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Isosorbide dinitrate

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Name

Isosorbide dinitrate

EINECS 201-740-9
CAS No. 87-33-2 Density 1.65 g/cm3
PSA 128.56000 LogP -0.01580
Solubility Soluble in chloroform, acetone, slightly soluble in ethanol, water Melting Point 700 °C
Formula C6H8N2O8 Boiling Point 365.9 °C at 760 mmHg
Molecular Weight 236.14 Flash Point 186.6 °C
Transport Information UN 2907 Appearance White crystalline powder
Safety 36 Risk Codes 5-22
Molecular Structure Molecular Structure of 87-33-2 (Isosorbide dinitrate) Hazard Symbols HarmfulXn
Synonyms

Isdin;1,4:3,6-Dianhydrosorbitol-2,5-dinitrate;Glentonin-retard;Dinitro sorbide;Sorbidi nitrate;Isostenase;Cardio;Isomack;Duranitrat;Disorlon;Isordil Tembids;Sorbide T.D.;Dignionitrat;Dinitroisosorbide;Coronex;Cedocard;Isordil (TN);(2-Nitrooxy-4,8-dioxabicyclo[3.3.0]oct-6-yl) nitrate;SDM No. 40;Dilatrate SR;Isoket retard 40;Sorquat;Glucitol, 1,4:3,6-dianhydro-, dinitrate, D-;Dianhydrosorbitol 2,5-dinitrate;Vascardin;Tinidil;EureCor;TYB 3215;Angidil;Isorbid;Sorate-5;Isordil;Dinitrosorbide;Sorbislo;D-Glucitol,1,4:3,6-dianhydro-,dinitrate;Frandol;Isodinit;

 

Isosorbide dinitrate Synthetic route

652-67-5

Isosorbide

87-33-2

isosorbide dinitrate

Conditions
ConditionsYield
With nitric acid; acetic anhydride In acetic acid at 5 - 10℃; for 2h;92%
With nitric acid In acetic anhydride; acetic acid at 5 - 10℃; for 2h; Nitration;92%
With sulfuric acid; nitric acid
With nitric acid; acetic anhydride; acetic acid at 20℃; for 0.0194444h; Flow reactor;92 %Chromat.
Conditions
ConditionsYield
Stage #1: Isosorbide With nitric acid; acetic anhydride; acetic acid at 0 - 12℃; for 6h;
Stage #2: With sodium hydroxide at -5℃; for 1h; pH=13; Temperature;
A 41.53%
B n/a
Conditions
ConditionsYield
With nitric acid; acetic anhydride
With nitric acid; acetic anhydride In 2-methyltetrahydrofuran; acetic acid at -10℃; for 0.0105556h; Temperature; Solvent; Flow reactor; Overall yield = 65.5 %;A 214.2 g
B n/a
C n/a
With nitric acid; acetic anhydride In 2-methyltetrahydrofuran; acetic acid at -10℃; for 0.0105556h; Temperature; Solvent; Flow reactor; Overall yield = 49.4 %;A 161.5 g
B n/a
C n/a
Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol; water at 0℃; under 2250.23 Torr; for 12h; Autoclave;A 81.55%
B 16.1%
Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; diethylamine In ethanol; water at 0℃; under 2250.23 Torr; for 12h; Catalytic behavior; Temperature; Pressure; Reagent/catalyst; Autoclave;78.11%
With benzyltriethylammonium tetrathiomolybdate In N,N-dimethyl-formamide at 20℃; for 30h; Hydrolysis;70%
With titanium(IV) dichlorodiisopropylate; Benzyltriethylammonium borohydride In dichloromethane at -78 - 0℃; for 2h;57%
Multi-step reaction with 4 steps
1: NaBH4; cobalt phthalocyanine / methanol / 0.17 h
2: 62 percent / Subtilisin Carlsberg / tetrahydrofuran / 26 h
4: Na2CO3 / methanol
View Scheme
87-33-2

isosorbide dinitrate

16051-77-7

isosorbide-2-mononitrate

Conditions
ConditionsYield
With Benzyltriethylammonium borohydride; titanium tetrachloride In dichloromethane at -78 - 0℃; for 2h;71%
With iron(II) sulfate; water In methanol at 20℃; Reflux;69.65%
Conditions
ConditionsYield
With sodium tetrahydroborate; cobalt(II) phthalocyanine In methanol for 0.166667h; Reduction;A 52%
B n/a
C n/a
Conditions
ConditionsYield
metabolism study in patients with coronary heart desease after dosage of 80 mg p.o.;
87-33-2

isosorbide dinitrate

84207-83-0

isosorbide 2-O-butanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4; cobalt phthalocyanine / methanol / 0.17 h
2: 62 percent / Subtilisin Carlsberg / tetrahydrofuran / 26 h
View Scheme
87-33-2

isosorbide dinitrate

isosorbide 2-butyrate-5-mononitrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBH4; cobalt phthalocyanine / methanol / 0.17 h
2: 62 percent / Subtilisin Carlsberg / tetrahydrofuran / 26 h
View Scheme

Isosorbide dinitrate Consensus Reports

Reported in EPA TSCA Inventory.

Isosorbide dinitrate Standards and Recommendations

DOT Classification:  4.1; Label: Flammable Solid

Isosorbide dinitrate Specification

The Cardis with CAS registry number of 87-33-2 is also known as (3R,3aS,6S,6aS)-Hexahydrofuro[3,2-b]furan-3,6-diyl dinitrate. The IUPAC name is [(3S,3aS,6R,6aS)-3-Nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate. It belongs to product categories of Chiral; Nitric Oxide Reagents; Intermediates & Fine Chemicals; Pharmaceuticalsr. Its EINECS registry number is 201-740-9. In addition, the formula is C6H8N2O8 and the molecular weight is 236.14. This chemcial is a white crystalline powder and is obtained from sorbitol solution by cyclization and esterification.

Physical properties about Cardis are: (1)ACD/LogP: 0.90; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 0.9; (4)ACD/LogD (pH 7.4): 0.9; (5)ACD/BCF (pH 5.5): 2.85; (6)ACD/BCF (pH 7.4): 2.85; (7)ACD/KOC (pH 5.5): 73.73; (8)ACD/KOC (pH 7.4): 73.73; (9)#H bond acceptors: 10; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.537; (12)Molar Refractivity: 44.69 cm3; (13)Molar Volume: 142.9 cm3; (14)Surface Tension: 62.6 dyne/cm; (15)Density: 1.65 g/cm3; (16)Flash Point: 186.6 °C; (17)Enthalpy of Vaporization: 58.82 kJ/mol; (18)Boiling Point: 365.9 °C at 760 mmHg; (19)Vapour Pressure: 3.19E-05 mmHg at 25 °C.

Uses of Cardis: it is a nitrate used pharmacologically as a vasodilator such as in angina pectoris but also for anal fissure. Besides, it is also used as a direct vasodilator to treat congestive heart failure.

When you are using this chemical, please be cautious about it. As a chemical, it is harmful if swallowed. When heated, it may cause an explosion. During using it, wear suitable protective clothing.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O[N+](=O)[O-]
2. Isomeric SMILES: C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O[N+](=O)[O-])O[N+](=O)[O-]
3. InChI: InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
4. InChIKey: MOYKHGMNXAOIAT-JGWLITMVSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 1109mg/kg (1109mg/kg)   French Demande Patent Document. Vol. #2454807,
man TDLo oral 1714ug/kg/3D- (1.714mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Australian and New Zealand Journal of Medicine. Vol. 27, Pg. 596, 1997.
mouse LD50 intramuscular 1080mg/kg (1080mg/kg)   Drugs in Japan Vol. 6, Pg. 72, 1982.
mouse LD50 intraperitoneal 720mg/kg (720mg/kg)   Yakkyoku. Pharmacy. Vol. 24, Pg. 431, 1973.
mouse LD50 intravenous > 40mg/kg (40mg/kg) BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 4947, 1985.
mouse LD50 oral 1050mg/kg (1050mg/kg)   Drugs in Japan Vol. 6, Pg. 72, 1982.
mouse LD50 subcutaneous 1050mg/kg (1050mg/kg)   Drugs in Japan Vol. 6, Pg. 72, 1982.
rabbit LD50 intravenous > 40mg/kg (40mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 4947, 1985.
rat LD50 intramuscular > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. 6, Pg. 72, 1982.
rat LD50 intraperitoneal 670mg/kg (670mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 35, Pg. 287, 1988.
rat LD50 intravenous > 40mg/kg (40mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 4947, 1985.
rat LD50 oral 747mg/kg (747mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 309, 1984.
rat LD50 skin > 3gm/kg (3000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 35, Pg. 287, 1988.
rat LD50 subcutaneous 1237mg/kg (1237mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 2109, 1982.
women TDLo oral 100ug/kg (0.1mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE

CARDIAC: OTHER CHANGES
Southern Medical Journal. Vol. 84, Pg. 369, 1991.

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