Hydrazine carcinogenicity

Semicarbazide hydrochloride (hydrazine carboxamide hydrochloride) [563-41-7] M 111.5, m 173 (dec), 175 (dec), pK " 3.66. Crystd from aqueous 75% EtOH and dried under vacuum over CaS04. Also crystd from a mixture of 3.6 mole % MeOH and 6.4 mole % of water. [Kovach et al. J Am Chem Soc 107 7360 1985.] IR v 700, 3500 cm" [Org Synth Coll Vol I 485 I94I-, Davison and Christie J Chem Soc 3389 I955 -, Thiele and Stange Chem Ber 27 33 I894 pK Bartlett J Am Chem Soc 54 2853 1923]. The free base crystd as prisms from abs EtOH, m 96° [ Curtius and Heidenreich Chem Ber 21 55 1894]. TOXIC ORALLY, possible CARCINOGEN and TERATOGEN. 

Uses It is one active ingredient present in water which has been purified by chlorination (Ref 6). It is used as an intermediate for.the prepn of hydrazine and substituted hydrazines. Recentiy there has been a renewed interest in chloramine as a possible intermediate for the prepn of UDMH (see Vol 7, H203-R) which avoids handling the highly carcinogenic dimethyl-nitrosamine (Refs 5 7)... 

Despite the potential carcinogenic nature of hydrazine, it is still widely employed as an oxygen scavenger and is effective at higher temper-... 

Parodi, S., S.DeFlora, M.Cavanna, and others. 1981. DNA-damaging activity in vivo and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity. Cancer Res. 41 1469-1482. 

Carcinogenic compounds, 9 448 aromatic amine, 9 450 in dye production, 9 296 Carcinogenic elements, in ferrites, 11 59 Carcinogenicity. See also Cancer of acetaldehyde, 25 561 classification scheme for, 13 311 of herbicides, 13 311 hydrazine, 13 590-591 methanol, 16 314 of propylene oxide, 20 811 testing, 25 221-223 of 2,4-D, 13 315 Carcinogenic potential, 25 222 Carcinogenic risk, of nickel compounds, 17 120... 

Amides that undergo N-hydroxylation are often amides of arylamines (Fig. 4.87) some of which are carcinogens such as 2-acetylaminofluorene (Fig. 4.87). Initial N-hydroxylation of a hydrazine is similar to that of an amine however, further oxidation can lead to the formation of nitrogen gas and reactive species. The two-electron oxidation pathway is shown in Figure 4.87. Hydrazines also undergo one-electron oxidations but the intermediates are short-lived and these pathways are less well defined (154). 

I ARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans, Vol 71, Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide, pp 453-77. Lyon, International Agency for Research on Cancer, 1999... 

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