Product Name

  • Name

    Nicorandil

  • EINECS 265-514-1
  • CAS No. 65141-46-0
  • Article Data12
  • CAS DataBase
  • Density 1.331 g/cm3
  • Solubility
  • Melting Point 92 °C
  • Formula C8H9N3O4
  • Boiling Point 456.7 °C at 760 mmHg
  • Molecular Weight 211.177
  • Flash Point 230 °C
  • Transport Information
  • Appearance White solid
  • Safety 26-39
  • Risk Codes 22-41
  • Molecular Structure Molecular Structure of 65141-46-0 (Nicorandil)
  • Hazard Symbols Xn
  • 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;
  • PSA 97.04000
  • LogP 0.93380

Synthetic route

N-(2-hydroxyethyl)nicotinamide
6265-73-2

N-(2-hydroxyethyl)nicotinamide

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
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
40055-37-6

2-(pyridin-3-yl)-4,5-dihydrooxazole

isopentyl nitrite
110-46-3

isopentyl nitrite

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
In 1,4-dioxane at 100℃; for 5h;80%
2-(pyridin-3-yl)-4,5-dihydrooxazole
40055-37-6

2-(pyridin-3-yl)-4,5-dihydrooxazole

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
With tert.-butylnitrite; oxygen In 1,4-dioxane at 60℃; Sealed tube; Green chemistry;73%
tert.-butylnitrite
540-80-7

tert.-butylnitrite

2-(pyridin-3-yl)-4,5-dihydrooxazole
40055-37-6

2-(pyridin-3-yl)-4,5-dihydrooxazole

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
In toluene at 100℃; for 5h;60%
pyridine-3-carbonyl chloride hydrochloride
20260-53-1

pyridine-3-carbonyl chloride hydrochloride

2-nitroxyethylammonium nitrate
4665-58-1

2-nitroxyethylammonium nitrate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
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
614-18-6

3-pyridinecarboxylic acid ethyl ester

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 18 h / 20 - 55 °C
2: nitric acid / 2 h / -5 °C
View Scheme
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
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
500-22-1

3-pyridinecarboxaldehyde

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

Conditions
ConditionsYield
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
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

salicylic acid
69-72-7

salicylic acid

C8H9N3O4*C7H6O3

C8H9N3O4*C7H6O3

Conditions
ConditionsYield
In water; acetonitrile Solvent;95%
In water at 20℃; for 48h;55.9%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

N-(2-nitroxyethyl)isonicotinamide
65141-47-1

N-(2-nitroxyethyl)isonicotinamide

palladium dichloride

palladium dichloride

trans-[(2-nitroxyethyl)isonicotinamide-N'][(2-nitroxyethyl)nicotinamide-N]dichloropalladium(II)

trans-[(2-nitroxyethyl)isonicotinamide-N'][(2-nitroxyethyl)nicotinamide-N]dichloropalladium(II)

Conditions
ConditionsYield
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)
10025-99-7

potassium tetrachloroplatinate(II)

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

PtCl2(C8H9N3O4)2
203808-46-2

PtCl2(C8H9N3O4)2

Conditions
ConditionsYield
In water ppt. washing (H2O, EtOH, Et2O); elem. anal.;92%
rhodium(II) pivalate

rhodium(II) pivalate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

[(NC5H4C(O)NHCH2CH2ONO2)2Rh2(OOCC(CH3)3)4]
186506-79-6

[(NC5H4C(O)NHCH2CH2ONO2)2Rh2(OOCC(CH3)3)4]

Conditions
ConditionsYield
In tetrahydrofuran room temperature, pure Ar atmosphere; soln. evapn. to 1/3, crystals filtration off, air drying, recrystn. (THF); elem. anal.;90%
iodomethyl isopropylcarbamate
1402915-01-8

iodomethyl isopropylcarbamate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

1-(((isopropylcarbamoyl)oxy)methyl)-3-((2-(nitroxy)ethyl)carbamoyl)pyridine-1-ium iodide
1402916-59-9

1-(((isopropylcarbamoyl)oxy)methyl)-3-((2-(nitroxy)ethyl)carbamoyl)pyridine-1-ium iodide

Conditions
ConditionsYield
In acetonitrile at 20℃;88%
In acetonitrile at 20℃;88%
sodium tetrachloroplatinate(II)

sodium tetrachloroplatinate(II)

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

N-(2-nitroxyethyl)isonicotinamide
65141-47-1

N-(2-nitroxyethyl)isonicotinamide

trans-[(2-nitroxyethyl)isonicotinamide-N'][(2-nitroxyethyl)nicotinamide-N]dichloroplatinum(II)
365515-47-5

trans-[(2-nitroxyethyl)isonicotinamide-N'][(2-nitroxyethyl)nicotinamide-N]dichloroplatinum(II)

Conditions
ConditionsYield
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
353736-55-7

iodomethyl diisopropylcarbamate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

1-(((diisopropylcarbamoyl)oxy)methyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

1-(((diisopropylcarbamoyl)oxy)methyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

Conditions
ConditionsYield
In acetonitrile at 20℃;85%
iodomethyl 1-piperidinyl carbamate

iodomethyl 1-piperidinyl carbamate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

3-((2-(nitrooxy)ethyl)carbamoyl)-1-(((piperidine-1-carbonyl)oxy)methyl)pyridin-1-ium iodide

3-((2-(nitrooxy)ethyl)carbamoyl)-1-(((piperidine-1-carbonyl)oxy)methyl)pyridin-1-ium iodide

Conditions
ConditionsYield
In acetonitrile at 20℃;84%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

ethoxycarbonyloxymethyl iodide
82619-14-5

ethoxycarbonyloxymethyl iodide

1-(((ethoxycarbonyl)oxy)methyl)-3 -((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

1-(((ethoxycarbonyl)oxy)methyl)-3 -((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

Conditions
ConditionsYield
In acetonitrile at 20℃;77%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

1-hydroxy-2-naphthoic acid
86-48-6

1-hydroxy-2-naphthoic acid

nicorandil 1-hydroxy-2-naphthoic acid

nicorandil 1-hydroxy-2-naphthoic acid

Conditions
ConditionsYield
In water at 20℃; for 48h;75.8%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

copper(ll) bromide
7789-45-9

copper(ll) bromide

(NC5H4C(O)NHCH2CH2ONO2)2CuBr2
186506-76-3

(NC5H4C(O)NHCH2CH2ONO2)2CuBr2

Conditions
ConditionsYield
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%
copper(II) pivalate dimer

copper(II) pivalate dimer

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

[(NC5H4C(O)NHCH2CH2ONO2)2Cu2(OOCC(CH3)3)4]
186506-77-4

[(NC5H4C(O)NHCH2CH2ONO2)2Cu2(OOCC(CH3)3)4]

Conditions
ConditionsYield
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
258841-42-8

isopropyloxycarbonyloxymethyl iodide

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

1-(((isopropoxycarbonyl)oxy)methyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

1-(((isopropoxycarbonyl)oxy)methyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

Conditions
ConditionsYield
In acetonitrile at 20℃;60%
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

C7H6O4*C8H9N3O4

C7H6O4*C8H9N3O4

Conditions
ConditionsYield
In water at 20℃; for 48h;54.7%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

tert-butyl (iodomethyl) carbonate
184373-03-3

tert-butyl (iodomethyl) carbonate

1-(((tert-butoxycarbonyl)oxy)methyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

1-(((tert-butoxycarbonyl)oxy)methyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

Conditions
ConditionsYield
54%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

3-Carboxyphenol
99-06-9

3-Carboxyphenol

C7H6O3*C8H9N3O4

C7H6O3*C8H9N3O4

Conditions
ConditionsYield
In water at 20℃; for 48h;42%
[Ni9(HOOCCMe3)4(μ4-O)3(μ3-OH)3(μ-O,O-OOCCMe3)(μ-O,O'-OOCCMe3)7(μ3-O,O,O'-OOCCMe3)3(μ4-O,O,O',O'-OOCCMe3)]

[Ni9(HOOCCMe3)4(μ4-O)3(μ3-OH)3(μ-O,O-OOCCMe3)(μ-O,O'-OOCCMe3)7(μ3-O,O,O'-OOCCMe3)3(μ4-O,O,O',O'-OOCCMe3)]

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

(C5H4NC(O)NHCH2CH2ONO2)4Ni2((CH3)3CCOO)4(OH)*C4H8O*2H2O

(C5H4NC(O)NHCH2CH2ONO2)4Ni2((CH3)3CCOO)4(OH)*C4H8O*2H2O

Conditions
ConditionsYield
In toluene stirring (20°C, 0.5 h); evapn., extn. (THF/benzene), crystn. (5°C); elem. anal.;40%
1-iodoethyl diisopropylcarbamate

1-iodoethyl diisopropylcarbamate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

1-(1-((diisopropylcarbamoyl)oxy)ethyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

1-(1-((diisopropylcarbamoyl)oxy)ethyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridin-1-ium iodide

Conditions
ConditionsYield
In acetonitrile at 20℃;35%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

methyl iodide
74-88-4

methyl iodide

1-(2-(nicotinamido)ethyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridine-1-indole iodide

1-(2-(nicotinamido)ethyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridine-1-indole iodide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 336h; pH=7.0 - 9.0; Solvent; Cooling with ice;2.25%
methyl bromide
74-83-9

methyl bromide

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

1-(2-(nicotinamido)ethyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridine-1-indole iodide

1-(2-(nicotinamido)ethyl)-3-((2-(nitrooxy)ethyl)carbamoyl)pyridine-1-indole iodide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 240h; pH=7.0 - 9.0; Darkness;1.9%
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

2-(pyridin-3-yl)-4,5-dihydrooxazole
40055-37-6

2-(pyridin-3-yl)-4,5-dihydrooxazole

Conditions
ConditionsYield
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
65141-46-0

N-(2-nitroxyethyl)nicotinamide

2-aminoethyl nicotinate nitrate
88598-33-8

2-aminoethyl nicotinate nitrate

Conditions
ConditionsYield
With water at 70℃; for 4h;40 mg
N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

A

Polymer, M.w. 30,000-50,000; Monomer(s): N-(2-nitroxyethyl)nicotinamide

Polymer, M.w. 30,000-50,000; Monomer(s): N-(2-nitroxyethyl)nicotinamide

B

Polymer, M.w. 1000; Monomer(s): 2-(3-pyridyl)-4,5-dihydrooxazole

Polymer, M.w. 1000; Monomer(s): 2-(3-pyridyl)-4,5-dihydrooxazole

Conditions
ConditionsYield
at 70℃; for 72h; Polymerization;
cobalt pivalate

cobalt pivalate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

(nicorandil)Co(μ-OOCCMe3)4Co(nicorandil)
251911-24-7

(nicorandil)Co(μ-OOCCMe3)4Co(nicorandil)

Conditions
ConditionsYield
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);
cobalt pivalate

cobalt pivalate

N-(2-nitroxyethyl)nicotinamide
65141-46-0

N-(2-nitroxyethyl)nicotinamide

(nicorandil)2(OOCCMe3)Co(μ-OH2)(μ-OOCCMe3)2Co(OOCCMe3)(nicorandil)2

(nicorandil)2(OOCCMe3)Co(μ-OH2)(μ-OOCCMe3)2Co(OOCCMe3)(nicorandil)2

Conditions
ConditionsYield
In water soln. of ligand addn. to soln. of Co-compd., soln. keeping at room temperature (5 d); solvent removal; elem. anal.;

Nicorandil Chemical Properties

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 Uses

 Nicorandil (CAS NO.65141-46-0) is used as an antianginal .

Nicorandil 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.

Nicorandil 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.

Nicorandil 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.

Nicorandil 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.

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