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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 1.

[3H] Opioid receptor binding dataa for ortho-a and para-a isomers 1, 5, 6, and 10 and for ortho-b and para-b enantiomers 16a, 16b, 19a, and 19b

graphic file with name nihms307538u1.jpg
Ki (nM)
Cmpd R1 R2 R3 μb δc κd
rac 1 OH H Me > 2800 > 4900 7500 ± 1029
rac 5 OH H PhEt 167 ± 14 > 4900 171 ± 14
rac 6 H OH Me > 2800 > 4900 > 8600
rac 10 H OH PhEt 486 ± 39 > 4900 98 ± 5
16a: (+)-4R,6aS,11bR H OH PhEt 250 ± 28 > 5,000 199 ± 10
16b: (−)-4S,6aR,11bS H OH PhEt 352 ± 28 > 5,000 102 ± 3
19a: (−)-4S,6aR,11bS OH H PhEt 384 ± 38 > 5,000 367 ± 19
19b: (+)-4R,6aS,11bR OH H PhEt 49 ± 3 > 5,000 42 ± 1.8
Morphine 2.55 ± 0.01
a

Assays were conducted15 using CHO cells, which were stably transfected and express the μ-, δ- or κ-opiate receptors respectively. All results n=3.