Table 1.

Binding Data for 4- or 5-substituted analogues of 1^a

Compd	Struc ture	R	SERT Ki ± SEM (nM)	NET Ki ± SEM (nM)	Ki(NET)/Ki (SERT)
1b	A	CN	1.94±0.198	5950±77.4	3070
S-1b	A	CN	0.89±0.132	10500±893	11800
2	A	COOCH3	4.17±0.482	64.3%e	>1000
3c	A	CONH2	17.7±1.80	123±17.7	7
4d	A	CHO	4.3±0.096	46.1% e	>1000
5	A	CH2NH2	41.9±5.73	33.2% e	>1000
6	C		18.9±0.793	29.3% e	>1000
7	C		13.6±1.87	>80000	5882
8	C		3.24±0.328	11100±1490	3426
9	C		7.95±1.07	39.7% e	>1000
10	C		22.7±2.62	19.7% e	>1000
11	D		11. 0± 1.64	284±19.0	26
12	D		11.3±1.19	683±40.3	60
13	D		8.3±0.537	653±86.5	79
14	D		23.6±1.54	2330±331	99
15	D		19.7±2.80	66.9% e	>100
16	C	CH2N(CH3)2	32.1±1.24	21.9% e	>1000
17b,d	A	Br	1.04±0.126	28400 (global fit no SEM)	>10,000
19	A		18.6±1.65	8280±825	227
20	A		29.2±4.11	42% e	>10,000
21	A		21.0±1.72	4750±860	226
22	B	I	7.05±0.404	11300±867	1603
61b	A		10.4±1.34	3820±318	367
62b	A		9.32±1.36	11400±1090	1223
63b	A	I	1.42±0.155	32500± 4630	>10,000

^aThese novel analogues were assessed by radioligand binding displacement of [³H]1 (for SERT) and [³H]nisoxetine (for NET) in rat brain stem and frontal cortex, respectively.³⁵

^bPublished compound.⁸

^cPublished compound.³⁰

^dPublished compound.^4,7,30

^e% Displacement at 10 µM.