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List of JWH cannabinoids

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(Redirected from JWH cannabinoids) Substances synthesized by John W. Huffman's research group

The John W. Huffman research group at Clemson University synthesized over 450 cannabinoids. Some of those are:

Cannabinoids and their Ki values
Name Class Ki / nM at CB1 Ki / nM at CB2 Selectivity Structure
JWH-004 Naphthoylindole 48 ± 13 4 ± 1.5 CB2 (12x)
JWH-007 Naphthoylindole 9.5 ± 4.5 2.9 ± 2.6 CB2 (3.3x)
JWH-009 Naphthoylindole >10000 141 ± 14 CB2 (>70x)
JWH-011 Naphthoylindole
JWH-015 Naphthoylindole 164 ± 22 13.8 ± 4.6 CB2 (12x)
JWH-016 Naphthoylindole 22 ± 1.5 4.3 ± 1.6 CB2 (5.1x)
JWH-018 Naphthoylindole 9 ± 5 2.9 ± 2.6 CB2 (3.1x)
JWH-019 Naphthoylindole 9.8 ± 2 5.55 ± 2 CB2 (1.77x)
JWH-020 Naphthoylindole 128 ± 17 205 ± 20 CB1 (1.6x)
JWH-030 Naphthoylpyrrole 87 ± 3 320 ± 127 CB1 (3.7x)
JWH-031 Naphthoylpyrrole 399 ± 109
JWH-032 Naphthoylpyrrole >10000 >10000 —
JWH-033 Naphthoylpyrrole 666 ± 77
JWH-036 Naphthoylpyrrole 309 ± 11
JWH-042 Naphthoylindole >10000 5050 ± 192 CB2
JWH-043 Naphthoylindole 1180 ± 44 964 ± 242 CB2 (1.2x)
JWH-044 Naphthoylpyrrole >10000 >10000 —
JWH-045 Naphthoylpyrrole >10000 >10000 —
JWH-046 Naphthoylindole 343 ± 38 16.3 ± 4.9 CB2 (21x)
JWH-047 Naphthoylindole 59 ± 3 3.47 ± 1.80 CB2 (17x)
JWH-048 Naphthoylindole 10.7 ± 1.0 0.49 ± 0.13 CB2 (22x)
JWH-049 Naphthoylindole 55.1 ± 17.0 32.3 ± 2.4 CB2 (1.7x)
JWH-050 Naphthoylindole 342 ± 6 526 ± 133 CB1 (1.5x)
JWH-051 Dibenzopyran 1.20 0.03 CB2 (40x)
JWH-056 Dibenzopyran >10000 32 ± 9 CB2
JWH-057 Dibenzopyran 23 ± 7 2.9 ± 1.6 CB2 (8x)
JWH-065 Dibenzopyran 399 ± 76 10 ± 2 CB2 (40x)
JWH-070 Naphthoylindole >10000 >10000
JWH-071 Naphthoylindole 1340 ± 123 2940 ± 852 CB1 (2.2x)
JWH-072 Naphthoylindole 1050 ± 5.5 170 ± 54 CB2 (6x)
JWH-073 Naphthoylindole 8.9 ± 1.8 27 ± 12 CB1 (3x)
JWH-076 Naphthoylindole 214 ± 11 106 ± 46 CB2 (2x)
JWH-077 Naphthoylindole >10000 >10000
JWH-078 Naphthoylindole 817 ± 60 633 ± 116 CB2 (1.3x)
JWH-079 Naphthoylindole 63.0 ± 3.0 32.0 ± 6.0 CB2 (2x)
JWH-080 Naphthoylindole 8.9 ± 1.8 2.21 ± 1.30 CB2 (4x)
JWH-081 Naphthoylindole 1.2 ± 0.03 12.4 ± 2.2 CB1 (10x)
JWH-082 Naphthoylindole 5.3 ± 0.8 6.40 ± 0.94 CB1 (1.2x)
JWH-083 Naphthoylindole 106 ± 12 102 ± 50 —
JWH-091 (Δ-THCP) Dibenzopyran 22.0 ± 3.9
JWH-093 Naphthoylindole 40.7 ± 2.8 59.1 ± 10.5 CB1 (1.45x)
JWH-094 Naphthoylindole 476 ± 67 97.3 ± 2.7 CB2 (4.9x)
JWH-095 Naphthoylindole 140 ± 4.3 312 ± 83 CB1 (2.2x)
JWH-096 Naphthoylindole 33.7 ± 2.9 13.3 ± 5.6 CB2 (2.5x)
JWH-097 Naphthoylindole 455 ± 28 121 ± 15 CB2 (3.8x)
JWH-098 Naphthoylindole 4.5 ± 0.1 1.9 ± 0.3 CB2 (2.4x)
JWH-099 Naphthoylindole 35.3 ± 9.0 17.8 ± 2.9 CB2 (2x)
JWH-100 Naphthoylindole 381 ± 102 155 ± 74 CB2 (2.5x)
JWH-102 Dibenzopyran 7.9 ± 0.9 5.2 ± 2.0 CB2 (1.5x)
JWH-103 Dibenzopyran 28 ± 3 23 ± 7 CB2 (1.2x)
JWH-116 Naphthoylindole 52 ± 5
JWH-120 Naphthoylindole 1054 ± 31 6.1 ± 0.7 CB2 (173x)
JWH-122 Naphthoylindole 0.69 ± 0.05 1.2 ± 1.2 —
JWH-124 (Δ-Parahexyl) Dibenzopyran 41.0 ± 3.8
JWH-130 (Δ-THCB) Dibenzopyran 65.0 ± 13
JWH-133 Dibenzopyran 677 ± 132 3.4 ± 1.0 CB2 (200x)
JWH-138 Dibenzopyran 8.5 ± 1.4
JWH-139 Dibenzopyran 2290 ± 505 14 ± 10 CB2 (164x)
JWH-142 Dibenzopyran 529 ± 49 35 ± 14 CB2 (15x)
JWH-143 Dibenzopyran 924 ± 104 65 ± 8 CB2 (14x)
JWH-145 Naphthoylpyrrole 14 ± 2 6.4 ± 0.4 CB2 (2.2x)
JWH-146 Naphthoylpyrrole 21 ± 2 62 ± 5 CB2 (3.0x)
JWH-147 Naphthoylpyrrole 11 ± 1 7.1 ± 0.2 CB2 (1.5x)
JWH-148 Naphthoylindole 123 ± 8 14.0 ± 1.0 CB2 (8x)
JWH-149 Naphthoylindole 5.0 ± 2.1 0.73 ± 0.03 CB2 (6.8x)
JWH-150 Naphthoylpyrrole 60 ± 1 15 ± 2 CB2 (4x)
JWH-151 Naphthoylindole >10000 30 ± 1.1 CB2 (>333x)
JWH-153 Naphthoylindole 250 ± 24 11 ± 0.5 CB2 (23x)
JWH-156 Naphthoylpyrrole 404 ± 18 104 ± 18 CB2 (4x)
JWH-159 Naphthoylindole 45 ± 1 10.4 ± 1.4 CB2 (4.3x)
JWH-160 Naphthoylindole 1568 ± 201 441 ± 110 CB2 (3.6x)
JWH-161 Dibenzopyran hybrid 19.0
JWH-163 Naphthoylindole 2358 ± 215 138 ± 12 CB2 (17x)
JWH-164 Naphthoylindole 6.6 ± 0.7 6.9 ± 0.2 —
JWH-165 Naphthoylindole 204 ± 26 71 ± 8 CB2 (2.9x)
JWH-166 Naphthoylindole 44 ± 10 1.9 ± 0.08 CB2 (23x)
JWH-167 Phenylacetylindole 90 ± 17 159 ± 14 CB1 (1.77x)
JWH-171 Hydrocarbon 51
JWH-175 Naphthylmethylindole 22 ± 2
JWH-176 Hydrocarbon 26 ± 4
JWH-180 Naphthoylindole 26 ± 2 9.6 ± 2.0 CB2 (2.7x)
JWH-181 Naphthoylindole 1.3 ± 0.1 0.62 ± 0.04 CB2 (2.1x)
JWH-182 Naphthoylindole 0.65 ± 0.03 1.1 ± 0.1 CB1 (1.7x)
JWH-184 Naphthylmethylindole 23 ± 6
JWH-185 Naphthylmethylindole 17 ± 3
JWH-186 Dibenzopyran 187 ± 23 5.6 ± 1.7 CB2 (33x)
JWH-187 Dibenzopyran 84 ± 16 3.4 ± 0.5 CB2 (25x)
JWH-188 Dibenzopyran 270 ± 58 18 ± 2 CB2 (15x)
JWH-189 Naphthoylindole 52 ± 2 12 ± 0.8 CB2 (4.3x)
JWH-190 Dibenzopyran 8.8 ± 1.4 1.6 ± 0.03 CB2 (5.5x)
JWH-191 Dibenzopyran 1.8 ± 0.3 0.52 ± 0.03 CB2 (3.5x)
JWH-192 Naphthylmethylindole 41 ± 13
JWH-193 Naphthoylindole 6 ± 1
JWH-194 Naphthylmethylindole 127 ± 19
JWH-195 Naphthylmethylindole 113 ± 28
JWH-196 Naphthylmethylindole 151 ± 18
JWH-197 Naphthylmethylindole 323 ± 98
JWH-198 Naphthoylindole 10 ± 2
JWH-199 Naphthylmethylindole 20 ± 2
JWH-200 Naphthoylindole 42 ± 5
JWH-201 Phenylacetylindole 1064 ± 21 444 ± 14 CB2 (2.4x)
JWH-202 Phenylacetylindole 1678 ± 63 645 ± 6 CB2 (2.6x)
JWH-203 Phenylacetylindole 8.0 ± 0.9 7.0 ± 1.3 —
JWH-204 Phenylacetylindole 13 ± 1 25 ± 1 CB1 (1.9x)
JWH-205 Phenylacetylindole 124 ± 23 180 ± 9 CB1 (1.45x)
JWH-206 Phenylacetylindole 389 ± 25 498 ± 37 CB1 (1.28x)
JWH-207 Phenylacetylindole 1598 ± 134 3723 ± 10 CB1 (2.33x)
JWH-208 Phenylacetylindole 179 ± 7 570 ± 127 CB1 (3.18x)
JWH-209 Phenylacetylindole 746 ± 49 1353 ± 270 CB1 (1.81x)
JWH-210 Naphthoylindole 0.46 ± 0.03 0.69 ± 0.01 CB1 (1.5x)
JWH-211 Naphthoylindole 70 ± 0.8 12 ± 0.8 CB2 (5.8x)
JWH-212 Naphthoylindole 33 ± 0.9 10 ± 1.2 CB2 (3.3x)
JWH-213 Naphthoylindole 1.5 ± 0.2 0.42 ± 0.05 CB2 (3.6x)
JWH-215 Dibenzopyran 1008 ± 117 85 ± 21 CB2 (12x)
JWH-216 Dibenzopyran 1856 ± 148 333 ± 104 CB2 (5.6x)
JWH-217 Dibenzopyran >10000 1404 ± 66 CB2 (>7x)
JWH-220 Hydrocarbon 19
JWH-224 Dibenzopyran 347 ± 34 28 ± 1 CB2 (12.3x)
JWH-225 Dibenzopyran >10000 325 ± 70 CB2 (>31x)
JWH-226 Dibenzopyran 4001 ± 282 43 ± 3 CB2 (93x)
JWH-227 Dibenzopyran 40 ± 6 4.4 ± 0.3 CB2 (9x)
JWH-229 Dibenzopyran 3134 ± 110 18 ± 2 CB2 (174x)
JWH-230 Dibenzopyran 15 ± 3 1.4 ± 0.12 CB2 (10.7x)
JWH-233 Dibenzopyran 14 ± 3 1.0 ± 0.3 CB2 (14x)
JWH-234 Naphthoylindole 8.4 ± 1.8 3.8 ± 0.6 CB2 (2.2x)
JWH-235 Naphthoylindole 338 ± 34 123 ± 34 CB2 (2.7x)
JWH-236 Naphthoylindole 1351 ± 204 240 ± 63 CB2 (5.6x)
JWH-237 Phenylacetylindole 38 ± 10 106 ± 2 CB1 (2.8x)
JWH-239 Naphthoylindole 342 ± 20 52 ± 6 CB2 (6.6x)
JWH-240 Naphthoylindole 14 ± 1 7.2 ± 1.3 CB2 (1.9x)
JWH-241 Naphthoylindole 147 ± 20 49 ± 7 CB2 (3.0x)
JWH-242 Naphthoylindole 42 ± 9 6.5 ± 0.3 CB2 (6.5x)
JWH-243 Naphthoylpyrrole 285 ± 40 41 ± 3 CB2 (6.95x)
JWH-244 Naphthoylpyrrole 130 ± 6 18 ± 1 CB2 (7.22x)
JWH-245 Naphthoylpyrrole 276 ± 4 25 ± 2 CB2 (11x)
JWH-246 Naphthoylpyrrole 70 ± 4 16 ± 1 CB2 (4.38x)
JWH-247 Dibenzopyran 427 ± 31 99 ± 4 CB2 (4.3x)
JWH-248 Phenylacetylindole 1028 ± 39 657 ± 19 CB2 (1.56x)
JWH-249 Phenylacetylindole 8.4 ± 1.8 20 ± 2 CB1 (2.38x)
JWH-250 Phenylacetylindole 11 ± 2 33 ± 2 CB1 (3x)
JWH-251 Phenylacetylindole 29 ± 3 146 ± 36 CB2 (5x)
JWH-252 Phenylacetylindole 23 ± 3 19 ± 1 CB2 (1.2x)
JWH-253 Phenylacetylindole 62 ± 10 84 ± 12 CB1 (1.35x)
JWH-254 Dibenzopyran 4724 ± 509 319 ± 16 CB2 (14.8x)
JWH-256 Dibenzopyran 4300 ± 888 97 ± 18 CB2 (44x)
JWH-258 Naphthoylindole 4.6 ± 0.6 10.5 ± 1.3 CB1 (2.3x)
JWH-259 Naphthoylindole 220 ± 29 74 ± 7 CB2 (3.0x)
JWH-260 Naphthoylindole 29 ± 0.4 25 ± 1.9 CB2 (1.2x)
JWH-261 Naphthoylindole 767 ± 105 221 ± 14 CB2 (3.5x)
JWH-262 Naphthoylindole 28 ± 3 5.6 ± 0.7 CB2 (5.0x)
JWH-265 Naphthoylindole 3788 ± 323 80 ± 13 CB2 (47x)
JWH-266 Naphthoylindole >10000 455 ± 55 CB2 (>22x)
JWH-267 Naphthoylindole 381 ± 16 7.2 ± 0.14 CB2 (53x)
JWH-268 Naphthoylindole 1379 ± 193 40 ± 0.6 CB2 (34x)
JWH-277 Dibenzopyran 3905 ± 91 589 ± 65 CB2 (6.6x)
JWH-278 Dibenzopyran 906 ± 80 69 ± 6 CB2 (13x)
JWH-292 Naphthoylpyrrole 29 ± 1 20 ± 1 CB2 (1.45x)
JWH-293 Naphthoylpyrrole 100 ± 5 41 ± 4 CB2 (2.44x)
JWH-298 Dibenzopyran 812 ± 67 198 ± 23 CB2 (4.1x)
JWH-299 Dibenzopyran 415 ± 50 30 ± 2 CB2 (13.8x)
JWH-300 Dibenzopyran 118 ± 16 5.3 ± 0.1 CB2 (22x)
JWH-301 Dibenzopyran 295 ± 64 48 ± 4 CB2 (6.1x)
JWH-302 Phenylacetylindole 17 ± 2 89 ± 15 CB1 (5.26x)
JWH-303 Phenylacetylindole 117 ± 10 138 ± 12 CB1 (1.18x)
JWH-304 Phenylacetylindole 3363 ± 332 2679 ± 688 CB2 (1.26x)
JWH-305 Phenylacetylindole 15 ± 1.8 29 ± 5 CB1 (1.93x)
JWH-306 Phenylacetylindole 25 ± 1 82 ± 11 CB1 (3.28x)
JWH-307 Naphthoylpyrrole 7.7 ± 1.8 3.3 ± 0.2 CB2 (2.33x)
JWH-308 Naphthoylpyrrole 41 ± 1 33 ± 2 CB2 (1.24x)
JWH-309 Naphthoylpyrrole 41 ± 3 49 ± 7 CB1 (1.20x)
JWH-310 Dibenzopyran 1059 ± 51 36 ± 3 CB2 (29x)
JWH-311 Phenylacetylindole 23 ± 2 39 ± 3 CB1 (1.70x)
JWH-312 Phenylacetylindole 72 ± 7 91 ± 20 CB1 (1.26x)
JWH-313 Phenylacetylindole 422 ± 19 365 ± 92 CB2 (1.16x)
JWH-314 Phenylacetylindole 39 ± 2 76 ± 4 CB1 (1.95x)
JWH-315 Phenylacetylindole 430 ± 24 182 ± 23 CB2 (3.36x)
JWH-316 Phenylacetylindole 2862 ± 670 781 ± 105 CB2 (3.66x)
JWH-336 Dibenzopyran 4589 ± 367 153 ± 15 CB2 (30x)
JWH-338 Dibenzopyran >10000 111 ± 16 CB2 (>90x)
JWH-339 Dibenzopyran >10000 2317 ± 93 CB2 (>4.3x)
JWH-340 Dibenzopyran 135 ± 6 30 ± 1 CB2 (4.5x)
JWH-341 Dibenzopyran 100 ± 8 10 ± 0.1 CB2 (10x)
JWH-346 Naphthoylpyrrole 67 ± 6 39 ± 2 CB2 (1.72x)
JWH-347 Naphthoylpyrrole 333 ± 17 169 ± 17 CB2 (1.97x)
JWH-348 Naphthoylpyrrole 218 ± 19 53 ± 1 CB2 (4.11x)
JWH-349 Dibenzopyran 376 ± 1 38 ± 4 CB2 (9.9x)
JWH-350 Dibenzopyran 395 ± 50 12 ± 1 CB2 (33x)
JWH-351 Dibenzopyran >10000 295 ± 3 CB2 (>34x)
JWH-352 Dibenzopyran >10000 47 ± 2 CB2 (>213x)
JWH-353 Dibenzopyran 1493 ± 10 31 ± 1 CB2 (48x)
JWH-354 Dibenzopyran 1961 ± 21 241 ± 14 CB2 (8.1x)
JWH-355 Dibenzopyran 2162 ± 220 108 ± 17 CB2 (20x)
JWH-356 Dibenzopyran 5837 ± 701 108 ± 17 CB2 (54x)
JWH-357 Dibenzopyran 647 ± 78 185 ± 4 CB2 (3.5x)
JWH-358 Dibenzopyran 1243 ± 266 52 ± 3 CB2 (24x)
JWH-359 Dibenzopyran 2918 ± 450 13.0 ± 0.2 CB2 (220x)
JWH-360 Dibenzopyran 2449 ± 606 160 ± 8 CB2 (15x)
JWH-361 Dibenzopyran 63 ± 3 2.7 ± 0.1 CB2 (23x)
JWH-362 Dibenzopyran 127 ± 8 34 ± 5 CB2 (3.7x)
JWH-363 Naphthoylpyrrole 245 ± 5 71 ± 1 CB2 (3.45x)
JWH-364 Naphthoylpyrrole 34 ± 3 29 ± 1 CB2 (1.17x)
JWH-365 Naphthoylpyrrole 17 ± 1 3.4 ± 0.2 CB2 (5.0x)
JWH-366 Naphthoylpyrrole 191 ± 12 24 ± 1 CB2 (7.96x)
JWH-367 Naphthoylpyrrole 53 ± 2 23 ± 1 CB2 (2.30x)
JWH-368 Naphthoylpyrrole 16 ± 1 9.1 ± 0.7 CB2 (1.76x)
JWH-369 Naphthoylpyrrole 7.9 ± 0.4 5.2 ± 0.3 CB2 (1.52x)
JWH-370 Naphthoylpyrrole 5.6 ± 0.4 4.0 ± 0.5 CB2 (1.40x)
JWH-371 Naphthoylpyrrole 42 ± 1 64 ± 2 CB1 (1.52x)
JWH-372 Naphthoylpyrrole 77 ± 2 8.2 ± 0.2 CB1 (9.39x)
JWH-373 Naphthoylpyrrole 60 ± 3 69 ± 2 CB1 (1.15x)
JWH-387 Naphthoylindole 1.2 ± 0.1 1.1 ± 0.1 —
JWH-398 Naphthoylindole 2.3 ± 0.1 2.8 ± 0.2 CB1 (1.22x)
JWH-416 Naphthoylindole 73 ± 10 3.3 ± 0.1 CB2 (22x)
JWH-417 Naphthoylindole 522 ± 58 13 ± 0.2 CB2 (40x)
JWH-422 Naphthoylindole 501 ± 48 20 ± 0.4 CB2 (25x)
JWH-423 Naphthoylindole 140 ± 10 6.6 ± 0.2 CB2 (21x)
JWH-424 Naphthoylindole 21 ± 3.4 5.4 ± 0.2 CB2 (3.9x)
JWH-425 Naphthoylindole 54 ± 11 10 ± 0.4 CB2 (5.4x)


See also

Notes

  1. Ki is the compound's binding affinity for the cannabinoid receptor type 1 (CB1) or cannabinoid receptor type 2 (CB2).

References

  1. Manera C, Tuccinardi T, Martinelli A (2008). "Indoles and related compounds as cannabinoid ligands". Mini Rev Med Chem. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.
  2. Wiley JL, Marusich JA, Huffman JW (2014). "Moving around the molecule: relationship between chemical structure and in vivo activity of synthetic cannabinoids". Life Sci. 97 (1): 55–63. doi:10.1016/j.lfs.2013.09.011. PMC 3944940. PMID 24071522.
  3. Wiley JL, Marusich JA, Thomas BF (2017). "Combination Chemistry: Structure-Activity Relationships of Novel Psychoactive Cannabinoids". Curr Top Behav Neurosci. Current Topics in Behavioral Neurosciences. 32: 231–248. doi:10.1007/7854_2016_17. ISBN 978-3-319-52442-9. PMID 27753007.
  4. Banister SD, Connor M (2018). "The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonists as New Psychoactive Substances: Origins". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 165–190. doi:10.1007/164_2018_143. ISBN 978-3-030-10560-0. PMID 29980914.
  5. ^ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Thompson AL, Bushell S, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  6. ^ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, Showalter VM, Abood ME, Martin BR (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence. 60 (2): 133–40. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
  7. ^ Huffman JW, Liddle J, Yu S, Aung MM, Abood ME, Wiley JL, Martin BR (December 1999). "3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC and related compounds: synthesis of selective ligands for the CB2 receptor". Bioorganic & Medicinal Chemistry. 7 (12): 2905–14. doi:10.1016/s0968-0896(99)00219-9. PMID 10658595.
  8. Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, Martin BR, Bramblett RD, Reggio PH (September 1996). "Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor". Journal of Medicinal Chemistry. 39 (20): 3875–7. doi:10.1021/JM960394Y. PMID 8831752.
  9. Bow EW, Rimoldi JM. The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation. Perspect Medicin Chem. 2016 Jun 28;8:17-39. doi:10.4137/PMC.S32171 PMID 27398024
  10. ^ Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR (February 2003). "3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor". Bioorganic & Medicinal Chemistry. 11 (4): 539–49. doi:10.1016/S0968-0896(02)00451-0. PMID 12538019. S2CID 29107765.
  11. Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK. Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists. J Pharmacol Exp Ther. 1999 Sep;290(3):1065-79. PMID 10454479
  12. ^ Howlett AC, Barth F, Bonner TI, Cabral G, Casellas P, Devane WA, Felder CC, Herkenham M, Mackie K, Martin BR, Mechoulam R, Pertwee RG (June 2002). "International Union of Pharmacology. XXVII. Classification of cannabinoid receptors". Pharmacological Reviews. 54 (2): 161–202. doi:10.1124/pr.54.2.161. PMID 12037135. S2CID 8259002.
  13. ^ Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR (October 2006). "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors". Bioorganic & Medicinal Chemistry Letters. 16 (20): 5432–5. doi:10.1016/j.bmcl.2006.07.051. PMID 16889960.
  14. ^ Marriott KS, Huffman JW (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.
  15. ^ Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (September 2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223.
  16. Huffman JW, Bushell SM, Miller JR, Wiley JL, Martin BR (December 2002). "1-Methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: new selective ligands for the CB2 receptor". Bioorganic & Medicinal Chemistry. 10 (12): 4119–29. doi:10.1016/s0968-0896(02)00331-0. PMID 12413866.
  17. ^ Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW (2012). "Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents". Bioorganic & Medicinal Chemistry. 20 (6): 2067–2081. doi:10.1016/j.bmc.2012.01.038. PMC 3298571. PMID 22341572.
  18. The Cannabinoid Receptors. The Receptors. 2009. doi:10.1007/978-1-59745-503-9. ISBN 978-1-58829-712-9.
Cannabinoids
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