Table 2
Effects of side chain length and substitutions in the terminal carbon on receptor affinity and pharmacological potency
| No.2-a | Chemical Name | R | KD | ED50 | |
|---|---|---|---|---|---|
| SA | TF | RT | |||
| nM | mg/kg | ||||
| 18 | 3-(1,6-Heptadiynyl-Δ8-THC | 460 ± 79 | 31 | 37 | |
| O-1021 | 12 (30) | 57 (30) | –2.9 (30) | ||
| 19 | 3-(5-Cyano-1-pentynyl)-Δ8-THC | 104 ± 12 | 33.6 | 15.1 | |
| O-1068 | 34 (60) | 53 (60) | –4.3 (60) | ||
| 20 | 3-(3-Carbomethoxy-2-propynyl)-Δ8-THC | 731 ± 139 | |||
| O-1351 | 29 (30) | 31 (30) | –1.6 (30) | ||
| 21 | 3-(4-Bromo-2-butynyl)-Δ8-THC | 143 ± 31 | |||
| O-1187 | 60 (30) | 38 (30) | –2.6 (30) | ||
| 22 | 3-(5-Bromo-2-pentynyl)-Δ8-THC | 25 ± 4.2 | 14.1 | 23.7 | 11.4 |
| O-1105 | 63 (60) | 52 (30) | –4.2 (60) | ||
| 23 | 3-(5-Hydroxy-2-pentynyl)-Δ8-THC | 448 ± 75 | 3.77 | 22.8 | |
| O-1359 | 91 (30) | 25 (30) | –3.1 (30) | ||
| 24 | 3-(5-Cyano-2-pentynyl)-Δ8-THC | 31 ± 8.3 | |||
| O-1106 | 45 (60) | 53 (60) | –3.3 (60) | ||
| 25 | 3-(5-Azido-2-pentynyl)-Δ8-THC | 6.15 ± 0.44 | 1.54 | 7.56 | 2.76 |
| O-1355 | 82 (30) | 53 (10) | –4.5 (10) | ||
| 26 | 3-(5-Acetamido-2-pentynyl)-Δ8-THC | 307 ± 24 | 4.69 | 30.2 | |
| O-1356 | 71 (30) | 46 (30) | –3.2 (30) | ||
| 27 | 3-(6-Nitro-2-hexynyl)-Δ8-THC | 5.34 ± 0.75 | |||
| O-1358 | 50 (30) | 14 (30) | –3.0 (30) | ||
| 28 | 3-(4-Carbomethoxy-3-butynyl)-Δ8-THC | >10,000 | |||
| O-1357 | 61 (30) | 41 (30) | –3.2 (30) | ||
Spontaneous activity (SA), tail-flick response (TF), and rectal temperature (RT) are expressed as ED50 values (mg/kg). A blank space indicates that calculation of an ED50 was not possible. The maximal effect with the dose in parentheses is given under the ED50 value. The KD values represent means ± S.E. of at least three separate experiments.
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↵2-a Listed below the boldface analog number is the reference number assigned by either Organix, Inc. (O) or Dr. Huffman (J.W.H.).