Toxicological Review for 2-Methylnaphthalene (CAS No. 91-57-6 ...
Toxicological Review for 2-Methylnaphthalene (CAS No. 91-57-6 ...
Toxicological Review for 2-Methylnaphthalene (CAS No. 91-57-6 ...
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H O<br />
[ ] putative metabolite<br />
CYP cytochrome P450 enzyme(s)<br />
EH epoxide hydrolase<br />
* Metabolites identified in vitro only<br />
OH<br />
5,6-dihydrodiol<br />
H O<br />
SG<br />
CH<br />
3<br />
CH 3<br />
GS<br />
OH<br />
CH 3<br />
Hydroxy glutathionyl dihydro-2-methylnaphthalenes*<br />
H O<br />
H O<br />
OH<br />
EH<br />
O<br />
7,8-dihydrodiol<br />
7-methyl -2-naphthol<br />
5,6-epoxide<br />
CH 3<br />
CH 3<br />
EH<br />
OH<br />
CH 3<br />
2-Naphthaldehyde*<br />
Figure 2: Metabolism of 2-methylnaphthalene (adapted from Buckpitt and Franklin, 1989; Shultz et al.,<br />
2001; Teshima et al., 1983).<br />
9<br />
O<br />
OH<br />
2-Hydroxymethylnaphthalene<br />
CH 3<br />
7-methyl -1-naphthol<br />
O<br />
CH 3<br />
2-<strong>Methylnaphthalene</strong><br />
7,8-epoxide<br />
H O<br />
CYP<br />
CYP<br />
CYP CYP<br />
CYP<br />
SG<br />
CH 3<br />
O<br />
2-Naphthoic acid<br />
3,4-epoxide<br />
OH<br />
O<br />
CH 3<br />
SG<br />
OH<br />
O<br />
NH<br />
2-Naphthuric acid<br />
CH 3<br />
O<br />
OH<br />
OH<br />
3,4-dihydrodiol<br />
SG<br />
S<br />
H O<br />
CH 3<br />
OH<br />
Hydroxy glutathionyl dihydro-2-methylnaphthalenes*<br />
CH 3 GS<br />
SG<br />
OH<br />
CH<br />
3<br />
1-glutathionyl -7-methylnaphthalene<br />
Hydroxy glutathionyl dihydro-2-methylnaphthalenes*<br />
O<br />
NH 2<br />
CH<br />
3<br />
OH<br />
CH 3<br />
7-methyl -1-naphthylcysteine<br />
CH 3<br />
EH<br />
glucuronidation