Chemistry
Structure of Nicorandil (CAS NO.65141-46-0):
IUPAC Name: 2-(pyridine-3-carbonylamino)ethyl nitrate
Empirical Formula: C8H9N3O4
Molecular Weight: 211.1748
EINECS: 265-514-1
Index of Refraction: 1.547
Molar Refractivity: 50.36 cm3
Molar Volume: 158.6 cm3
Polarizability: 19.96×10-24cm3
Surface Tension: 55.2 dyne/cm
Density: 1.331 g/cm3
Flash Point: 230 °C
Enthalpy of Vaporization: 71.67 kJ/mol
Melting Point: 92°C
Boiling Point: 456.7 °C at 760 mmHg
Vapour Pressure: 1.58E-08 mmHg at 25°C
Physical Appearance: White solid
Product Categories: Pharmaceutical;Intermediates & Fine Chemicals;Pharmaceuticals;Potassium channel
Synonyms of Nicorandil (CAS NO.65141-46-0): 2-(Nicotinamido)ethyl nitrat ; 2-Nicotinamidoethyl nitrate ; 3-Pyridinecarboxamide, N-(2-(nitroxy)ethyl)- ; N-(2-Hydroxyethyl)nicotinamide nitrate ; Nicorandilum
Uses
Nicorandil (CAS NO.65141-46-0) is used as an antianginal .
Production
Nicorandil acts by relaxing the smooth muscle of the blood vessels, especially those of the venous system. It does this through two methods. Firstly, by activating potassium channels, and secondly by donating nitric oxide to activate the enzyme guanylate cyclase. Guanylate cyclase causes activation of GMP leading to both arterial and venous vasodilatation. As it is selective for vascular potassium channels, it has no significant action on cardiac contractility and conduction.
Although it can dilate the coronary vessels of a healthy individual, its effects on the coronary vessels of someone with ischaemic heart disease will be little as they will already be completely dilated. Instead, it dilates the venous system, reducing preload and the work of the heart.
Toxicity Data With Reference
| 1. | orl-rat LD50:1220 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. | ||
| 2. | ipr-rat LD50:1100 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. | ||
| 3. | scu-rat LD50:1200 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. | ||
| 4. | orl-mus LD50:1150 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. | ||
| 5. | ipr-mus LD50:990 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. | ||
| 6. | scu-mus LD50:1350 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. | ||
| 7. | orl-dog LD50:62,500 µg/kg | YKYUA6 Yakkyoku. Pharmacy. 35 (1984),1627. |
Safety Profile
Poison by ingestion. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. See also NITRATES.
Specification
Common side effects include flushing, palpitation, weakness, headache, mouth ulcers, nausea and vomiting. More recently peri-anal, ileal and peri-stomal ulceration has been reported as a side effect. Anal ulceration is now included in the British National Formulary as a reported side effect. It can also give the feeling of severe toothache, and nasal congestion.