Butethamine Property

Boiling point:

378.78°C (rough estimate)

Density 

1.0604 (rough estimate)

refractive index 

1.5430 (estimate)

Hazard and Precautionary Statements (GHS)

Butethamine Chemical Properties,Usage,Production

Originator

Monoceine,Novocol,US,1941

Definition

ChEBI: Butethamine is a benzoate ester.

Manufacturing Process

The preparation of the normal butyl analog is as follows:
10 g of isobutylaminoethanol, 16 g of p-nitrobenzoyl chloride and 5 g of sodium hydroxide in 175 cc of water were allowed to react. The temperature was maintained between 30°-40°C during reaction. The reaction mixture was extracted with ether, the ether evaporated, and the resultant oil washed with water to remove any unreacted secondary amino alcohol and then dried. The yield was 21 g or 91% of theory. The compound responded positively when tested for the presence of the amine configuration and also the nitro group. The yellow viscous oil which was formed was isobutylaminoethyl p-nitrobenzoate. 20 g of this latter material was directly reduced with 15 g of tin and 50 cc of concentrated hydrochloric acid. The temperature of the reduction was controlled by addition from time to time of small quantities of cold water to maintain the temperature at or near 70°C. When the reaction was completed 150 cc of sodium hydroxide was added and the solution then cooled to 15°C. The oil which gradually formed combined with undissolved tin to form a pasty mass which soon settled. The supernatant liquid was decanted and the residue washed two or three times with water to remove all traces of alkali. The oily mass, freed from most of its water, was then extracted with ether and filtered. The filtrate was evaporated to dryness and the yield of the base obtained was 13 g or 73.5% of theory. In order to get the melting point of the base, the monohydrochloride was first formed and purified, then the hydrochloride was dissolved in water and just neutralized with ammonia water. The colorless oil formed soon crystallized into a white solid, which after filtration and air drying, had a melting point of 74°-74.5°C. The hydrochloride was made when the oily base was dissolved in propyl alcohol and the calculated quantity of aqueous hydrochloric acid added to form the monohydrochloride of this compound. After repeated recrystallizations, a white needle crystal was formed which had a melting point at 146°C.

Therapeutic Function

Local anesthetic