. Author manuscript; available in PMC: 2011 Aug 26.

Published in final edited form as: J Med Chem. 2010 Aug 26;53(16):6112–6121. doi: 10.1021/jm1005034

Table 2.

In Vitro Data for (±)1 and its chiral analogues^a



compound	R’	SERT Ki ± SEM (nM)	NET Ki ± SEM (nM)	DAT Ki ± SEM (nM)	Ki(NET)/Ki (SERT)	Ki(DAT)/Ki (SERT)
(±)-1	CN	1.94 ± 0.198	5950 ± 77.4	9270 ± 872	3070	4780
S(+)-1	CN	0.89 ± 0.132	10500 ± 893	8150 ± 314	11800	9160
R(−)-1	CN	28.3 ± 3.62	4980 ± 515	7980±646	178	282
(±)-5^b	Br	1.04 ± 0.126	28400 (global fit no SEM)	1650 ± 112	>10,000	1590
S(+)-5	Br	0.92 ± 0.056	8410 ± 202	2250 ± 115	9140	2450
R(−)-5	Br	23.6 ± 1.76	21600 ± 3210	1350 ± 44	915	57
(±)-9	Ph-CH=CH	9.32 ± 1.36	11400 ± 1090	836 ± 14.9	1220	90
S(+)-9	Ph-CH=CH	10.6 ± 1.09	16800 ± 1360	1810 ± 46.8	1590	171
R(−)-9	Ph-CH=CH	113 ± 14.7	5190 ± 427	541 ± 40.7	46	4.79

These novel analogues were assessed by radioligand binding displacement of [³H]citalopram (for SERT), [³H]nisoxetine (for NET) and [³H]WIN 35, 428 in rat brain stem, frontal cortex and caudate-putamen, respectively.³⁶

Published compound.³²