Table 1.

Binding affinities of racemic and enantiomeric compounds 5–7 for VAChT, σ₁,and σ₂ receptors

Entry	Compound	Ki, nM a			σ1/VAChT	σ2/VAChT	log P b
		VAChT	σ1	σ2
1	(±)-5c	38.0 ± 3.8	2120 ± 50	1860 ± 140	56	49	2.87
	(+)-5	396 ± 120	7380 ± 1240	3410 ± 270	19	9
	(−)-5	17.0 ± 1.8	7360 ± 710	4970 ± 180	433	292
2	(±)-6d	1.74 ± 0.32	13.2 ± 0.2	1890 ± 240	8	1086	3.15
	(+)-6	4.35 ± 0.51	24.7 ± 3.9	2960 ± 410	6	680
	(−)-6	0.37 ± 0.04	7.23 ± 0.36	5840 ± 770	20	15784
3	(±)-7	2.68 ± 0.23	---	---	---	---	2.91
	(+)-7	2.31 ±0.20	1250 ± 70	>10,000	541	4329
	(−)-7	0.31 ±0.03	1870 ± 250	5480 ± 140	6032	17677

^aK_i values (mean ± SEM) were determined in three independent experiments.

^bCalculated value at pH 7.4 with ACD/ILab, version 7.0 (Advanced Chemistry Development, Inc., Canada).

^cReference 20,

^dReference 23.