Cyclizing compounds. 3. Local anesthetic action of N (ω haloalkyl) N methylaminoaceto 2,6 xylidides

Article abstract of DOI:10.1021/jm00265a010

A series of N (ω chloroalkyl) N methylaminoaceto 2,6 xylidides which are able to cyclize to quaternary ammonium derivates was synthesized and examined for local anesthetic action. As reference compounds the corresponding series of N alkylamine derivates were synthesized and tested. In both series of compounds the duration of anesthesia was prolonged by increasing the size of the side chain. In the N alkylamine series an optimal effect was obtained for the N hexylamine derivate. The duration of anesthesia produced by the cyclizing compounds in the sciatic nerve test in vivo was somewhat shorter than that for the noncyclizing compounds. The observation that the N 4 chlorobutyl derivate produced a longer block than the 5 chloropentylamine in this test indicates that the quaternary compounds formed may contribute to the duration of anesthesia.