OXITROPIUM BROMIDE
OXITROPIUM BROMIDE Basic information
- Product Name:
- OXITROPIUM BROMIDE
- Synonyms:
-
- (-)-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
- Oxivent
- Scopolamine ethobromide
- Tersigan
- CAS:
- 30286-75-0
- MF:
- C19H26BrNO4
- MW:
- 412.32
- EINECS:
- 250-113-6
- Mol File:
- 30286-75-0.mol
OXITROPIUM BROMIDE Chemical Properties
- Melting point:
- 203-204° (dec)
- alpha
- D21 -25° (c = 2.0 in water)
- 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.
- color
- Off-White to Pale Yellow
- Stability:
- Hygroscopic
OXITROPIUM BROMIDE Usage And Synthesis
Description
Oxitropium bromide is an analog of the anticholinergics methscopolamine bromide and ipratropium bromide, useful in the treatment of bronchial asthma. Cited advantages include a long duration of action and lack of cardiovascular effects.
Chemical Properties
White or almost white, crystalline powder.
Originator
Boehringer Ingelheim (W. Germany)
Uses
Anticholinergic; treatment of reversible airways obstruction.
Uses
Oxitropium Bromide is an anticholinergic agent.
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.
brand name
Oxivent (Boehringer Ingelheim);TERSIGAT.
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.
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