Table 1.
25CN-NBOMe phase I and II metabolites, their protonated precursor ion exact masses and retention times (RT) detected in rat urine (RU), human liver microsomes (HLM), and C. elegans (CE). Data were measured with the UltiMate 3000 (Thermo) coupled to the TripleTOF 5600 (AB Sciex) LC-MS system.
| No. | Metabolite | Precursor ion Exact Mass [m/z] |
RT [min] | RU | HLM | CE |
|---|---|---|---|---|---|---|
| M1 | 25CN-NBOMe | 327.1709 | 7.9 | I | I | I |
| M2 | hydroxy-25CN-NBOMe isomer 1 | 343.1658 | 7.4 | I | ||
| M3 | hydroxy-25CN-NBOMe isomer 2 | 343.1658 | 7.3 | I | I | I |
| M4 | hydroxy-25CN-NBOMe isomer 3 | 343.1658 | 7.7 | D | ||
| M5 | dehydro-25CN-NBOMe | 325.1552 | 7.3 | D | I | |
| M6 | dehydro-25CN-NBOMe-N-oxide | 341.1501 | 9.8 | I | D | |
| M7 | dehydro-hydroxy-25CN-NBOMe | 341.1501 | 10.1 | D | I | |
| M8 | O-demethyl-hydroxy-25CN-NBOMe | 329.1501 | 6.9 | D | I | |
| M9 | O-demethyl-25CN-NBOMe | 313.1552 | 7.5 | I | I | I |
| M10 | 25CN-NBOH | 313.1552 | 7.6 | I | I | I |
| M11 | O,O-bis-demethyl-25CN-NBOMe | 299.1396 | 6.8 | I | ||
| M12 | O-demethyl-25CN-NBOH | 299.1396 | 7.1 | I | I | D |
| M13 | O,O-bis-demethyl-hydroxy-25CN-NBOMe isomer 1 | 315.1345 | 5.8 | D | ||
| M14 | O,O-bis-demethyl-hydroxy-25CN-NBOMe isomers 2, 3, 4 | 315.1345 | 6.1–6.8 | D | ||
| M15 | O-demethyl-dehydro-hydroxy-25CN-NBOMe | 327.1345 | 9.2 | D | ||
| M16 | O,O-bis-demethyl-dehydro-25CN-NBOMe | 297.1239 | 6.9 | D | ||
| M17 | O,O-bis-demethyl-25CN-NBOH | 285.1239 | 5.7 | D | ||
| M18 | 2C-CN | 207.1134 | 5.7 | I | I | I |
| M19 | O-demethyl-2C-CN | 193.0977 | 4.9 | I | D | |
| M20 | O-demethyl-deamino-hydroxy-2C-CN | 194.0817 | 6.0 | D | ||
| M21 | O-demethyl-deamino-carboxy-2C-CN | 208.0610 | 5.7 | I | ||
| M22 | 2C-CONH2-NBOMe | 345.1814 | 7.1 | D | ||
| M23 | O-demethyl-2C-CONH2 | 211.1078 | 4.0. | D | ||
| M24 | O,O-bis-demethyl-hydroxy-2C-COOH-NBOMe | 334.1291 | 5.4 | D | ||
| M25 | 2C-COOH | 226.1079 | 4.5 | D | ||
| M8I G | O-demethyl-hydroxy-25CN-NBOMe glucuronide isomer 1 | 505.1822 | 6.2 | I | ||
| M8 G | O-demethyl-hydroxy-25CN-NBOMe glucuronide isomer 2 | 505.1822 | 6.7 | D | ||
| M9 G | O-demethyl-25CN-NBOMe glucuronide | 489.1873 | 6.9 | I | D | |
| M11 G | O,O-bis-demethyl-25CN-NBOMe glucuronide | 475.1717 | 6.1 | I | D | |
| M13 G | O,O-bis-demethyl-hydroxy-25CN-NBOMe glucuronide isomer 1 | 491.1666 | 5.4 | D | ||
| M14 G | O,O-bis-demethyl-hydroxy-25CN-NBOMe glucuronide isomer 2 | 491.1666 | 6.2 | D | ||
| M16 G | O,O-bis-demethyl-dehydro-25CN-NBOMe glucuronide | 473.1560 | 5.6 | D | ||
| M17 G | O,O-bis-demethyl-25CN-NBOH glucuronide | 461.1560 | 5.4 | I | ||
| M19 G | O-demethyl-2C-CN glucuronide | 369.1298 | 4.0 | D | ||
| M26 G | oxo-2C-CN glucuronide | 397.1247 | 4.5 | D | ||
| M3 S | hydroxy-25CN-NBOMe sulfate | 423.1226 | 7.4 | D | ||
| M8 S | O-demethyl-hydroxy-25CN-NBOMe sulfate | 409.1069 | 6.9 | I | ||
| M9 S | O-demethyl-25CN-NBOMe sulfate | 393.112 | 7.7 | D | ||
| M11 S | O,O-bis-demethyl-25CN-NBOMe sulfate | 379.0964 | 6.9 | I | ||
| M12 S | O-demethyl-25CN-NBOH sulfate | 379.0964 | 7.1 | D | ||
| M13 S | O,O-bis-demethyl-hydroxy-25CN-NBOMe sulfate isomer 1 | 395.0913 | 5.8 | D | ||
| M14 S1 | O,O-bis-demethyl-hydroxy-25CN-NBOMe sulfate isomer 2 | 395.0913 | 6.3 | D | ||
| M14 S2 | O,O-bis-demethyl-hydroxy-25CN-NBOMe sulfate isomer 3 | 395.0913 | 6.8 | D | ||
| M17 S1 | O,O-bis-demethyl-25CN-NBOH sulfate isomer 1 | 365.0807 | 5.7 | D | ||
| M17 S2 | O,O-bis-demethyl-25CN-NBOH sulfate isomer 2 | 365.0807 | 6.4 | D | ||
| M26 S | oxo-2C-CN sulfate | 301.0494 | 5.0 | I | ||
| M19 Ac | O-demethyl-2C-CN N-acetyl isomer 1 | 235.1083 | 7.1 | I | ||
| M19 Ac | O-demethyl-2C-CN N-acetyl isomer 2 | 235.1083 | 7.3 | I | ||
| M19 Ac G | O-demethyl-2C-CN N-acetyl glucuronide | 411.1404 | 5.9 | I | ||
| M19 Ac S | O-demethyl-2C-CN N-acetyl sulfate | 315.0651 | 6.2 | D | ||
| M27 Ac | hydroxy-2C-CN N-acetyl | 265.1188 | 5.6 | D |
I = identified by matching precursor ion mass and recorded HR-MS/MS spectrum; D = detected based on the precursor ion exact mass only.