TABLE 1.

Chromatographic, mass spectral, and proton NMR data for amoxapine and its metabolites formed by C. elegans

Compound	HPLC retention time (min)	Mass spectral ions (m/z)a	NMR chemical shifts (ppm)b
7-Hydroxyamoxapinec	17.9	329 (24), 299, 285, 273, 261 (100), 244, 209, 85, 69, 56 (7)	7.37 (H1), 7.44 (H3), 7.19 (H4), 6.64 (H6), 6.60 (H8), 7.00 (H9), 3.40, 3.47 (Ha-d)
N-Formyl-7-hydroxyamoxapinec	21.8	357 (100), 328, 313, 299, 285, 273 (57), 260, 245, 209, 113 (7), 98 (4), 85, 70, 56 (5)	7.38 (H1), 7.45 (H3), 7.20 (H4), 6.65 (H6), 6.61 (H8), 7.02 (H9), 8.08 (H10), 3.43, 3.50, 3.64 (Ha-d)
N-Formylamoxapined	29.1	341 (100), 312, 283, 268/270, 257 (84), 244, 228, 229, 193, 113 (7), 98, 85, 69, 56 (6)	7.37 (H1), 7.47 (H3), 7.25 (H4), 7.06, 7.10–7.15 (H6-9), 8.09 (H10), 3.52, 3.65 (Ha-d)
Amoxapined	26.7	313 (10), 283, 263, 257, 245 (100), 228, 216, 193, 56 (4)	7.33 (H1), 7.45 (H3), 7.22 (H4), 7.30, 7.07–7.15 (H6-9), 3.34, 3.86 (Ha-d)

^aIons above m/z 209 had an isotope pattern consistent with the presence of a single chlorine. Only the most abundant ion is shown. The numbers in parentheses are relative abundance values, expressed as percentages. 

^bSamples were dissolved in methylene-d₂-chloride. 

^cThe coupling constants were as follows: J_1,3 = 2.6 Hz; J_3,4 = 8.8 Hz; J_6,8 = 2.8 Hz; and J_8,9 = 8.6 Hz. 

^dThe coupling constants were as follows: J_1,3 = 2.6 Hz; and J_3,4 = 8.6 Hz.