30286-75-0

Basic information

• Product Name: OXITROPIUM BROMIDE
• Synonyms: OXITROPIUM BROMIDE;(-)-n-ethyl-norhyoscine-methobromide;3-oxa-9-azoniatricyclo(3.3.1.0(sup2,4))nonane,9-ethyl-7-(3-hydroxy-1-oxo-2-ph;ba253br;ba-253-br-l;bromurodeoxitropio;enylpropoxy)-9-methyl-,bromide,(7(s)-(1-alpha,2-beta,4-beta,5-alpha,7-beta));n-ethyl-norscopolaminemethobromide
• CAS NO: 30286-75-0
• Molecular Formula: Br*C₁₉H₂₆NO₄
• Molecular Weight: 412.32
• EINECS: 250-113-6
• Mol File: 30286-75-0.mol

Chemical Properties

• Melting Point: 203-204° (dec)
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Very soluble in water, freely soluble in methanol, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
• CAS DataBase Reference: OXITROPIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: OXITROPIUM BROMIDE(30286-75-0)
• EPA Substance Registry System: OXITROPIUM BROMIDE(30286-75-0)

Safety Data

• Hazardous Substances Data: 30286-75-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Oxitropium bromide is used as an anticholinergic agent for the treatment of reversible airways obstruction. It helps in managing bronchial asthma by reducing the symptoms and improving the patient's breathing capacity.
Used in Respiratory Medicine:
Oxitropium bromide is used as a bronchodilator for the treatment of bronchial asthma. Its long-lasting action and minimal cardiovascular side effects make it a preferred choice for patients suffering from respiratory disorders.
Brand Names:
Oxivent (Boehringer Ingelheim) and TERSIGAT are some of the brand names under which OXITROPIUM BROMIDE is marketed.

Originator

Boehringer Ingelheim (W. Germany)

Manufacturing Process

14.5 g (0.05 mol) of (-)-norscopolamine and 5.4 g (0.05 mol) of ethyl bromide were dissolved in 300 cc of acetonitrile, 5.3 g (0.05 mol) of anhydrous sodium carbonate were suspended in the solution, and the suspension was heated at the boiling point for 10 hours. After a boiling time of 2.5 and 5 hours, respectively, the supply of ethyl bromide and sodium carbonate in the reaction mixture was replenished by adding each time 5.4 g (0.05 mol) of ethyl bromide and 5.3 g (0.05 mol) of anhydrous sodium carbonate. At the end of 10 hours of boiling, the inorganic sodium salts which had separated out were separated by vacuum filtration, the filter cake was washed with acetonitrile, and the acetonitrile was distilled out of the filtrate. The distillation residue was dissolved in ether, the solution was extracted with a small amount of water and then dried, and the ether was distilled off, yielding raw (-)-N-ethylnorscopolamine. 7.0 g (0.022 mol) of (-)-N-ethylnorscopolamine were dissolved in acetonitrile, 10.4 g (0.11 mol) of methyl bromide were added to the solution, and the mixture was allowed to stand at room temperature. The crystalline precipitate formed thereby was collected and recrystallized from acetonitrile.8.9 g (97.8% of theory) of white crystalline (-)-N-ethylnorscopolamine methobromide, melting point 203°C to 204°C (decomposition), were obtained.

Therapeutic Function

Anticholinergic bronchodilator

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and subcutaneous routes. An anticholinergic bronchodilator. When heated to decomposition it emits very toxic fumes of NOx and Brí.

InChI:InChI=1/C19H26NO4.BrH/c1-3-20(2)15-9-13(10-16(20)18-17(15)24-18)23-19(22)14(11-21)12-7-5-4-6-8-12;/h4-8,13-18,21H,3,9-11H2,1-2H3;1H/q+1;/p-1/t13?,14-,15-,16-,17-,18+,20?;/m1./s1

Upstream product

• 74-83-9 methyl bromide 
• 67009-40-9 (-)-N-Ethylnorscopolamin 
• 74-96-4 ethyl bromide 
• 24676-80-0 (-)-Norscopolamin-hydrochlorid 
• 114-49-8 hyoscine hydrobromide 

Downstream Products

• 67009-40-9 (-)-N-Ethylnorscopolamin 
• 51-34-3 scopolamine 

Relevant articles and documents

Pharmaceutical composition using a mixture of propellant gases for a metered dose inhaler

New advantageous propellent gas mixtures contain two or more components, at least one of which is a partially fluorinated lower alkane, and may be used in pharmaceutical preparations.

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Pharmaceutical preparations for producing powder aerosols using propellant gases which use TG 227, and possibly also TG 11, TG 12, TGH 114, propane, butane, pentane or DME.

The synthesis of anticholinergically active N-alkylnorscopolamines and their quaternary salts with particular consideration of the bronchospasmolytic compound (-)-N-ethylnorscopolamine methobromide (Ba 253 BR)

The synthesis of anticholinergic N-alkylnorscopolamines and their quaternary salts, especially the synthesis of (-)-N-ethylnorscopolamine methobromide (Ba 253 BR), is reported. (-)-N-Ethylnorscopolamine methobromide differs from the stereoisomeric (-)-N-ethylscopolammonium bromide not only by its physico-chemical, but also by its pharmacological properties. (-)-N-Ethylnorscopolamine methobromide represents an anticholinergic bronchodilator with long duration of action.