BROMOHEXINE Chemical Properties

Melting point:

238℃

Boiling point:

413.8±40.0 °C(Predicted)

Density 

1.57

storage temp. 

2-8°C(protect from light)

solubility 

DMSO: 75 mg/mL (199.40 mM);Ethanol: 75 mg/mL (199.40 mM)

pka

8.34±0.20(Predicted)

Water Solubility 

Water: Insoluble

Safety Information

Toxicity

Approx LD50 orally in rabbits: >10 g/kg (Boyd, Sheppard)

BROMOHEXINE Usage And Synthesis

Originator

Bisolvon,Boehringer Ingelheim,Switz.,1963

Uses

Expectorant; mucolytic.

Definition

ChEBI: A substituted aniline that is 2,4-dibromoaniline which is substituted at position 6 by a [cyclohexyl(methyl)amino]methyl group. It is used (as the monohydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive ough (i.e. a cough characterised by the production of sputum).

Manufacturing Process

In initial steps, 2-nitrobenzylbromide and cyclohexylmethylamine are reacted and that initial product reacted with hydrazine to give N-(2-aminobenzyl)-Nmethyl- cyclohexylamine.
A solution of 29.3 g of bromine in 50 cc of glacial acetic acid was slowly added dropwise to a solution of 159 g of N-(2-aminobenzyl)-N-methylcyclohexylamine, accompanied by stirring. The glacial acetic acid was decanted from the precipitate formed during the addition of the bromine solution, and the precipitate was thereafter shaken with 200 cc of 2N sodium hydroxide and 600cc of chloroform until all of the solids went into solution. The chloroform phase was allowed to separate from the aqueous phase. The chloroform phase was decanted, evaporated to dryness and the residue was dissolved in absolute ether. The resulting solution was found to be a solution of N-(2-amino-3,5-dibromobenzyl)-N-methyl-cyclohexylamine in ethanol. Upon introducing hydrogen chloride into this solution, the hydrochloride of N-(2- amino-3,5-dibromobenzyl)-N-methyl-cyclohexylamine precipitated out. It had a melting point of 232°-235°C (decomposition).

Therapeutic Function

Expectorant; Mucolytic

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