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. Author manuscript; available in PMC: 2012 Jul 15.
Published in final edited form as: Bioorg Med Chem. 2011 May 24;19(14):4330–4337. doi: 10.1016/j.bmc.2011.05.035

Table 2.

Functional data ([35S]GTP-γ-S) for N-phenethyl-substituted ortho-a and para-a racemates 5 and 10 and for ortho-b and para-b enantiomers 16a, 16b, 19a, and 19b

graphic file with name nihms307538u2.jpg
Ke (nM)a
Cmpd R1 R2 μ-Antagonism κ-Antagonism
rac 5 OH H 274 ± 49 163 ± 29
rac 10 H OH 23 ± 10 46 ± 9
16a: (+)-4R,6aS,11bR H OH 47 ± 9 100 ± 3
16b: (−)-4S,6aR,11bS H OH 227 ± 33 103 ± 17
19a: (−)-4S,6aR,11bS OH H 328 ± 67 761 ± 191
19b: (+)-4R,6aS,11bR OH H 31 ± 6 22 ± 6
Naloxone 2.3 ± 0.3 -
norBNI - 0.11 ± 0.02
a

[35S]GTP-γ-S binding was performed using CHO hMOR cells which express the human μ-opiate receptor, and were conducted as described in section 4.2.1. All values n=3.