Table 1.

IC₅₀ Values of 1 Analogues in Nanomolar, Determined by Cellular Ca²⁺ Flux Assays in HEK-293 Cells Stably Expressing hTRPM8 and Represented as Mean ± SEM from Three Independent Experiments^a

		Functional Activity
Cmpd	R1	hTRPM8 potcncy IC50 ± SEM
1		16 ± 1 μM
2		468 ± 1 nM
3		49 ± 1 μM
4		7.1 ±0.9 μM
5		52 ± 1 nM
6		692 ± 1 nM
7		62 ± 1 nM
8		21 ± 1 μM
9		55 + 1 μM
10 (diastereomeric mixture)		6± 1 nM
11		52 ± 1 nM
12 (isolated diastereomer)		1.4 ± 1.0 nM
13		40 ± 1 nM
14		2.4 ± 1.0 nM
15		16 ± 1 nM
RQ-00203078		3± 1 nM
icilin	EC50	74 ± 3 nM
(−)-menthol	EC50	5.7 ± 0.72 μM

^aIC₅₀ is defined by concentration of the compounds that inhibit 50% of icilin-evoked Ca²⁺ entry.