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Chemical Compound Review:

Picrite 2-nitroguanidine

Synonyms: Nitroguanidine, WLN: WNMYZUM, ARONIS24123, AGN-PC-00FRXM, ACMC-1AUQS, ...

Dick, R.A. et al., Ho, B. et al., Niles, J.C. et al., Gupta, R.K. et al., Heitholt, J.J. et al.

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Disease relevance of Picrite

Toxicity and uptake of nitroguanidine in plants [1].

High impact information on Picrite

It is both oxidatively metabolized by cytochrome P450 enzymes and reduced at the nitroguanidine moiety by a previously unidentified cytosolic "neonicotinoid nitroreductase", the subject of this investigation [2].
Upon base hydrolysis, IV releases nitroguanidine (IVa) and an intermediate, 1-(2,3, 5-tri-O-acetyl-beta-D-erythro-pentofuranosyl)-5-iminoimidazolidine -2, 4-dione (IVb) [3].
Mutagenic potential of nitroguanidine and nitrosoguanidine in the Drosophila melanogaster sex-linked recessive lethal assay [4].

Biological context of Picrite

Nitroguanidine is a chemical of low toxicity (LD50 greater than 5 g/kg); it is quantitatively absorbed from the gastrointestinal tract, distributed throughout the body, and rapidly excreted in the urine [5].

References

Toxicity and uptake of nitroguanidine in plants. Heitholt, J.J., Hodgson, R.H., Tworkoski, T.J. Bulletin of environmental contamination and toxicology. (1990) [Pubmed]
Identification of aldehyde oxidase as the neonicotinoid nitroreductase. Dick, R.A., Kanne, D.B., Casida, J.E. Chem. Res. Toxicol. (2005) [Pubmed]
A novel nitration product formed during the reaction of peroxynitrite with 2',3',5'-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-nitro-N'-[1-(2,3,5-tri-O-acetyl-beta-D-erythro-pentofuranosyl)- 2, 4-dioxoimidazolidin-5-ylidene]guanidine. Niles, J.C., Wishnok, J.S., Tannenbaum, S.R. Chem. Res. Toxicol. (2000) [Pubmed]
Mutagenic potential of nitroguanidine and nitrosoguanidine in the Drosophila melanogaster sex-linked recessive lethal assay. Gupta, R.K., Korte, D.W., Reddy, G. Journal of applied toxicology : JAT. (1993) [Pubmed]
The fate of nitroguanidine in the rat. Ho, B., Tillotson, J.A., Kincannon, L.C., Simboli, P.B., Korte, D.W. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1988) [Pubmed]

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