The nitrous acid test for amines - A potentially hazardous reaction

In view of the known toxicological properties of nitrosamines with laboratory animals and the uncertainties concerning their danger toward humans, the...
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The Nitrous Acid Test for Amines-A

Potentially Hazardous Reaction

Most research laborataries in which nitrosamines are being investigated have consequently adopted stringent guidelines for the handling and dispasal of nitrosamines. These guidelines typically include the use of rubber gloves, specially designated hoods. and swciallv desienated balances durine anv mani~ulationsof nitrosamines even in dilute solution. desoite'the wihesoriad oublicitv eiven tonitrosamin; carcinoeenesis. includine a recent article in this Journal.' we results in high conversions to the corresponding nitrosamine. A number of organic laboratory manuals examined a t random, including one edition copyrighted in 1974, contained ~roeedureswhich could produce as much as 500 ma of nitrosamine per student if carried out with secondary amines. None bf the texts which we examined contained any indication that nitrosamines are toxic and potentially carcinogenic and none mentioned that special precautions should be observed when working with amines and nitrous acid. In view of the known toxieoloeical of nitrosamines with laboratom animals and the uncertainties coneernine .. ornnerties , their dsnyrr t w o n l human*, we Ire1 that the initructwe \.slue of t i l l r rcnrrm prubatdr clocs nur warrant i t cmt~nucrlwr. rrpcriall\ :n iituntiuna whtw s p w a l prrraurnms mnnot be cmplmrd. 118 ;~ddit~cm, we i d that d~siusswm< g l i n:trownm-r. partiwlrrly in inhorntory rnanunls, zhtmld include stnmgly u o n l d cautionary notes concerning the potential carcinogenicity of nitrosamines. ~

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'Barnes, J. M.,and Magee,P. N.,Brit. J. Indust. Med. 11,167 (1954);Magee.P. N.,Riorhem. J., 70,606 (19583: Shank, R. C., Tox. Appl Pharmnrol., 31,361 (1975). Wruckrey, H., Preussmann, R., and Ivankovic, S., Ann. N. Y Aeod Sci.,163,676 (1969); Magee, P. N., and Barnes, J. M.. Adu. C a n e e r R e s -10.163 ~~.~~ ~~~~. ~ . 11967). . .

:'Wogan, G. N., and Tannenhaum, S. R.,Tax. Appl. Pknrm., 31,375 (1975). ~

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Ferguson, L. N.,J. CHEM. EDUC., 52,688 (1975).

Massachusetts Institute of Technology Cambridge, 02139

J o h n S. Wishnok Michael C. Archer

Volume 53, Number 9. September 1976 / 559