Alkylation of nucleic acids by N-nitrosodi-n-propyl-amine: evidence that carbonium ions are not significantly involved.
Administration of N-nitrosodi-n-propylamine to rats leads to the formation of 7-n-propylguanine but not 7-isopropylguanine in hepatic DNA. For RNA, a small amount of the rearranged adduct is formed. Alkylation of DNA and RNA therefore appears to occur primarily via a bimolecular reaction rather than a unimolecular pathway involving free alkyl cations.
D000478:Alkylation; D000818:Animals; D001711:Biotransformation; D002414:Cations, Monovalent; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000378:metabolism*; D006147:Guanine / Q000031:analogs & derivatives / Q000378:metabolism; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D008297:Male; D009602:Nitrosamines / Q000378:metabolism / Q000494:pharmacology*; D011437:Propylamines / Q000494:pharmacology; D012313:RNA / Q000378:metabolism*; D051381:Rats
D002414:Cations, Monovalent; D009602:Nitrosamines; D011437:Propylamines; C013161:N-nitroso(di-n-propyl)amine; C024069:7-n-propylguanine; C024047:7-isopropylguanine; D006147:Guanine; D012313:RNA; D004247:DNA