Structure of the glutathione adduct of activated 3-methylindole indicates that an imine methide is the electrophilic intermediate.

@article{Nocerini1985StructureOT,
  title={Structure of the glutathione adduct of activated 3-methylindole indicates that an imine methide is the electrophilic intermediate.},
  author={Mark R Nocerini and Garold S. Yost and James Reynolds Carlson and D J Liberato and Roger G Breeze},
  journal={Drug metabolism and disposition: the biological fate of chemicals},
  year={1985},
  volume={13 6},
  pages={690-4}
}
Goat lung microsomes were incubated with glutathione (GSH) and 3-methylindole (3MI) to produce an adduct between GSH and an electrophilic metabolite of 3MI. The GSH-3MI adduct was purified by reverse-phase HPLC, and its structure elucidated by UV and NMR spectrometry and by thermospray LC/MS. The adduct was shown to be 3-[(glutathion-S-yl)-methyl]indole. Since nucleophilic GSH adds to the methyl position of 3MI without the incorporation of oxygen into the molecule, an epoxide metabolite is… CONTINUE READING

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