TABLE 3.
1H and 13C DEPTQ NMR data for 1CP-LSD hemitartrate (2:1) in DMSO-d6 at 600/150 MHz
| ||
|---|---|---|
| No. | 13C [δ/ppm] | 1H [δ/ppm] |
| 1 | – | – |
| 2 | 120.09 | 7.89 (d, J = 1.6 Hz, 1H) |
| 3 | 116.25 | – |
| 4 | 26.02 | 2.51–2.48 (m, 4α-H) *coalescing with DMSO 3.52 (dd, J = 15.3, 5.5 Hz, 4β-H, 1 H) |
| 5 | 61.75 | 3.15–3.13 (m, H-5β, 1H) |
| 6 | – | – |
| 7 | 55.24 | 3.04 (dd, J = 11.1, 5.0 Hz, H-7α, 1H) 2.66 (t, J = 9.8 Hz, H-7β, 1H) *partially coalescing with H-24 |
| 8 | 38.83 | 3.85–3.82 (m, H-8α, 1H) |
| 9 | 121.85 | 6.36 (s, 1H) |
| 10 | 133.34 | – |
| 11 | 127.73 | – |
| 12 | 116.66 | 7.36 (d, J = 7.5 Hz, 1H) |
| 13 | 125.92 | 7.30 (t, J = 7.8 Hz, 1H) |
| 14 | 114.92 | 8.01 (d, J = 8.0 Hz, 1H) |
| 15 | 133.22 | – |
| 16 | 127.61 | – |
| 17 | 43.04 | 2.53 (s, 3H) |
| 18 | 170.30 | – |
| 19 | – | – |
| 20 | 41.59 | 3.45 (q, J = 7.1 Hz, 2H) |
| 20 | 39.56 | 3.32 (AB qq, J20,20 = 13.8, J20,21 = 7.0 Hz, 2 H) |
| 21 | 14.82 | 1.19 (t, J = 7.1 Hz, 3H) |
| 21 | 13.06 | 1.12–1.03 (m, 3H) *coalescing with H-25 |
| 22 | 172.20 | – |
| 23 | – | – |
| 24 | 13.23 | 2.65–2.61 (m, 1H) *partially coalescing with H-7β) |
| 25 | 9.36, 9.34 | 1.13–1.05 (m, 4H) *coalescing with H-21 |
| TAa | 173.20 | – |
| TAa | 72.06 | 4.27 (s, ~1.4 H)b |
a
TA, tartaric acid.
b
Integration of the TA singlet after three separate analyses gave 1CP-LSD: TA integration ratios of 1.00:1.00, 1.00:0.98, and 1.00:1.39, respectively (Supporting Information).