The metabolism of the soil fumigant 1,2-dibromo-3-chloropropane in the rat
- 1 November 1979
- journal article
- Published by Springer Nature in Cellular and Molecular Life Sciences
- Vol. 35 (11) , 1432-1434
- https://doi.org/10.1007/bf01962767
Abstract
The soil fumigant 1,2-dibromo-3-chloropropane (I) undergoes hydrolysis in the rat to a series of epoxide metabolites. Alkylation of glutathione by these epoxides produces 2 urinary metabolites identified as the mercapturic acids VI (R=COCH3) and VII (R=COCH3). Hydrolysis of the epoxides produces the male antifertility agentsa-chlorohydrin (IX, X=Cl) anda-bromohydrin (IX, X=Br) which are oxidatively metabolized to oxalic acid (XII), thus causing renal damage. These metabolic pathways can explain the toxic nature of the fumigant as a carcinogen, a male chemosterilant and as an agent causing kidney damage.Keywords
This publication has 17 references indexed in Scilit:
- The antifertility actions of α-chlorohydrin in the maleLife Sciences, 1978
- The Oxidative Metabolism of α-Chlorohydrin in the Male Rat and the Formation of SpermatocoelesXenobiotica, 1978
- Residues of dibromochloropropane in root crops grown in fumigated soilJournal of Agricultural and Food Chemistry, 1977
- A direct effect of α-chlorohydrin on motility and metabolism of ejaculated human spermatozoaContraception, 1975
- The Metabolism of 3-Chloro-, 3-Bromo- and 3-Iodopropan-1,2-diol in Rats and MiceXenobiotica, 1975
- EFFECTS OF -CHLOROHYDRIN AND RELATED COMPOUNDS ON THE REPRODUCTIVE ORGANS AND FERTILITY OF THE MALE RATReproduction, 1974
- Some observations on the source of cysteine for mercapturic acid formationBiochemical Pharmacology, 1969
- Toxicologic investigations of 1,2-dibromo-3-chloropropaneToxicology and Applied Pharmacology, 1961
- A Comparison of the Effects of Radiation and Radiomimetic Chemicals on the BloodBritish Journal of Haematology, 1955
- Bromide determination in body fluidsBiochemical Journal, 1953