Table 3.
5F-CUMYL-PICA metabolites following incubation with rat and human hepatocytes, and in rat plasma and urine following a 3 mg/kg i.p. injection
| Metabolite | RT (min) | Transformation | Molecular ion [M+H]+ (m/z) | Major product ions (m/z) | Rat hepatocyte | Human hepatocyte | Rat plasma | Rat urine |
|---|---|---|---|---|---|---|---|---|
| F1 | 4.15 | Fluoropentyl dealkylation + hydroxylation (α,α-dimethylbenzyl) + glucuronidation | 471.17 | 177, 161, 135 | ✓ | ✓ | ||
| F2 | 4.44 | Oxidative defluorination + hydroxylation + glucuronidation | 557.24 | 381, 263 | ✓ | |||
| F3 | 4.51 | Fluoropentyl dealkylation + hydroxylation (indole) + glucuronidation | 471.17 | 177, 119 | ✓ | ✓ | ✓ | ✓ |
| F4 | 4.65 | Oxidative defluorination + hydroxylation + glucuronidation | 557.24 | 381, 263 | ✓ | ✓ | ✓ | |
| F5 | 4.80 | Oxidative defluorination + hydroxylation + glucuronidation | 557.24 | 381, 263 | ✓ | ✓ | ||
| F6 | 4.87 | Fluoropentyl dealkylation + hydroxylation (indole) + glucuronidation | 471.17 | 177, 119 | ✓ | ✓ | ✓ | |
| F7 | 5.11 | Fluoropentyl dealkylation + hydroxylation (α,α-dimethylbenzyl) | 295.14 | 161, 144, 135, 118 | ✓ | ✓ | ✓ | |
| F8 | 5.17 | Fluoropentyl dealkylation + hydroxylation (α,α-dimethylbenzyl) | 295.14 | 161, 144, 135, 118 | ✓ | ✓ | ✓ | |
| F9 | 5.30 | Fluoropentyl dealkylation + hydroxylation (indole) | 295.14 | 177, 160, 134, 119 | ✓ | ✓ | ✓ | |
| F10 | 5.34 | Fluoropentyl dealkylation + hydroxylation (indole) | 295.14 | 177, 160, 134, 119 | ✓ | ✓ | ✓ | |
| F11 | 5.58 | Oxidative defluorination + carboxylation + hydroxylation (α,α-dimethylbenzyl) | 395.19 | 261, 244, 218, 200, 144, 135 | ✓ | ✓ | ||
| F12 | 5.61 | Hydroxylation + glucuronidation | 559.24 | 382, 248 | ✓ | |||
| F13 | 5.64 | Oxidative defluorination + carboxylation + hydroxylation (indole) | 395.19 | 277, 260, 234, 216, 119 | ✓ | ✓ | ✓ | |
| F14 | 5.66 | Dihydroxylation (α,α-dimethylbenzyl, indole/fluoropentyl) | 399.21 | 265, 248, 135 | ✓ | ✓ | ||
| F15 | 5.68 | Oxidative defluorination + oxidation | 381.22 | 263, 246, 202, 119 | ✓ | ✓ | ||
| F16 | 5.70 | Hydroxylation + glucuronidation | 559.24 | 382, 248 | ✓ | ✓ | ✓ | |
| F17 | 5.72 | Dihydroxylation (indole/fluoropentyl) | 399.21 | 281, 264, 238, 119 | ✓ | ✓ | ✓ | |
| F18 | 5.78 | Hydroxylation + glucuronidation | 559.24 | 382, 248 | ✓ | ✓ | ✓ | ✓ |
| F19 | 6.01 | Oxidative defluorination + glucuronidation | 541.25 | 247, 230, 204, 186, 119 | ✓ | |||
| F20 | 6.42 | Fluoropentyl dealkylation | 279.15 | 161, 144, 119 | ✓ | ✓ | ✓ | |
| F21 | 6.68 | Oxidative defluorination + carboxylation | 379.21 | 261, 244, 218, 200, 119 | ✓ | ✓ | ✓ | |
| F22 | 6.74 | Oxidative defluorination | 365.22 | 247, 230, 204, 119 | ✓ | ✓ | ✓ | |
| F23 | 6.79 | Hydroxylation (indole, fluoropentyl) | 383.21 | 265, 248, 222, 119 | ✓ | ✓ | ✓ | |
| F24 | 6.85 | Hydroxylation (indole, fluoropentyl) | 383.21 | 265, 248, 222, 119 | ✓ | ✓ | ✓ | |
| F25 | 6.92 | Hydroxylation (indole, fluoropentyl) | 383.21 | 265, 248, 222, 119 | ✓ | ✓ | ||
| F26 | 7.03 | Hydroxylation (benzene) | 383.21 | 249, 232, 206, 135, 107 | ✓ | ✓ | ✓ | |
| F27 | 7.31 | Hydroxylation (indole, fluoropentyl) | 383.21 | 265, 248, 222, 119 | ✓ | ✓ | ||
| F28 | 7.55 | Hydroxylation (benzene) | 383.21 | 249, 232, 206, 135, 107 | ✓ | |||
| 5F-CUMYL-PICA | 8.11 | Parent compound | 367.21 | 249, 232, 206, 119, 91 | ✓ | ✓ | ✓ |
Ticks denote detection of compounds in a given matrix