22131-35-7

Surheme,Aron,France,1969

Butalamine is a vasodilator (peripheral) with local anesthetic effects. Butalamine has been shown to inhibit state 3 respiration and decrease ADP/O in rat liver.

ChEBI: Butalamine is an oxadiazole and a ring assembly.

Benzaldehyde and hydroxylamine may be reacted, the product chlorinated and then reacted with cyanamide to give 5-amino-3-phenyl-1,2,4-oxadiazole.
32 grams of 3-phenyl-5-amino-1,2,4-oxadiazole dissolved in about 150 ml of anhydrous benzene, 7.8 grams of sodium amide are added and the reaction mixture heated at the boiling point with stirring for 2 hours. A solution of 38.3 grams of dibutylaminoethyl chloride in benzene is then added and the mixture heated to boiling under reflux for four hours. The sodium chloride is separated as previously described, the benzene removed by vacuum distillation and 56 grams of 3-phenyl-5-(dibutylaminoethylamino)-1,2,4-oxadiazole is obtained in the form of an oil which is then converted directly to the crystalline hydrochloride. This is accomplished by dissolving the oil in ethanol and adding the stoichiometric equivalent of anhydrous ethyl ether saturated with gaseous hydrogen chloride. The recrystallized salt is found to have a melting point of 145°C.

Vasodilator