Irreversible Adrenergic α-Receptor Antagonism by (R)- and (S)-N-(2-Chloroethyl)-N-methyl-2-phenyl-2-hydroxyethylamine and Related Agents

The synthesis of the title compounds is described from the corresponding mandelic acids. The compounds were significantly less effective than phenoxybenzamine as irreversible α-adrenergic receptor antagonists. The S isomer was moee effective than the R isomer by a factor of 6. Interpretation of these differences is complicated by the finding that these agents, in commnn with many other 2-halogenoethylamines, appear to produce their actions through at least two different sites of reaction.