TABLE 4

NMR spectroscopic data for vabicaserin and its metabolites

Metabolite1H NMR (600 or 500 MHz, DMSO-d6) δ ppm13C NMR δ ppm
Vabicaserin9.77 (1H, br. s.), 8.81 (1H, br. s.), 7.22 (1H, d, J=7.45 Hz), 7.16 (1H, d, J=7.45 Hz), 6.90 (1H, t, J=7.45 Hz), 4.18 (1H, d, J=13.70 Hz), 4.04 (1H, d, J=13.70 Hz), 3.39 (1H, dd, J=11.59, 4.33 Hz), 3.13 (3H, m), 3.04 (1H, dd, J=12.89, 4.43 Hz), 2.93 (1H, ddd, J=10.98, 7.56, 7.45 Hz), 2.64 (1H, t, J=12.89 Hz), 2.23 (1H, ddd, J=11.99, 8.06, 3.73 Hz), 2.18 (1H, m), 1.99 (1H, td, J=12.89, 9.77 Hz), 1.64 (1H, m), 1.54 (1H, m, J=10.23, 10.10, 10.10, 2.42 Hz), 1.33 (1H, dd, J=11.89, 7.86 Hz), 1.25 (1H, m)147.07, 131.57, 130.85, 128.66, 124.73, 121.03, 55.44, 51.94, 48.95, 46.98, 40.79, 34.1, 31.42, 28.81, 23.31
P17.06 (1H, dd), 7.01 (1H, dd, J=6.75, 0.50 Hz), 6.81 (1H, t, J=7.45 Hz), 4.67 (1H, d, J=4.84 Hz), 4.15 (1H, t, J=8.06 Hz), 3.92 (1H, m), 3.85 (1H, m), 3.18 (1H, d, J=13.50 Hz), 3.05 (1H, m), 2.95 (1H, m), 2.89 (1H, m), 2.83 (1H, t, J=12.59 Hz), 2.37 (1H, dd, J=6.65, 5.24 Hz), 2.19 (2H, m), 1.35 (1H, td, J=12.14, 8.97 Hz), 1.08 (1H, ddd, J=12.54, 6.60, 2.82 Hz).147.15, 131.15, 130.03, 129.12, 127.03, 120.50, 70.19, 56.56, 54.89, 51.30, 48.99, 42.67, 38.12, 37.76, 30.50
P27.07 (1H, d, J=7.66 Hz), 6.98 (1H, d, J=7.45 Hz), 6.81 (1H, t, J=7.35 Hz), 4.53 (1H, d, J=1.01 Hz), 4.10 (1H, dd, J=10.88, 5.24 Hz), 3.89 (1H, d, J=14.51 Hz), 3.81 (1H, d, J=13.70 Hz), 3.39 (1H, d, J=8.46 Hz), 3.18 (1H, d, J=1.41 Hz), 3.02 (1H, d, J=3.83 Hz), 2.99 (1H, m), 2.92 (2H, m), 2.55 (1H, t, J=12.89 Hz), 2.32 (1H, tt, J=8.26, 4.03 Hz), 2.09 (1H, dd, J=13.20, 6.95 Hz), 1.89 (1H, dd, J=14.51, 7.05 Hz), 1.46 (2H, m)147.33, 131.37, 130.38, 128.96, 126.79, 120.49, 69.56, 56.06, 55.24, 51.66, 49.33, 43.03, 39.29, 37.71, 30.19
P38.21 (1H, br. s.), 7.05 (1H, d, J=7.45 Hz), 6.94 (1H, d, J=7.05 Hz), 6.78 (1H, t, J=7.45 Hz), 4.71 (1H, br. s.), 3.81 (1H, br. s.), 3.81 (1H, d, J=12.49 Hz), 3.77 (1H, d, J=13.30 Hz), 3.18 (1H, m), 3.12 (1H, d, J=9.47 Hz), 3.08 (1H, dd, J=13.20, 4.13 Hz), 2.99 (1H, m), 2.91 (1H, m, J=10.48, 10.48, 10.38, 10.17 Hz), 2.61 (1H, t, J=12.59 Hz), 2.27 (1H, ddd, J=8.21, 3.98, 3.73 Hz), 2.03 (1H, m), 1.90 (1H, m), 1.48 (1H, dddd, J=17.73, 8.16, 4.73, 4.63 Hz), 1.35 (1H, m, J=12.95, 9.37, 9.09, 9.09 Hz)128.74, 126.62, 120.46, 75.41, 56.21, 53.4, 52.11, 49.71, 41.96, 38.27, 33.36, 32.19
P47.36 (1H, dt, J=7.66, 0.91 Hz), 6.98 (1H, dd, J=6.35, 0.91 Hz), 6.81 (1H, t, J=7.45 Hz), 4.73 (1H, s), 3.81 (1H, d, J=14.10 Hz), 3.78 (1H, d, J=13.70 Hz), 3.16 (1H, dd, J=2.82, 1.41 Hz), 3.04 (1H, m), 2.99 (1H, dd, J=13.80, 4.73 Hz), 2.91 (1H, t, J=9.87 Hz), 2.81 (1H, dd, J=13.70, 11.89 Hz), 2.16 (1H, dd, J=11.59, 3.53 Hz), 2.04 (1H, m), 1.98 (1H, ddd, J=12.59, 8.26, 1.91 Hz), 1.76 (1H, m), 1.68 (1H, dd, J=12.59, 8.76 Hz), 1.52 (1H, ddd, J=8.21, 3.98, 3.73 Hz), 1.21 (1H, m)146.52, 134.92, 130.96, 127.68, 127.15, 120.29, 78.39, 57.69, 56.45, 52.00, 49.42, 40.56, 40.03, 27.36, 21.02
P57.71 (1H, s), 7.06 (1H, d, J=7.25 Hz), 7.04 (1H, d, J=7.66 Hz), 6.67 (1H, t, J=7.56 Hz), 4.12 (1H, dt, J=15.72, 4.63 Hz), 4.02 (1H, dt, J=15.72, 4.43 Hz), 3.50 (2H, m), 3.12 (1H, dd, J=12.09, 5.24 Hz), 2.94 (1H, dd, J=17.73, 7.66 Hz), 2.83 (1H, dd, J=11.89, 10.48 Hz), 2.28 (1H, m), 2.13 (1H, m), 1.92 (1H, m), 1.62 (1H, m, J=16.22, 8.11, 8.11, 4.43 Hz), 1.52 (1H, dddd, J=19.90, 10.17, 10.02, 3.02 Hz), 1.42 (1H, m), 1.36 (1H, m)144.39, 136.92, 130.05, 130.05, 128.83, 117.4, 115.35, 64.93, 53.15, 51.22, 40.49, 34.61, 34.47, 28.67, 22.34
P68.66 (1H, s), 7.58 (1H, dd, J=8.16, 1.31 Hz), 7.47 (1H, d, J=7.05 Hz), 6.81 (1H, dd, J=7.96, 7.15 Hz), 3.94 (1H, m), 3.86 (1H, m), 3.59 (2H, d, J=3.63 Hz), 3.40 (1H, dd, J=5.04, 2.62 Hz), 3.16 (1H, d, J=1.81 Hz), 3.02 (1H, m), 2.31 (1H, m), 2.11 (1H, dddd), 1.93 (1H, dddd, J=12.87, 5.54, 5.36, 1.81 Hz), 1.66 (1H, m), 1.59 (1H, m), 1.46 (1H, dd, J=12.49, 10.48 Hz), 1.41 (1H, m)164.67, 150.06, 137.87, 137.03, 128.61, 116.78, 111.18, 54.11, 52.95, 51.28, 40.46, 33.87, 33.74, 27.97, 21.59
P79.10, 8.62, 7.35, 7.23, 7.01, 4.18, 4.15, 3.47, 3.34, 3.16 (dd), 3.20, 3.06, 3.01 (t), 2.59, 2.53, 2.32, 2.14, 1.76NA
P99.11, 8.55, 6.94, 6.91, 4.95, 4.18, 4.11, 3.84, 3.37, 3.02, 3.01, 2.93, 2.62, 2.24, 2.19, 2.00, 1.63, 1.52, 1.32, 1.23NA
P109.10, 8.62, 7.23, 7.15, 6.91, 4.29, 4.17, 4.14, 3.34, 3.23, 3.22, 3.20, 3.15, 3.14, 2.68, 2.40, 2.26, 1.97, 1.67, 1.33NA

  • NA, not available.