Proton NMR data of irbesartan and its metabolites determined in DMSO-d6
| 1H | Irbesartan | M1 | M2 | M3 | M4 | M5 | M6 | M7 | M8 | M9 |
|---|---|---|---|---|---|---|---|---|---|---|
| 8′ | 7.63 (1H,d) | 7.63 (1H,d) | 7.64 (1H,d) | 7.62 (1H,d) | 7.63 (1H,d) | 7.61 (1H,d) | 7.6 (1H,d) | 7.62 (1H,d) | 7.8 (1H,d) | 7.56 (1H,bd) |
| 7′ | 7.62 (1H,t) | 7.6 (1H,t) | 7.63 (1H,t) | 7.56 (1H,t) | 7.6 (1H,t) | 7.58 (1H,t) | 7.54 (1H,t) | 7.58 (1H,t) | 7.62 (1H,t) | 7.44 (1H,bm) |
| 6′ | 7.52 (1H,t) | 7.52 (1H,t) | 7.53 (1H,t) | 7.48 (1H,t) | 7.52 (1H,t) | 7.50 (1H,t) | 7.47 (1H,t) | 7.5 (1H,t) | 7.54 (1H,t) | 7.38 (1H,bm) |
| 5′ | 7.49 (1H,d) | 7.48 (1H,d) | 7.51 (1H,d) | 7.46 (1H,d) | 7.49 (1H,d) | 7.45 (1H,d) | 7.43 (1H,d) | 7.46 (1H,d) | 7.47 (1H,d) | 7.34 (1H,d) |
| 1′ 2′ 3′ 4′ | 7.08 (2H,d) | 7.08 (2H,d) | 7.07 (4H,d) | 7.04 (4H,q) | 7.07 (4H,q) | 7.08 (2H,d) | 7.08 (2H,d) | 7.08 (2H,d) | 7.13 (2H,d) | 7.08 (2H,d) |
| 7.05 (2H,d) | 7.04 (2H,d) | 7.03 (2H,d) | 7.05 (2H,d) | 7.03 (2H,d) | 7.07 (2H,d) | 6.98 (2H,d) | ||||
| benz | 4.66 (2H,s) | 4.66 (2H,s) | 4.68 (2H,s) | 4.64 (2H,s) | 4.66 (2H,s) | 4.65 (2H,s) | 4.67 (2H,s) | 4.63 (2H,s) | 4.67 (2H,s) | 4.63 (2H,s) |
| 1b | 2.28 (2H,t) | 2.35 (2H,m) | 2.53-a | 2.32 (2H,t) | 2.36 (2H,m) | 2.27 (2H,t) | 2.5 (2H,t) | 2.28 (2H,t) | 2.31 (2H,t) | 2.3 (2H,t) |
| 2b | 1.47 (2H,quin) | 1.55 (2H,m) | 2.73 (2H,t) | 1.74 (2H,quin) | 1.58 (2H,m) | 1.45 (2H,quin) | 2.74 (2H,t) | 1.48 (2H,quin) | 1.48 (2H,quin) | 1.48 (2H,quin) |
| 3b | 1.23 (2H,m) | 3.58 (1H,m) | — | 2.23 (2H,t) | 3.59 (1H,m) | 1.24 (2H,m) | — | 1.26 (2H,m) | 1.26 (2H,m) | 1.26 (2H,m) |
| 4b-Me | 0.8 (3H,t) | 1.0 (3H,d) | 2.07 (3H,s) | — | 1.0 (3H,d) | 0.78 (3H,t) | 2.07 (3H,s) | 0.8 (3H,t) | 0.8 (3H,t) | 0.8 (3H,t) |
| 1 2 3 4 | 1.82 (6H,b) | 2.04 (2H,m) | 2.01 (2H,m) | 1.84 (6H,b) | 1.82 (6H,b) | 2.04 (2H,m) | 1.8 (6H,b) | 2.02 (2H,m) | 1.82 (6H,b) | 1.82 (6H,b) |
| 1.65 (2H,b) | 1.87 (1H,m) | 1.62–1.86 (3H,m) | 1.66 (2H,b) | 1.65 (2H,b) | 1.87 (1H,dd) | 1.6 (2H,b) | 1.84 (1H,m) | 1.66 (2H,b) | 1.64 (2H,b) | |
| 1.72 (2H,m) | 1.76 (1H,dd) | 1.74 (2H,m) | ||||||||
| 1.56 (1H,m) | 1.47 (1H,m) | 1.69 (1H,m) | 1.66 (1H,dd) | |||||||
| 1.52 (1H,m) | ||||||||||
| 2 or 3 | — | 4.37 (1H,m) | 4.34 (1H,m) | — | — | 4.37 (1H,m) | — | 4.32 (1H,m) | — | — |
| 2 or 3 ring | — | 4.74 (1H,d) | 4.74 (1H,d) | — | — | 4.76 (1H,d) | — | 4.7 (1H,d) | — | — |
| 1" | — | — | — | — | — | — | — | — | 5.77 (1H,d)3-c | — |
| 2" | — | — | — | — | — | — | — | — | 3.85 (1H,m)3-c | — |
| 3" | — | — | — | — | — | — | — | — | ∼3.3b,c | — |
| 4" | — | — | — | — | — | — | — | — | ∼3.3b,c | — |
| 5" | — | — | — | — | — | — | — | — | 3.7 (1H,b)3-c | — |
| 2" OH | — | — | — | — | — | — | — | — | 5.41 (1H,d)3-c | — |
| 3" OH | — | — | — | — | — | — | — | — | 5.2 (1H,d)3-c | — |
Values are chemical shifts (in ppm). b, broad; s, singlet; d, doublet; t, triplet; q, quartet; quin, quintuplet; m, multiplet.