Table 2.
MDMB-4CN-BUTINACA metabolites with biotransformation; molecular formulas; mean retention times; exact (calculated) masses of the protonated molecules; mass errors from all samples; peak areas after 1-, 3-, and 5-h incubations for two replicate samples; the percentage of the total peak area of metabolites across all incubations; and major fragment ions (also indicative of biotransformation)
| Met # | Biotransformation | Formula | Mean RT (min) | Exact mass [M + H]+ (m/z) | Average mass error (ppm) | #1 peak area ( × 103) | #2 peak area ( × 103) | % | Major fragment ions | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 h | 3 h | 5 h | 1 h | 3 h | 5 h | ||||||||
| MDMB-4CN-BUTINACA | C20H26N4O3 | 9.33 | 371.2078 | 28.46 | 14,300 | 251 | 936 | 15,200 | 284 | 934 | – | 145.0396, 226.0975 | |
| M1 | Ester hydrolysis | C19H24N4O3 | 7.42 | 357.1921 | 10.40 | 10,200 | 11,400 | 12,400 | 10,300 | 11,800 | 12,800 | 78.6 | 145.0396, 226.0975 |
| M2 | Ester hydrolysis + dehyd | C19H22N4O3 | 7.21 | 355.1765 | 2.30 | 3440 | 429 | 799 | 3590 | 489 | 987 | 11.1 | 145.0396, 226.0975 |
| M3 | Ester hydrolysis + monoOH (tert-butyl) | C19H24N4O4 | 5.49 | 373.1870 | 1.03 | 383 | 775 | 733 | 380 | 804 | 829 | 4.5 | 145.0396, 226.0975 |
| M4 | Ester hydrolysis + dehyd + monoOH (tert-butyl) | C19H22N4O4 | 6.26 | 371.1714 | −0.77 | 296 | 306 | 304 | 302 | 316 | 345 | 2.1 | 145.0396, 226.0975 |
| M5 | Decyanation to carboxylic acid | C19H25N3O5 | 7.78 | 376.1867 | −0.17 | 356 | 186 | 100 | 363 | 212 | 157 | 1.6 | 87.0441, 145.0396, 231.0764 |
| M6 | Ester hydrolysis + decyanation to carboxylic acid | C18H23N3O5 | 6.12 | 362.1710 | −1.62 | 60 | 133 | 102 | 59 | 142 | 119 | 0.7 | 87.0441, 145.0396, 231.0764 |
| M7 | Ester hydrolysis + GLUC | C25H32N4O9 | 5.86 | 533.2242 | −2.13 | 45 | 94 | 126 | 42 | 96 | 130 | 0.6 | 145.0397, 226.0971 |
| M8 | Carboxylation (tert-butyl) | C20H24N4O5 | 6.67 | 401.1819 | −1.36 | 38 | 45 | 47 | 36 | 44 | 44 | 0.3 | 55.0542, 145.0396, 226.0975 |
| M9 | Ester hydrolysis + decyanation to alcohol | C18H25N3O4 | 6.21 | 348.1918 | −3.24 | 21 | 38 | 29 | 21 | 42 | 35 | 0.2 | 73.0648, 86.0964, 145.0396, 217.0972 |
| M10 | MonoOH (tert-butyl) + GLUC | C26H34N4O10 | 5.23 | 563.2348 | −1.59 | 27 | 32 | 29 | 30 | 33 | 25 | 0.2 | 145.0396, 226.0975 |
| M11 | Dihydrodiol (indazole) | C20H28N4O5 | 5.73 | 405.2132 | −2.92 | 31 | n.d | n.d | 31 | n.d | 23 | 0.1 | 161.0346, 242.0924, 260.1030 |
| M12 | N-dealkylation + ester hydrolysis | C14H17N3O3 | 5.71 | 276.1343 | −2.94 | n.d | n.d | 22 | n.d | 22 | n.d | 0.1 | 86.0964, 145.0396 |
Metabolites are ordered from most to least abundant by average peak area across all incubations
n.d. not detected