Esters and N-substituted urethanes of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-cis-ol with hypotensive and other activities.

The synthesis of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-cis-ol (III) starting from 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-trans-ol (I) is described. Starting from aminoalcohol (II), a series of esters (IV) and N-substituted urethanes (V) was prepared. Benzoate (IV e) showed a remarkable hypotensive and bradycardic activity in rats, whereas acetate (IV a) showed infiltration anesthesia and antiarrhythmic activity in mice slightly inferior to those of lidocaine. Antiacetylcholine activity in vitro is also reported.