Evidence for Metabolic a Hydroxylation of N-Nitrosopyrrolidine

Stephen S. Hecht, Chi Hong B. Chen, Dietrich Hoffmann

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Metabolic a hydroxylation of cyclic nitrosamines is important in the activation of these compounds to their ultimate carcinogenic forms. Direct evidence for this process is presented. Both α-hydroxynitrosopyrrolidine and 3-formyl-1-propanediazohydroxide, which are unstable intermediates resulting from a hydroxylation of nitrosopyr rolidine, were generated in aqueous solution from the stable precursors α-acetoxynitrosopyrrolidine and 4-(N-carbethoxy-N-nitrosamino)butanal. The major product resulting from the decomposition of α-hydroxynitrosopyrrolidine and 3-formyl-1-propanediazohydroxide was 2-hy-droxytetrahydrofuran, the cyclic hemiacetal of 4-hydroxy-butyraldehyde. The same product was isolated as its dinitrophenylhydrazone derivative after incubation of rat liver microsomes with nitrosopyrrolidine and after treatment of rats with nitrosopyrrolidine.

Original languageEnglish (US)
Pages (from-to)215-218
Number of pages4
JournalCancer Research
Issue number1
StatePublished - Jan 1978


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