Chromatographic data and mass spectral diagnostic ions of doxepin and its metabolites produced by C. elegans
| Compound | Molecular Weight | HPLC Retention Time | UV λmax | Mass Spectral Diagnostic Ions | |
|---|---|---|---|---|---|
| Electron ionization | Ammonia PICI | ||||
| min | nm | m/z (relative abundance) | |||
| (E)-3-hydroxy-N-desmethyldoxepin (I) | 281 | 17.3 | 207, 269, 299 | 44(100), 238(22), 281(1.9) | 44(12), 282(100) |
| (E)-4-hydroxy-N-desmethyldoxepin (II) | 281 | 18.2 | 206, 262, 300 | 44(100), 281(4) | 44(15), 282(100) |
| (Z)-8-hydroxy-N-desmethyldoxepin, (E)-2-hydroxy-N-desmethyldoxepin (III) | 281 | 19.2 | 205, 256, 286 | 44(100), 238(10), 281(1.0) | 44(19), 282(100) |
| (E)-8-hydroxy-N-desmethyldoxepin (IV) | 281 | 21.7 | 204, 262, 285 | 44(100), 281(4) | 44(9), 282(100) |
| (E)-3-hydroxydoxepin (V) | 295 | 22.7 | 208, 267, 298 | 58(100), 295(1.2) | 58(26), 296(100) |
| (E)-2-hydroxydoxepin (VI) | 295 | 23.6 | 211, 318 | 58(100), 295(0.8) | 58(25), 296(100) |
| (Z)-8-hydroxydoxepin (VII) | 295 | 24.1 | 205, 261, 284 | 58(100), 295(0.8) | 58(24), 296(100) |
| (E,Z)-N-desmethyldoxepin (IX) | 265 | 26.6 | 214, 254, 297 | 44(100), 265(1.2) | 44(10), 266(100) |
| (E,Z)-doxepin-N-oxide (X) | 295 | 30.2 | 204, 260, 298 | 58(100), 295(0.8) | 58(14), 296(100) |
| (E,Z)-doxepin (XI) | 279 | 34.1 | 207, 256, 297 | 58(100), 279(0.4) | 58(15), 280(100) |
| (E)-N-formyl-N-desmethyldoxepin (XII) | 293 | 34.8 | 206, 256, 298 | 221(29), 234(100), 293(16) | 234(19), 294(100), 311(15) |
| (E)-N-acetyldidesmethyldoxepin (XIII) | 293 | 35.6 | 207, 255, 297 | 219(50), 221(32), 234(100), 293(21) | 234(15), 294(100), 311(22) |
| (E)-N-acetyl-N-desmethyldoxepin (XIV) | 307 | 37.9 | 207, 256, 297 | 44(67), 219(37), 221(26), 234(100), 307(14) | 234(12), 308(100), 325(5) |