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OXITROPIUM BROMIDE

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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
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OXITROPIUM BROMIDE Chemical Properties

Melting point:
203-204° (dec)
alpha 
D21 -25° (c = 2.0 in water)
solubility 
Very soluble in water, freely soluble in methanol, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
form 
neat
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Safety Information

Toxicity
LD50 orl-rat: 2250 mg/kg DRFUD44,117,79
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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.

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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