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Basic Information
CAS No.: 16051-77-7
Name: Isosorbide 5-mononitrate
Article Data: 26
Molecular Structure:
Molecular Structure of 16051-77-7 (Isosorbide 5-mononitrate)
Formula: C6H9NO6
Molecular Weight: 191.141
Synonyms: Glucitol,1,4:3,6-dianhydro-, 5-nitrate, D- (8CI);BM 22-145;ConpinRetardkaps;Corangin SR;Duride;Elantan;ElantanLong;Elantan Retard;IS 5MN;Imdur;Imdur Durules;Imtrate;Ismo;Isomonit;Isopen 20;Isosorbidemononitrate;Iturol;Momo Mack;Monis;Monit 20;Mono-Cedocard;Mono-Mack;Monocord 20;Monoket Retard;Monolong 40;Mononit;Monopront;Monosorb;Monosordil;Monovas;Ormox;Pentacard;Vasotrate;
EINECS: 240-197-2
Density: 1.56 g/cm3
Melting Point: 88-93 °C
Boiling Point: 364.5 °C at 760 mmHg
Flash Point: 174.2 °C
Solubility: Soluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi,FlammableF
Risk Codes: 36/37/38-11
Safety: 37/39-16-15
Transport Information: UN 3251
PSA: 93.74000
LogP: -0.75500
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Specification

The IUPAC name of Isosorbide 5-nitrate is [(3S,3aR,6R,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]nitrate. With the CAS registry number 16051-77-7 and EINECS 240-197-2, it is also named as 1,4:3,6-Dianhydro-D-glucitol 5-nitrate. The product's categories are Chiral; Nitric Oxide Reagents; Various Metabolites and Impurities; Heterocycles; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; API's. It is white to light yellow crystal powder which acts by dilating the blood vessels so as to reduce the blood pressure. When heated to decomposition it emits toxic fumes of NOx.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.51; (4)ACD/LogD (pH 7.4): -0.51; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.53; (8)ACD/KOC (pH 7.4): 12.53; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 82.74 Å2; (13)Index of Refraction: 1.542; (14)Molar Refractivity: 38.44 cm3; (15)Molar Volume: 122 cm3; (16)Polarizability: 15.24×10-24 cm3; (17)Surface Tension: 60.2 dyne/cm; (18)Density: 1.56 g/cm3; (19)Flash Point: 174.2 °C; (20)Enthalpy of Vaporization: 70.68 kJ/mol; (21)Boiling Point: 364.5 °C at 760 mmHg; (22)Vapour Pressure: 8.66E-07 mmHg at 25°C.

Preparation of Isosorbide 5-nitrate: With sorbitol as raw materials, we can get anhydro sorbitol by dehydration cyclization. Then, after reacting with nitric acid and acetic anhydride at 10 ~ 15 °C for 2.5h, we can get the product.

Isosorbide 5-nitrate can be obtained by sorbitol

Uses of Isosorbide 5-nitrate: It is a nitrate-class drug used for the prophylactic treatment of angina pectoris. But this drug has side effects including headache and tiredness. It can react with benzoyl chloride to get benzoic acid 6-nitrooxy-hexahydro-furo[3,2-b]furan-3-yl ester. This reaction needs reagent Et3N and solvent CHCl3 at ambient temperature. The reaction time is 2 hours. The yield is 65%.

Isosorbide 5-nitrate can react with benzoyl chloride to get benzoic acid 6-nitrooxy-hexahydro-furo[3,2-b]furan-3-yl ester

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep it away from heat and sources of ignition. It is irritating to eyes, respiratory system and skin. If you want to contact this product, you must wear suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:[O-][N+](=O)O[C@H]1[C@H]2OC[C@H](O)[C@H]2OC1
2. InChI:InChI=1/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
3. InChIKey:YWXYYJSYQOXTPL-SLPGGIOYBW

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1810mg/kg (1810mg/kg) BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 29, Pg. 327, 1985.
mouse LD50 intravenous 1820mg/kg (1820mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 29, Pg. 327, 1985.
mouse LD50 oral 1771mg/kg (1771mg/kg)   Bollettino Chimico Farmaceutico. Vol. 128, Pg. 74, 1989.
rat LD50 intraperitoneal 1760mg/kg (1760mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 29, Pg. 327, 1985.
rat LD50 intravenous 1750mg/kg (1750mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 29, Pg. 327, 1985.
rat LD50 oral 2010mg/kg (2010mg/kg) BEHAVIORAL: ATAXIA

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Oyo Yakuri. Pharmacometrics. Vol. 29, Pg. 327, 1985.