N-(2-hydroxyethyl)nicotinamide
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; |
2-(pyridin-3-yl)-4,5-dihydrooxazole
isopentyl nitrite
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In 1,4-dioxane at 100℃; for 5h; | 80% |
2-(pyridin-3-yl)-4,5-dihydrooxazole
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
With tert.-butylnitrite; oxygen In 1,4-dioxane at 60℃; Sealed tube; Green chemistry; | 73% |
tert.-butylnitrite
2-(pyridin-3-yl)-4,5-dihydrooxazole
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In toluene at 100℃; for 5h; | 60% |
pyridine-3-carbonyl chloride hydrochloride
2-nitroxyethylammonium nitrate
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 |
3-pyridinecarboxylic acid ethyl ester
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 |
pyridine-3-carbonitrile
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 |
3-pyridinecarboxaldehyde
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% |
N-(2-nitroxyethyl)nicotinamide
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% |
potassium tetrachloroplatinate(II)
N-(2-nitroxyethyl)nicotinamide
PtCl2(C8H9N3O4)2
Conditions | Yield |
---|---|
In water ppt. washing (H2O, EtOH, Et2O); elem. anal.; | 92% |
N-(2-nitroxyethyl)nicotinamide
[(NC5H4C(O)NHCH2CH2ONO2)2Rh2(OOCC(CH3)3)4]
Conditions | Yield |
---|---|
In tetrahydrofuran room temperature, pure Ar atmosphere; soln. evapn. to 1/3, crystals filtration off, air drying, recrystn. (THF); elem. anal.; | 90% |
iodomethyl isopropylcarbamate
N-(2-nitroxyethyl)nicotinamide
1-(((isopropylcarbamoyl)oxy)methyl)-3-((2-(nitroxy)ethyl)carbamoyl)pyridine-1-ium iodide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 88% |
In acetonitrile at 20℃; | 88% |
N-(2-nitroxyethyl)nicotinamide
N-(2-nitroxyethyl)isonicotinamide
trans-[(2-nitroxyethyl)isonicotinamide-N'][(2-nitroxyethyl)nicotinamide-N]dichloroplatinum(II)
Conditions | Yield |
---|---|
In ethanol; water aq. soln. of Pt complex added to a soln. of equimolar amts. of the ligands in 60% aq. EtOH at 20-30°C; stirred for 11 h; ppt. filtered off, washed with water and EtOH, and dried in air; elem. anal.; | 86% |
iodomethyl diisopropylcarbamate
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 85% |
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 84% |
N-(2-nitroxyethyl)nicotinamide
ethoxycarbonyloxymethyl iodide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 77% |
N-(2-nitroxyethyl)nicotinamide
1-hydroxy-2-naphthoic acid
Conditions | Yield |
---|---|
In water at 20℃; for 48h; | 75.8% |
N-(2-nitroxyethyl)nicotinamide
copper(ll) bromide
(NC5H4C(O)NHCH2CH2ONO2)2CuBr2
Conditions | Yield |
---|---|
In tetrahydrofuran pure Ar atmosphere, stirring (3 h), volume reduction (30-40°C, 0.1 torr), cooling to 5°C; ppt. washing (CH2Cl2), vacuum drying, recrystn. (2x, THF); elem. anal.; | 70.5% |
N-(2-nitroxyethyl)nicotinamide
[(NC5H4C(O)NHCH2CH2ONO2)2Cu2(OOCC(CH3)3)4]
Conditions | Yield |
---|---|
In tetrahydrofuran; benzene THF soln. of ligand addn. to benzene soln. of Cu-compd., pure Ar atmosphere; volume redn., recrystn. (THF); elem. anal.; | 70% |
isopropyloxycarbonyloxymethyl iodide
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 60% |
Conditions | Yield |
---|---|
In water at 20℃; for 48h; | 54.7% |
N-(2-nitroxyethyl)nicotinamide
tert-butyl (iodomethyl) carbonate
Conditions | Yield |
---|---|
54% |
Conditions | Yield |
---|---|
In water at 20℃; for 48h; | 42% |
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In toluene stirring (20°C, 0.5 h); evapn., extn. (THF/benzene), crystn. (5°C); elem. anal.; | 40% |
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 35% |
N-(2-nitroxyethyl)nicotinamide
methyl iodide
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 336h; pH=7.0 - 9.0; Solvent; Cooling with ice; | 2.25% |
methyl bromide
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 240h; pH=7.0 - 9.0; Darkness; | 1.9% |
N-(2-nitroxyethyl)nicotinamide
2-(pyridin-3-yl)-4,5-dihydrooxazole
Conditions | Yield |
---|---|
In sodium hydroxide at 60℃; for 5h; | 60 mg |
at 60℃; for 7h; Rate constant; Mechanism; Thermodynamic data; variation of pH; Δ Eexcit; |
N-(2-nitroxyethyl)nicotinamide
2-aminoethyl nicotinate nitrate
Conditions | Yield |
---|---|
With water at 70℃; for 4h; | 40 mg |
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
at 70℃; for 72h; Polymerization; |
N-(2-nitroxyethyl)nicotinamide
(nicorandil)Co(μ-OOCCMe3)4Co(nicorandil)
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene THF soln. of ligand addn. to THF soln. of Co-compd., boiling (15 min), solvent complete removal, residue dissoln. in boiling toluene, volume reduction (Ar flow), slow cooling to room temperature; ppt. sepn., washing (hexane), drying (Ar flow, room temperature); |
N-(2-nitroxyethyl)nicotinamide
Conditions | Yield |
---|---|
In water soln. of ligand addn. to soln. of Co-compd., soln. keeping at room temperature (5 d); solvent removal; elem. anal.; |
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
Nicorandil (CAS NO.65141-46-0) is used as an antianginal .
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.
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. |
Poison by ingestion. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. See also NITRATES.
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.
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