Synthesis and adrenergic neuron blocking properties of some alkylating analogues of bretylium

A series of ortho-substituted N-alkyl-N-(2-chloroethyl)-benzylamines have been prepared. These compounds are structurally similar to the adrenergic neuron blocking agent bretylium. They were tested for neuron blocking activity using both the innervated rabbit jejunum and the vas-deferens-hypogastric nerve preparation of the guinea pig. Three compounds possessed some adrenergic neuron blocking activity of a prolonged nature, the most potent being N-(2-chloroethyl)-N-(0-bromobenzyl)-ethylamine.