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Microsomal metabolism of chlorinated ethylenes.

Authors
Leibman-KC; Ortiz-E
Source
Sixth International Congress on Pharmacology, July 20 - 25, 1975, Helsinki, Finland. Helsinki, Finland: Samonaprint, Abstract 608, 1975 Jul; :257
Link
NIOSHTIC No.
00071478
Abstract
Trichloroethylene (79016) has been shown to be converted to chloral- hydrate (75876) in the presence of liver microsomes, reduced nicotinamide adenine-dinucleotide-phosphate (53576) (NADPH), and oxygen. It was postulated that the reaction proceeded via epoxidation of the substrate, followed by rearrangement of the epoxide, with migration of a chlorine (7782505) atom, to yield chloral, or by a pinacol-type rearrangement of the diol formed from the epoxide by the action of epoxide-hydrase (9048639), with exchange of chlorine and hydroxyl groups, to yield chloral-hydrate. The metabolism of this and other chlorinated ethylenes in liver microsomes has now been further studied. Dichloroacetic-acid, which would be formed via dichloroacetyl-chloride by rearrangement of the epoxide with migration of a hydrogen atom rather than a chlorine- atom, could not be detected as a metabolite of trichloroethylene in liver microsomes. The NADPH-dependent formation of trichloroacetic- acid (76039) from tetrachloroethylene in rat liver microsomes has been demonstrated. Similarly, monochloroacetic-acid (79118) has been found to be a metabolite of 1,1-dichloroethylene (75354). Both of these products could arise, via the respective acyl-chlorides, by rearrangement of either epoxide or diol intermediates. No monochloroacetic-acid could be detected as a metabolite of trans-1,2- dichloroethylene; formation of monoacetyl-chloride would require migration of hydrogen, rather than chlorine, in rearrangement of 1,2- dichloroethylene (79367), which was identical in gas chromatographic behavior to an unidentified metabolite of 1,2-dichloroethylene. (Grant No. R01-OH-00316)
Keywords
NIOSH-Grant; Grants-other; Chlorinated-hydrocarbons; Organic-solvents; Biochemical-reactions
Contact
Pharmacology and Therapeutics Univ of Florida Coll of Med Dept of Pharma & Therapeutics Gainesville, Fla 32601
CAS No.
79-01-6; 75-87-6; 53-57-6; 7782-50-5; 9048-63-9; 76-03-9; 79-11-8; 75-35-4; 79-36-7
Publication Date
19750701
Document Type
Abstract
Funding Amount
460733
Funding Type
Grant
Fiscal Year
1975
NTIS Accession No.
NTIS Price
Identifying No.
Grant-Number-R01-OH-00316
Priority Area
Other Occupational Concerns; Grants-other
Source Name
Sixth International Congress on Pharmacology, July 20 - 25, 1975, Helsinki, Finland
State
FL
Performing Organization
University of Florida Gainesville, Gainesville, Florida
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