Abstract
A series of 3-arylnortrop-2-enes and 3α-arylmethoxy-3β-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (
6e
) exhibited high affinity for the SERT (
K
i
= 0.3 nM). The 3α-arylmethoxy-3β-arylnortropanes were generally SERT selective with the 3α-(3.4-dichlorophenylmethoxy)-3β̃phenylnortrop-2-ene (
7c
) possessing subnanomolar potency (
K
i
= 0.061 nM). However, 3α-(3,4-dichlorophenylmethoxy)-3β-phenylnortrop-2-ene (
7b
) exhibited high affinity at all three transporters [(DAT
K
i
= 22 nM), (SERT
K
i
= 6 nM ) and (NET
K
i
= 101 nM)].
