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Isosorbide 5-mononitrate

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CAS:16051-77-7
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CAS:16051-77-7
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CAS:16051-77-7
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Isosorbide 5-mononitrate manufacturers

Isosorbide 5-mononitrate Basic information
Product Name:Isosorbide 5-mononitrate
Synonyms:IMDUR;IS-5-MN;ISOSORBIDE MONONITRATE;ISOSORBIDE 5-MONONITRATE;ISOSORBIDE 5-NITRATE;ELANTAN;ELAN;CORANGIN
CAS:16051-77-7
MF:C6H9NO6
MW:191.14
EINECS:240-197-2
Product Categories:chiral;Nitric Oxide Reagents;Various Metabolites and Impurities;LEXAPRO;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;API's
Mol File:16051-77-7.mol
Isosorbide 5-mononitrate Structure
Isosorbide 5-mononitrate Chemical Properties
Melting point 88-93 °C
alpha 170 º (c=1, EtOH)
Boiling point 326.86°C (rough estimate)
density 1.5784 (rough estimate)
refractive index 145 ° (C=5, H2O)
storage temp. -20°C Freezer
solubility Undiluted isosorbide mononitrate is freely soluble in water, in acetone, in ethanol (96 per cent) and in methylene chloride. The solubility of the diluted product depends on the diluent and its concentration.
pka13.09±0.40(Predicted)
form Solid
color White to Off-White
Water Solubility soluble
Merck 5225
InChIKeyYWXYYJSYQOXTPL-SLPGGIOYSA-N
CAS DataBase Reference16051-77-7(CAS DataBase Reference)
EPA Substance Registry SystemD-Glucitol, 1,4:3,6-dianhydro-, 5-nitrate (16051-77-7)
Safety Information
Hazard Codes Xi-F,Xi,F
Risk Statements 36/37/38-11
Safety Statements 37/39-16-15
RIDADR 3251
RTECS LZ4386500
HazardClass 4.1
HS Code 2932999000
ToxicityLD50 oral in rat: 2010mg/kg
MSDS Information
ProviderLanguage
Isosorbide 5-mononitrate English
ACROS English
Isosorbide 5-mononitrate Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
Usesantidepressant, 5HT reuptake inhibitor
UsesIsosorbide 5-Mononitrate is a metabolite of Isosorbide Dinitrate; used as an antianginal.
UsesA metabolite of Isosorbide Dinitrate. Used as an antianginal
DefinitionChEBI: Isosorbide mononitrate is a nitrate ester and a glucitol derivative. It has a role as a nitric oxide donor and a vasodilator agent.
Brand nameImdur (Schering-Plough); Ismo (Dr. Reddy’s); Monoket (Schwarz Pharma) .
General DescriptionIsosorbide 5-mononitrate is a crystalline solid. Isosorbide 5-mononitrate is very flammable and may be toxic by ingestion.
Air & Water ReactionsHighly flammable.
Reactivity ProfileThe dinitrate, a heart drug, can detonate when dry, but is non explosive with 30% of water [J. Haz.. Mater., 1992, 32(1), 87]. The mononitrate would be expected to be less reactive.
Health HazardFire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.
Fire HazardFlammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.
Clinical UseVasodilator:
Treatment and prophylaxis of angina
Adjunct in congestive heart failure
Synthesis
Isosorbide

652-67-5

ISOSORBIDE 2-MONONITRATE

16106-20-0

The general procedure for the synthesis of isosorbide 2-nitrate from isosorbide (stored below +4°C) is as follows: 146 g of dehydrated sorbitol was dissolved in 880 mL of anhydrous ethyl acetate, stirred well, and then cooled to -5 to 0°C. Subsequently, 170 g of silver nitrate solids were added, stirring was continued, and 120 g of thionyl chloride was added dropwise at a slow rate. After the dropwise addition was completed, the reaction mixture was stirred at the same temperature for 10 hours. Upon completion of the reaction, the reaction process was monitored by high performance liquid chromatography (HPLC). The reaction solution was filtered by suction filtration. The filtrate was washed to neutrality with 500 mL of water to purify the product. The organic phase was dried with 20 g of anhydrous magnesium sulfate for 4 hours. After drying, the magnesium sulfate was removed by filtration and the filtrate was decolorized by adding 17.6 g of activated carbon and heated to reflux for 30 minutes. After the decolorization was completed, the activated carbon was removed by filtration and the filtrate was concentrated to dryness by decompression to give 170 g of isosorbide 2-nitrate solid. The purity of the product was 99.85% and the yield was 89.0% by HPLC analysis.

References[1] Patent: CN107011354, 2017, A. Location in patent: Paragraph 0042-0057
[2] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 12, p. 1809 - 1810
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 9, p. 793 - 795
[4] ChemMedChem, 2015, vol. 10, # 10, p. 1724 - 1732
Tag:Isosorbide 5-mononitrate(16051-77-7) Related Product Information
Isosorbide Isosorbide dinitrate ISOSORBIDE 2-MONONITRATE,ISOSORBIDE 2-MONONITRATE 99-101.0% Sodium hydride Sorbitol NIVITIN DEHYDROGENASE Prenyl acetate isosorbide-5-mononitrate-2-glucuronide ISOSORBIDE-13C6 DINITRATE Isosorbide 5-mononitrate