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87-33-2

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87-33-2 Usage

Chemical Properties

white to light yellow crystal powde

Originator

Isordil,Ives,US,1959

Uses

Different sources of media describe the Uses of 87-33-2 differently. You can refer to the following data:
1. Isosorbide dinitrate is also used in chronic cardiac insufficiency for preventing angina pectoris attacks. It is a long-lasting drug.
2. Antianginal;Nitric oxide (NO) donor

Manufacturing Process

An aqueous syrup of 1,4:3,6-dianhydro-D-glucitol is slowly added to a cooled mixture of HNO3 and H2SO4. After standing a few minutes the mixture is poured into cold water and the precipitated product is collected and recrystallized from ethanol.

Brand name

Dilatrate (Schwarz Pharma); Isordil (Biovail); Isordil (Wyeth); Sorbitrate (AstraZeneca).

General Description

A crystalline solid. May be toxic by ingestion. Used to make pharmaceuticals. Used as a heart drug.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Nitroalkanes, such as Isosorbide dinitrate, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water. This heart drug is detonable when dry, but non-explosive with 30% of water.

Health Hazard

Fire 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 Hazard

Flammable/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 Use

Vasodilator: Prophylaxis and treatment of angina Left ventricular failure

Safety Profile

Moderately toxic by ingestion, intraperitoneal, intramuscular, and subcutaneous routes. Experimental reproductive effects. Mutation data reported. A flammable solid. When heated to decomposition it emits toxic fumes of NOx. A coronary vasodilator. See also NITRATES.

Synthesis

Isosorbiddinitrate, 1,4:3,6-dianhydrosorbate-2,5-dinitrate (19.1.4), is synthesized by intermolecular dehydration of D-sorbite into isosorbide (19.1.3) using paratoluenesulfonic acid and subsequent nitration of the two hydroxyl groups by nitric acid.

Veterinary Drugs and Treatments

Isosorbide mononitrate (ISMN) and dinitrate (ISDN) are organic nitrates potentially useful as preload reducing agents in treating heart failure in small animals, however, research and clinical experience demonstrating clinical efficacy are lacking in dogs or cats. Limited research indicates that dogs may require much higher dosages of isosorbide dinitrate to achieve therapeutic effects than do humans. In humans, isosorbide nitrates are used for treating or preventing angina, treating esophageal spasm, and as an adjunctive treatment in CHF.

Drug interactions

Potentially hazardous interactions with other drugs Avanfil, sildenafil, tadalafil, vardenafil: hypotensive effect significantly enhanced - avoid concomitant use. Riociguat: avoid concomitant use due to risk of hypotension.

Metabolism

Isosorbide dinitrate undergoes extensive first-pass metabolism in the liver. It is taken up by smooth muscle cells of blood vessels and the nitrate group is cleaved to inorganic nitrite and then to nitric oxide. It is also rapidly metabolised in the liver to the major active metabolites isosorbide 2-mononitrate and isosorbide 5-mononitrate. Isosorbide mononitrate is metabolised to inactive metabolites, including isosorbide and isosorbide glucuronide. Only about 2% of isosorbide mononitrate is excreted unchanged in the urin

Check Digit Verification of cas no

The CAS Registry Mumber 87-33-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 87-33:
(4*8)+(3*7)+(2*3)+(1*3)=62
62 % 10 = 2
So 87-33-2 is a valid CAS Registry Number.
InChI:InChI=1/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

87-33-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name isosorbide dinitrate

1.2 Other means of identification

Product number -
Other names Isosorbide dinitrate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:87-33-2 SDS

87-33-2Synthetic route

Isosorbide
652-67-5

Isosorbide

isosorbide dinitrate
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
Isosorbide
652-67-5

Isosorbide

B

isosorbide-2-mononitrate
16051-77-7

isosorbide-2-mononitrate

C

isosorbide dinitrate
87-33-2

isosorbide dinitrate

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
isosorbide dinitrate
87-33-2

isosorbide dinitrate

isosorbide-2-mononitrate
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%
isosorbide dinitrate
87-33-2

isosorbide dinitrate

B

isosorbide-2-mononitrate
16051-77-7

isosorbide-2-mononitrate

C

Isosorbide
652-67-5

Isosorbide

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.;
isosorbide dinitrate
87-33-2

isosorbide dinitrate

isosorbide 2-O-butanoate
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
isosorbide dinitrate
87-33-2

isosorbide dinitrate

isosorbide 2-butyrate-5-mononitrate

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

87-33-2Upstream product

87-33-2Relevant articles and documents

METHOD FOR PREPARING NITRATE ESTER

-

Paragraph 0026-0030, (2020/05/29)

A method for preparing a nitrate ester is provided. The method includes providing a first solution including a compound (which has at least one hydroxyl group) and a carboxylic acid having 2-5 carbon atoms; providing a second solution including nitric acid, acetic anhydride, and acetic acid; and transferring the first solution and the second solution to a microreactor, obtaining a nitrate ester after a residence time. In particular, the ratio of the weight of nitric acid to the total volume of the acetic anhydride and acetic acid is 1:1 to 1:3.5. The ratio of the molar amount of nitric acid to the hydroxyl group equivalent of the compound is from 1:1 to 15:1.

Method for synthesizing 5-isosorbide mononitrate by aid of micro-channel reactors

-

Paragraph 0048-0078; 0095; 0097, (2018/10/19)

The invention belongs to the field of medicine synthesis, and particularly discloses a method for synthesizing 5-isosorbide mononitrate by the aid of micro-channel reactors. The method includes pumping nitrification reagents and isosorbide liquid into the micro-channel reactors and carrying out hybrid reaction; allowing products to flow out from outlets of the micro-channel reactors after the reaction is completely carried out; carrying out after-treatment on the products and separating and purifying the products to obtain the 5-isosorbide mononitrate which is a target product. The method hasthe advantages that the method is short in reaction time and is safe as compared with the traditional processes, and the yield of the 5-isosorbide mononitrate can be greatly increased.

A 5-isosorbide Mononitrate the synthesis and purification method

-

Paragraph 0045-0051, (2017/01/23)

The invention provides a method for synthesizing and purifying 5-isosorbide mononitrate. The method comprises the steps of: (1) preparing a nitrifying reagent from concentrated nitric acid, acetic acid and acetic anhydride, and directly nitrifying isosorbide to obtain an isosorbide nitride mixture; (2) adding water to arouse a quenching reaction, separating out 2,5-isoscrbide dinifrate at a temperature ranging from 0 to 5 DEG C, and filtering out the 2,5-isoscrbide dinifrate; (3) reacting the filtrate with sodium hydroxide to prepare an isosorbide mononitrate sodium salt aquo-complex, filtering, and hydrolyzing the sodium salt; and (4) extracting, concentrating and recrystallizing to obtain high-purity 5-isosorbide mononitrate. The preparation method provided by the invention is simple, safe, easy to operate and short in reaction period; impurities are easy to remove, and the yield and the purity are high; therefore, the method lays a foundation for industrial production.

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