Toxicity and metabolism of nitroalkanes and substituted nitroalkanes

Authors: Smith, David; Anderson, Robin

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 1/7/2013
Publication Date: 1/8/2013
Citation: Smith, D.J., Anderson, R.C. 2013. Toxicity and metabolism of nitroalkanes and substituted nitroalkanes. Journal of Agricultural and Food Chemistry. 61:763-779.

Interpretive Summary: Nitrogen containing compounds are common in nature and are vital to life. However, certain varieties of nitrogen-containing compounds, specifically those containing "nitro" groups are not common in nature, although a few do occur. Man-made nitro containing compounds are numerous and are used in products as diverse as agrochemicals, cosmetics, inks, and solvents. New varieties of nitro compounds have recently been discovered that reduced methane production by certain classes of bacteria. Naturally occurring nitro-containing compounds are found in a few plant species and may be toxic to grazing livestock. The purpose of this article is to review the differing toxicities of naturally-occurring and man-made nitro compounds and to review how the metabolism of each nitro compound contributes to the initiating events that occur during toxicity. The review shows that toxicities to nitro compounds are not easily generalized and that specific nitro compounds are toxic because of unique patterns of metabolism.

Technical Abstract: A series of low molecular weight nitro- containing compounds has recently been discovered to have a variety of biological activities including the reduction of anaerobic methane production in ruminant animals and activity against economically important human pathogens, including Salmonella sp. and shigella-toxin producing Escherichia coli. Although some of these nitrocompounds, nitroethane and 2-nitropropane for example, have been industrial chemicals and synthetic intermediates for years, others such as carboxymethyl nitro-amino acid analogs are new to science and have not been previously described. The purpose of this communication is to review the toxicological profiles, especially as related to events occurring during metabolism and biotransformation, which contribute to toxicological endpoints of established nitro aliphatic compounds. It is hoped that by summarizing existing knowledge, an understanding of the activities and toxicological profiles of newly established nitrocompounds might be anticipated or adverse events associated with their use might be avoided.