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  • Title: N-monosubstituted urethanes and esters of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-5-trans-ol with hypotensive and other activities.
    Author: Bondavalli F, Ranise A, Schenone P, Ruggiero E, Berrino L, Giasi M, Marmo E.
    Journal: Farmaco Sci; 1983 May; 38(5):318-29. PubMed ID: 6862002.
    Abstract:
    The synthesis of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-trans-ol (III) starting from 1,3,3-trimethyl-6-nitrimino-2-oxabicyclo[2.2.2]octane is described. Starting from aminoalcohol (III), a series of N-substituted urethanes (IV) and esters (V), as well as the rigid analogue of acetylcholine (VII), were prepared. A number of compounds (V) and particularly (IV) showed remarkable hypotensive and bradycardic activities in rats, whereas the p-aminobenzoate (V h) showed infiltration anesthesia in mice comparable to that of lidocaine. Antiarrhythmic activity in mice and antiacetylcholine activity in vitro are also reported.
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