TABLE 6.

Metabolite profiling of butonitazene, isotonitazene and protonitazens in human liver microsomes and liver S9 fractions, indicating the presence (√) of putative metabolites.

€Compound	m/z	HLM	HL S9
Butonitazene
Parent	425.255	√	√
Hydroxylation	441.2499	√	√
N-Desethylation	397.2238	√	√
Dealkylation	369.1921	√	√
Desethylation + Dealkylation	341.1908	√	√
Desethylation + Hydroxylation	413.2138	√	√
Isotonitazene
Parent	411.239	√	√
Hydroxylation	427.239	√	√
N-Desethylation	383.208	√	√
Dealkylation	369.171	√	-
N-Desethylation + Dealkylation	341.150	√	√
N-Desethylation + Hydroxylation	399.197	√	√
Depropylated-demethylated	355.176	√	√
N-De-ethylamination and Dealkylation	312.130	√	√
N-desethylation, debutylation	313.130	√	√
Protonitazene
Parent	411.239	√	√
Hydroxylation	427.234	√	√
N-Desethylation	383.208	√	√
Dealkylation	369.180	√	√
N-Desethylated + Dealkylated	341.150	√	√
Demethylated + Dealkylation	355.176	√	√
De-aminopentylated	340.160	√	√
N-Desethylation + Hydroxylation	399.197	√	√