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Metabolites of Lindane

Metabolites: Any substances produced by biological processes, such as those from pesticides. 
(EPA Terms of Environment)

chlorine
phosgene 75-44-5 COCl 2 ICSC: 0007
dioxin
hexane

gamma-Hexachlorocyclohexane degradation - Standard metabolic pathway


Epoxide forms during metabolism of pentachlorocyclohexane. This stable halogenated hydrocarbon epoxide may be responsible for the mutagenic and carciogenic effects. (ATSDR, 1997)


  • BENZENE HEXACHLORIDE
  • gamma-BENZENE HEXACHLORIDE
  • BENZENE HEXACHLORIDE-gamma isomer
  • HEX
  • gamma-HEXACHLOR
  • HEXACHLORAN
  • HEXACHLORANE
  • gamma-HEXACHLORBENZENE
  • HEXACHLOROBENZENE
  • 1, 3-HEXACHLOROBUTADIENE
  • HEXACHLOROBUTADIENE
  • 1, 2, 3, 4, 5, 6-HEXACHLOROCYCLOHEXANE
  • HEXACHLOROCYCLOHEXANE
  • HEXANE
  • n-HEXANE
  • gamma-HEXANE LINDANE

In aminals gamma-(HCH) appears tranformed by heptic enzymes to form the following metabolites.

  • 2-CHLOROPHENOL
  • o-CHLOROPHENOL
  • CHLOROBENZENE ICSC: 0642
  • CHLOROCYCLOHEXANE
  • CHLOROCYCLOHEXANAL
  • conjugates of mercapturic acid, gluronide, and sulfate

(Chadwick and Freal 1972a; Chadwick et al. 1978a; Engst et al.1979; Kujawa et al. 1977)

Safety Card -- 1-HYDROXY-2,5-DICHLOROBENZENE 583-78-8 SK8600000
Safety Card -- 1-HYDROXY-3, 5-DICHLOROBENZENE 591-35-5 SK8820000
Safety Card -- 4-HYDROXYCHLOROBENZENE 106-48-9 SK2800000
Safety Card -- 3-HYDROXYCHLOROBENZENE 108-43-0 SK2450000
Safety Card -- 2-HYDROXYCHLOROBENZENE 95-57-8 SK2625000
Safety Card --p-NITROCHLOROBENZENE 100-00-5 CZ1050000
Safety Card -- O-NITROCHLOROBENZENE 88-73-3 CZ0875000
Safety Card -- ORTHO-DICHLOROBENZENE 95-50-1 CZ4500000
Safety Card -- PARA-DICHLOROBENZENE 106-46-7 CZ4550000
Safety Card --PENTACHLOROBENZENE 608-93-5 DA6640000
Safety Card -- 1,2,3,4,5-PENTACHLOROBENZENE 608-93-5 DA6640000
Safety Card -- PERCHLOROBENZENE 118-74-1 DA2975000
Safety Card -- S-TETRACHLOROBENZENE 95-94-3 DB9450000
Safety Card -- SYM-TRICHLOROBENZENE 108-70-3 DC2100100
Safety Card --1,2,4,5-TETRACHLOROBENZENE 95-94-3 DB9450000
Safety Card --1,3,5-TRICHLOROBENZENE 108-70-3 DC2100100

Fisher - Chlorobenzene, Spectrophotometric Grade 108-90-7

Fisher - Chlorobenzene, Reagent ACS (GC) 108-90-7

Safety Card --1,3,5-TRICHLOROBENZENE 108-70-3 DC2100100
Safety Card --1,2,4-TRICHLOROBENZENE 120-82-1 DC2100000
Safety Card -- 1,2,6-TRICHLOROBENZENE 87-61-6 DC2095000
Safety Card --1,2,3-TRICHLOROBENZENE 87-61-6 DC2095000
Safety Card -- UNSYM-TRICHLOROBENZENE 120-82-1 DC2100000
Safety Card -- VIC-TRICHLOROBENZENE 87-61-6 DC2095000

Fisher - Chlorobenzene 108-90-7
Fisher - Chlorobenzene 108-90-7
Fisher - 1,3-Dichlorobenzene 541-73-1
Fisher - 1,4-Dichlorobenzene 106-46-7
Fisher - o-Dichlorobenzene 95-50-1
Fisher - p-Dichlorobenzene 106-46-7
Fisher - 1,2-Dichlorobenzene 95-50-1
Fisher - Hexachlorobenzene 118-74-1

Fisher - 1,2,4-Trichlorobenzene 120-82-1
Fisher - 1,2,4-Trichlorobenzene 120-82-1
Fisher - 1,3,5-Trichlorobenzene 108-70-3
Fisher - 1,2,4-Trichlorobenzene 120-82-1
Fisher - 1,2,3-Trichlorobenzene 87-61-6
Fisher - 2,6-Dichlorobenzenethiol 24966-39-0
Fisher - 4-Chlorobenzenesulfonamide 98-64-6
Fisher - 1,2,4,5-Tetrachlorobenzene 95-94-3
Fisher - 1,2,3,4-Tetrachlorobenzene 634-66-2

ALDRICH CHEMICAL -- 1,2,3,4-TETRACHLOROBENZENE, 98%, 13184-9
ALDRICH CHEMICAL -- 1,3-DICHLOROBENZENE, 98%, 11380-8
ALDRICH CHEMICAL -- 1,4-DICHLOROBENZENE, 99+%, D5682-9
ALDRICH CHEMICAL -- 1-BROMO-2,6-DICHLOROBENZENE, 99%, 16065-2
ALDRICH CHEMICAL -- CHLOROBENZENE, 99+%, SPECTROPHOTOMETRIC GRA
ALDRICH CHEMICAL -- CHLOROBENZENE, 99.9+% 27064-4
ALDRICH CHEMICAL -- HEXACHLOROBENZENE, 99% 17105-0
BAXTER HEALTHCARE BURDICK & JACKSON DIV -- 1,2,4-TRICHLOROBENZENE
BAXTER HEALTHCARE BURDICK & JACKSON DIV -- CHLOROBENZENE
BAXTER HEALTHCARE BURDICK & JACKSON DIV -- O-DICHLOROBENZENE


Mallinckrodt Baker -- mercapturic acid 616-91-1
Mercapturic acid

Metabolites found following immediate exposure via gavage or diet

  • DI-, TRI-, TETRA and PENTACHLOROBENZENES
  • PENTACHLOROHEXANES
  • PENTACHLORO-2-CYCLOHEXEN-1-OL
  • DI-, TRI-, TETRA and PENTACHLOROPHENOLS
  • isomers of TETRACHLORO-2-CYCLOHEXANE-1-OL

(Chadwick and Freal 1972a; Chadwick et al. 1978a; Engst et al.1979; Kujawa et al. 1977)

In vitro studies found gamma-(HCH) converted to 

  • HEXACHLOROBENZENE

(Gopalaswamy and Aiyer 1984)

1-Chlorocyclohexene oxide
beta-Pentachlorocyclohexene
gamma-Pentachlorocyclohexene
Octafluorodichlorocyclohexene

CHEM SERVICE -- 0-669, CHLOROBENZENE
CHEM SERVICE -- 1,2,4,5-TETRACHLOROBENZENE, O-688
CHEM SERVICE -- 1,2,4-TRICHLOROBENZENE, O-689
CHEM SERVICE -- 1,2-DICHLOROBENZENE, O-677
CHEM SERVICE -- 1,3-DICHLOROBENZENE, O-678
CHEM SERVICE -- 1,4-DICHLOROBENZENE, O-679
CHEM SERVICE -- F25 1,2-DICHLOROBENZENE
CHEM SERVICE -- F26 1,3-DICHLOROBENZENE
CHEM SERVICE -- F27 1.4-DICHLOROBENZENE - LABORATORY STANDARD
CHEM SERVICE -- F7 CHLOROBENZENE
CHEM SERVICE -- F8 1,2,4-TRICHLOROBENZENE - LABORATORY STANDARD
SCOTT SPECIALTY GASES -- CHLOROBENZENE

Chemical listings:

chlorinated hydrocarbon epoxide

Heptachlor epoxide (BHC- hexachlorocyclohexane)

di-, tri-, and tetrachlorophenols ICSC: 0573

Metabolization

Derivatives: crude BHC metabolizes to beta, gamma, delta and alpha isomers; gammma BHC metabolizes to gamma-pentachlorocyclohexene

2,3,5,6-TETRACHLOROPHENOL
Phenol, 2,3,5,6-tetrachloro-
2,3,5,6-Tetrachlorohydroxybenzene
C6H2Cl4O
Molecular mass: 231.9
CAS # 935-95-5

hexachlorobenzene hexachlorobenzene is a parent pesticide also may occur as an impurity or metabolite of some other pesticides (e.g., chlorothalonil, DCPA, pentachlorophenol, picloram, quintozene) or as an environmental contaminant.)

05-17-00, http://vm.cfsan.fda.gov/~dms/pes-chem.html

 

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