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The preparation of tritium labeled N-nitrosamines

✍ Scribed by W. Lijinsky

Publisher
John Wiley and Sons
Year
1966
Tongue
French
Weight
411 KB
Volume
2
Category
Article
ISSN
0022-2135

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✦ Synopsis

Dimethylnitrosamine, nitrosomorpholine, nitrosopyrrolidine, nitrosopiperidine, nitrosoazetidine, hexamethylenenitrosamine, nitrosornethylcyclohexylamine, nitrosomethylaniline and dinitrosopiperazine have been prepared labeled with tritium by nifrosation of the corresponding amines which had been labeled by exposure to tritium gas. The nitrosamines were purified by distillation in aqueous solution and by extraction with ether or chloroform. The specific activities varied,from 17 pclmg .for nitrosomorpholine to 540 pclmg ,for nitrosomethylaniline.

[NTRODUCTION In order to study the interaction of N-nitrosamines with various constituents of the cell, including nucleic acids and proteins, it was necessary to obtain these compounds radioactively labeled. The difficulty in preparing the more complex of these compounds labeled with carbon-14 led to consideration of the much easier and cheaper labeling with tritium. Because of the risk of partial reduction of the nitrosamine by exposure to tritium gas in the Wilzbach procedure ( l ) , it was decided to label the amine by exposure to tritium gas and to prepare the labeled nitrosamine from the base. The first such preparation made, that of dimethylnitrosamine (2), was successful and the product had fairly high specific activity. Furthermore, it was shown in the biochemical experiments carried out with this material that the labeling was as satisfactory as with carbon-14; that is, there was little or no tendency for the tritium atoms attached to carbon atoms to exchange with hydrogen in solution.

Consequently, a series of bases (purified by fractional distillation using a high efficiency column) were labeled with tritium by exposure for 2 weeks to

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