PT  - JOURNAL ARTICLE
AU  - H Tachizawa
AU  - T L MacDonald
AU  - R A Neal
TI  - Rat liver microsomal metabolism of propyl halides.
DP  - 1982 Nov 01
TA  - Molecular Pharmacology
PG  - 745--751
VI  - 22
IP  - 3
4099  - http://molpharm.aspetjournals.org/content/22/3/745.short
4100  - http://molpharm.aspetjournals.org/content/22/3/745.full
SO  - Mol Pharmacol1982 Nov 01; 22
AB  - The in vitro metabolism of 1-propyl halides (chloride, bromide, and iodide) by hepatic microsomes from phenobarbital-induced rats was examined. The following metabolites were detected: propene, 1,2-epoxypropane, 1,2-propanediol, propionic acid, and undefined species bound to protein (for propyl chloride). The addition of exogenous glutathione to the incubation mixture led to the production of S-(1'-propyl)glutathione and S-(2'-hydroxy-1'-propyl)glutathione. The ratio of the metabolites resulting from C1-C2 functionalization [propene, 1,2-propanediol, and S-(2'-hydroxy-1'-propyl)glutathione] to that resulting from C1 functionalization (propionic acid) increased as the halide progressed down the halide order chloride bromide, and iodide. Mechanisms which rationalize the distribution of propyl halide metabolites as a function of the halide are discussed. The preferred mechanism interprets that the results obtained are a consequence of the partitioning of the initial metabolic transformation between alpha-hydroxylation and halogen oxygenation pathways.