Recognition of novel artifacts produced during the microsomal incubation of secondary alicyclic amines in the presence of cyanide

1. During the in vitro microsomal metabolism of the secondary alicyclic amines, nornicotine, anabasine or 4-benzylpiperidine in the presence of cyanide, a new product was formed. 2. Comparison of these new products with authentic compounds by hplc and ms showed they were the corresponding 1'-N-cyanomethyl compounds. 3. The source of the methylene group was shown to be formaldehyde, arising during incubation, from either microsomal lipid and/or glycerol used to store microsomes for long periods at low temperature. 4. The formation of the 1'-N-cyanomethyl compounds was enhanced in the presence of substrates producing formaldehyde during their metabolism, in direct relationship to the amount of formaldehyde generated. 5. The results indicate that care should be taken in interpreting data obtained from incubates containing secondary amines and cyanide, especially in the presence of substrates capable of donating formaldehyde.