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Journal of Pharmacology And Experimental Therapeutics, Vol. 150, Issue 2, 309-315, 1965
Copyright © 1965 by American Society for Pharmacology and Experimental Therapeutics

N-DEALKYLATION OF ANILERIDINE TO NORMEPERIDINE

Shih-Chia Chen Lin 1 and E. Leong Way 1

1 Department of Pharmacology, Schools of Medicine and Pharmacy, University of California, San Francisco, California

The metabolism of anileridine was investigated in male Sprague-Dawley rats. N-Dealkylation was established to be an important biotransformation pathway by identifying and isolating the dealkylation products of anileridine, namely normeperidine and p-aminophenylacetic acid as its acetyl conjugate from the urine of animals receiving anileridine.

Normeperidine was separated from the benzene extract of alkalinized urine, purified by paper chromatography and isolated as the picrate salt. Identification of normeperidine in the benzene extract was effected by paper and thinlayer chromatography, countercurrent distribution, ultraviolet and infrared absorption studies. Normeperidine was also identified in human, rabbit and guinea-pig urine by thin-layer chromatography.

p-Acetylaminophenylacetic acid was isolated from the concentrated ethyl acetate extract of acidified rat urine after purification by countercurrent distribution, and was identified by thinlayer chromatography. After hydrolysis of the product and subjecting it to countercurrent distribution, a distribution curve similar to authentic p-aminophenylacetic acid was obtained. The derived product also exhibited similar properties as the known compound on thin-layer silica gel plates.

Accepted on June 2, 1965






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Copyright © 1965 by the American Society for Pharmacology and Experimental Therapeutics.