Supplementary Table2Data mining with MetabolitePilot for the two authentic urine specimens associated with AB-PINACA intake. The table summarizes metabolites that were among the 20 most intense metabolites for each sample with andwithout hydrolysis. Only metabolites >250 Da and within ±5 ppm mass shift were included and the corresponding ID of the hepatocyte experiments assigned. Metabolites sorted by retention time, ranks are given for each specimen.

Name / Formula / m/z / Retention time
min / Corresponds to ... / Urine#1 hydrolysis / Urine#1, nohydrolysis / Urine#2hydrolysis / Urine#2 nohydrolysis
Internal amide hydrolysis + Di-Oxidation / C13H16N2O4 / 265.1189 / 3.31 / a / 2 / 1 / 1 / 1
Internal amide hydrolysis + Carboxylation / C13H14N2O4 / 263.1026 / 3.53 / b / 19
Internal amide hydrolysis + Epoxide hydrolysis / C13H18N2O4 / 267.1345 / 6.48 / c / 9 / 4 / 5 / 4
Epoxide hydrolysis + Oxidation / C18H28N4O5 / 381.2143 / 6.74 / d / 16 / 10
Di-Oxidation / C18H26N4O4 / 363.2033 / 8.40 / e / 18 / 18
Di-Oxidation / C18H26N4O4 / 363.2038 / 8.99 / A1 / 19 / 13
Ketone Formation + Oxidation / C18H24N4O4 / 361.1882 / 9.35 / A2 / 11 / 9 / 12 / 12
Epoxide hydrolysis to dihydrodiol / C18H28N4O4 / 365.2197 / 9.78 / A3 / 6 / 5 / 7 / 14
Amide hydrolysis + Oxidation / C18H25N3O4 / 348.1922 / 9.81 / f / 14
Amide hydrolysis + Di-Oxidation / C18H25N3O5 / 364.1879 / 10.21 / g / 5 / 6 / 6
Amide hydrolysis + Di-Oxidation / C18H25N3O5 / 364.1873 / 10.42 / h / 16 / 17
Amide hydrolysis + Oxidation + Ketone Formation / C18H23N3O5 / 362.1727 / 10.48 / i / 17 / 12 / 20 / 17
Dealkylation + Carboxylation / C13H15N3O3 / 262.1189 / 10.49 / j / 20
Amide hydrolysis + Di-Oxidation / C18H25N3O5 / 364.1878 / 10.65 / k / 10 / 6 / 9 / 10
Amide hydrolysis + Carboxylation (+ Glucuronidation) / C18H23N3O5 / 362.1727 / 11.15 / l / 15
Oxidation / C18H26N4O3 / 347.2090 / 11.27 / A6 / 17 / 19 / 19
Carboxylation / C18H24N4O4 / 361.1888 / 11.32 / A7 / 8 / 3 / 8 / 8
Amide hydrolysis + Ketone Formation / C18H23N3O4 / 346.1774 / 11.60 / m / 8 / 11
Amide hydrolysis + Epoxide hydrolysis / C18H27N3O5 / 366.2036 / 11.83 / n / 13 / 16 / 15
Amide hydrolysis + Carboxylation / C18H23N3O5 / 362.1728 / 13.28 / A12 / 7 / 2 / 10 / 9
Amide hydrolysis + Oxidation / C18H25N3O4 / 348.1928 / 13.35 / A13 / 4 / 4 / 5
Amide hydrolysis + Ketone Formation / C18H23N3O4 / 346.1775 / 14.29 / A16 / 1 / 2 / 2
Amide hydrolysis + Oxidation / C18H25N3O4 / 348.1924 / 14.43 / o / 18 / 11 / 11 / 13
Oxidation / C18H26N4O3 / 347.2081 / 15.07 / A17 / 20
Internal amide hydrolysis + Hydrogenation / C13H18N2O / 219.1495 / 15.63 / p / 15
Oxidation / C18H26N4O3 / 347.2088 / 16.28 / q / 18
Amide hydrolysis + Oxidation / C18H25N3O4 / 348.1927 / 17.32 / r / 12 / 14 / 14
Amide hydrolysis + Glucuronidation / C24H33N3O9 / 508.2297 / 17.48 / s / 15 / 16
Amide hydrolysis + Glucuronidation / C24H33N3O9 / 508.2309 / 17.64 / A21 / 7 / 13 / 7
Amide hydrolysis / C18H25N3O3 / 332.1983 / 21.76 / A23 / 3 / 3 / 3

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