LC-MS/MS characteristics and 1H NMR spectra of the aromatic hydrogen atoms of the GSH conjugates of clozapine
| Conjugate | 1H NMR Spectra | LC-MS/MS-Mass Spectra | ||
|---|---|---|---|---|
| Assignmenta | δ ppm (Intensity) | Multiplicity: Coupling Constants | m/z (Intensity)b | |
| CG-1 | H1/H4 | 7.30 (1H) | d of d: 2JHH, 7 Hz; 3JHH, 1.5 Hz | 623.23 (MH+; 100%) |
| H2/H3 | 7.08 (1H) | d of t: 2JHH 7.5 Hz, 3JHH 1.5 Hz | 614.22 (8%); 575.17 (6%) | |
| H3/H2 | 7.41 (1H) | d of t: 2JHH 7.5 Hz, 3JHH 1.5 Hz | 503.18 (37%); 446.12 (1%) | |
| H4/H1 | 7.10 (1H) | d: 2JHH 7.5 Hz | 359.12 (29%); 302.06 (12%) | |
| H7/H9 | 7.23 (1H) | d: 2JHH 2.5 Hz | ||
| H9/H7 | 6.96 (1H) | d: 2JHH 2.5 Hz | ||
| CG-3 | H1/H4 | 7.36 (1H) | d: 2JHH 8 Hz | 623.23 (MH+; 100%) |
| H2/H3 | 7.07 (1H) | d of t: 2JHH 7 Hz, 3JHH 1.5 Hz | 614.22 (1%); 503.18 (23%) | |
| H3/H2 | 7.37 (1H) | t: 2JHH 7 Hz | 446.12 (1%); 359.12 (41%) | |
| H4/H1 | 6.99 (1H) | d: 2JHH 8 Hz | 302.06 (6%) | |
| H6 | 7.02 (1H) | d: 2JHH 8 Hz | ||
| H7 | 6.83 (1H) | d: 2JHH 8 Hz | ||
| CG-4 | H1/H4 | 7.28 (1H) | d of d: 2JHH 8 Hz, 3JHH 1.5 Hz | 623.23 (MH+; 100%) |
| H2/H3 | 7.04 (1H) | t: 2JHH 7 Hz | 614.22 (8%); 575.17 (3%) | |
| H3/H2 | 7.37 (1H) | d of t: 2JHH 7 Hz, 3JHH 1.5 Hz | 503.18 (44%); 446.12 (4%) | |
| H4/H1 | 7.07 (1H) | d: 2JHH 8 Hz | 359.12 (17%); 302.06 (4%) | |
| H6/H9 | 7.01 (1H) | s | 243.06 (5%) | |
| H9/H6 | 7.03 (1H) | s | ||
| CG-5 | H1/H4 | 6.95 (1H) | d: 3JHH 1 Hz | 623.23 (MH+; 100%) |
| H3 or H2 | 6.85 (1H) | d of d: 2JHH 8.5 Hz, 3JHH 2 Hz | 614.22 (6%); 575.17 (10%) | |
| H4/H1 | 6.78 (1H) | d: 2JHH 9 Hz | 503.18 (27%); 446.12 (25%) | |
| H6 | 6.96 (1H) | d: 2JHH 9 Hz | 359.12 (15%); 302.06 (13%) | |
| H7 | 7.45 (1H) | d of d: 2JHH 9 Hz, 3JHH 2 Hz | 243.06 (34%) | |
| H9 | 7.37 (1H) | d: 2JHH 2 Hz | ||
| CG-6 | H1/H4 | 7.00 (1H) | d of d: 2JHH 8 Hz, 3JHH 2 Hz | 598.25 (MH+; 100%) |
| H2/H3 | 7.35 (1H) | d of t: 2JHH 7.5 Hz, 3JHH 1.5 Hz | 580.24 (8%); 469.20 (77%) | |
| H3/H2 | 7.04 (1H) | d of t: 2JHH 7.5 Hz, 2JHH 1 Hz | 412.20 (4%); 325.15 (24%) | |
| H4/H1 | 7.30 (1H) | d of d: 2JHH 7.5 Hz, 3JHH 1 Hz | 268.09 (6%) | |
| H6 | 6.82 (1H) | d: 2JHH 8 Hz | ||
| H7 | 7.01 (1H) | d: 2JHH 8 Hz | ||
| H9 | 7.12 (1H) | d: 3JHH 2 Hz | ||
↵a Absolute assignment of protons was not possible; therefore, each signal is indicated by two assignments corresponding to two possible solutions: 1) assignments before the slash correspond to solution 1 and 2) assignments after the slash correspond to solution 2.
↵b Electrospray spectra (LC-MS/MS) were acquired using nitrogen as collision gas with a collision energy of 25 V.