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. Author manuscript; available in PMC: 2017 Sep 5.
Published in final edited form as: J Med Chem. 2009 Dec 10;52(23):7463–7472. doi: 10.1021/jm900756t

Table 1.

Comparison of Inhibition of Agonist Stimulated [35S]GTPγS Binding in Cloned Human μ, δ, and κ-opioid Receptors for Compounds 8a–d to 3 and 1a

graphic file with name nihms901304u1.jpg
compd R1 R2 R3 R4 R5 μ, DAMGO Ke (nM) δ, DPDPE Ke (nM) κ, U69,593 Ke (nM) μ/κ δ/κ
1 26±7 29±8 0.05±0.02 520 580
3 H H H H H 25.1±3.5b 76.4±2.7b 0.02±0.01b 1255 3830
8a H H CH3 H H 3±1c 24±4c 0.03±0.02c 100 800
8b CH3 H H H H 51.4±15c 118±45c 0.06±0.01c 857 1970
8c H H H H CH3 210±60 491±120 0.16±0.06 1313 3070
8d H CH3 H H H 24±8 21.2±5 0.037±0.003 649 573
8e H H H CH3 H 3.6±1 854±210 0.03±0.008 120 28500
8f H CH3 CH3 H H 5.1±2 1170±400 0.96±0.4 5 1220
8g CH3 H H CH3 H 3.8±1.1 36.8±6.9 0.93±0.05 4 40
8h H CH3 H CH3 H 123±30 2200±900 0.26±0.1 473 8500
8i H H CH3 CH3 H 8.7±2.7 149±13 0.11±0.01 79 1350
8j H H CH3 H CH3 7.2±1.8 132±24 0.11±0.03 66 1200
8k H CH3 H H CH3 880±220 2300±900 4.3±2.7 204 535
8l CH3 CH3 H CH3 H 1450±490 IAd 15.2±3.7 95
8m CH3 H CH3 CH3 H 17.5±3.6 18.7±1.5 3.5±0.8 5 5
8n H CH3 CH3 CH3 H 59.1±16 2100±600 0.52±0.2 114 4040
8o CH3 H H CH3 CH3 7.0±1.4 117±30 2.2±0.6 3 53
8p H CH3 CH3 H CH3 360±120 IAd 2.03±0.03 180
a

The data represent the means ± SE from at least three independent experiments.

b

The Ke values for 3 supplied by the NIDA Opioid Treatment Discovery Program (OTDP) were 3.41, 79.3, and 0.01 nM for the μ, δ, and κ receptors, respectively (ref 14).

c

Data taken from ref 23.

d

Inactive or >10000 nM.