List of JWH cannabinoids

From Wikipedia the free encyclopedia

The John W. Huffman research group at Clemson University synthesized over 450 cannabinoids.[1][2][3][4] Some of those are:

Cannabinoids and their Ki values[a]
Name Class Ki / nM at CB1 Ki / nM at CB2 Selectivity Structure
JWH-004 Naphthoylindole 48 ± 13 4 ± 1.5 CB2 (12x)
JWH-007[5] 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[5] Naphthoylindole 164 ± 22 13.8 ± 4.6 CB2 (12x)
JWH-016 Naphthoylindole 22 ± 1.5 4.3 ± 1.6 CB2 (5.1x)
JWH-018[5] 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[6] Naphthoylindole >10000 5050 ± 192 CB2
JWH-043[6] Naphthoylindole 1180 ± 44 964 ± 242 CB2 (1.2x)
JWH-044 Naphthoylpyrrole >10000 >10000 —
JWH-045 Naphthoylpyrrole >10000 >10000 —
JWH-046[6] Naphthoylindole 343 ± 38 16.3 ± 4.9 CB2 (21x)
JWH-047[6] Naphthoylindole 59 ± 3 3.47 ± 1.80 CB2 (17x)
JWH-048[6] Naphthoylindole 10.7 ± 1.0 0.49 ± 0.13 CB2 (22x)
JWH-049[6] Naphthoylindole 55.1 ± 17.0 32.3 ± 2.4 CB2 (1.7x)
JWH-050[6] Naphthoylindole 342 ± 6 526 ± 133 CB1 (1.5x)
JWH-051 Dibenzopyran 1.20 0.03 CB2 (40x)
JWH-056[7] Dibenzopyran >10000 32 ± 9 CB2
JWH-057[8] Dibenzopyran 23 ± 7 2.9 ± 1.6 CB2 (8x)
JWH-065[7] Dibenzopyran 399 ± 76 10 ± 2 CB2 (40x)
JWH-070[6] Naphthoylindole >10000 >10000
JWH-071[6] 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[5] Naphthoylindole 214 ± 11 106 ± 46 CB2 (2x)
JWH-077[6] Naphthoylindole >10000 >10000
JWH-078[6] Naphthoylindole 817 ± 60 633 ± 116 CB2 (1.3x)
JWH-079[6] Naphthoylindole 63.0 ± 3.0 32.0 ± 6.0 CB2 (2x)
JWH-080[6] Naphthoylindole 8.9 ± 1.8 2.21 ± 1.30 CB2 (4x)
JWH-081[6] Naphthoylindole 1.2 ± 0.03 12.4 ± 2.2 CB1 (10x)
JWH-082[6] Naphthoylindole 5.3 ± 0.8 6.40 ± 0.94 CB1 (1.2x)
JWH-083[6] Naphthoylindole 106 ± 12 102 ± 50 —
JWH-091[9] (Δ8-THCP) Dibenzopyran 22.0 ± 3.9
JWH-093[6] Naphthoylindole 40.7 ± 2.8 59.1 ± 10.5 CB1 (1.45x)
JWH-094[6] Naphthoylindole 476 ± 67 97.3 ± 2.7 CB2 (4.9x)
JWH-095[6] Naphthoylindole 140 ± 4.3 312 ± 83 CB1 (2.2x)
JWH-096[6] Naphthoylindole 33.7 ± 2.9 13.3 ± 5.6 CB2 (2.5x)
JWH-097[6] Naphthoylindole 455 ± 28 121 ± 15 CB2 (3.8x)
JWH-098[6] Naphthoylindole 4.5 ± 0.1 1.9 ± 0.3 CB2 (2.4x)
JWH-099[6] Naphthoylindole 35.3 ± 9.0 17.8 ± 2.9 CB2 (2x)
JWH-100[6] Naphthoylindole 381 ± 102 155 ± 74 CB2 (2.5x)
JWH-102[7] Dibenzopyran 7.9 ± 0.9 5.2 ± 2.0 CB2 (1.5x)
JWH-103[7] Dibenzopyran 28 ± 3 23 ± 7 CB2 (1.2x)
JWH-116[10] Naphthoylindole 52 ± 5
JWH-120[5] Naphthoylindole 1054 ± 31 6.1 ± 0.7 CB2 (173x)
JWH-122[10] Naphthoylindole 0.69 ± 0.05 1.2 ± 1.2 —
JWH-124 (Δ8-Parahexyl) Dibenzopyran 41.0 ± 3.8
JWH-130 (Δ8-THCB) Dibenzopyran 65.0 ± 13
JWH-133[7] Dibenzopyran 677 ± 132 3.4 ± 1.0 CB2 (200x)
JWH-138[11] Dibenzopyran 8.5 ± 1.4
JWH-139[12] Dibenzopyran 2290 ± 505 14 ± 10 CB2 (164x)
JWH-142[7] Dibenzopyran 529 ± 49 35 ± 14 CB2 (15x)
JWH-143[7] Dibenzopyran 924 ± 104 65 ± 8 CB2 (14x)
JWH-145[13] Naphthoylpyrrole 14 ± 2 6.4 ± 0.4 CB2 (2.2x)
JWH-146[13] Naphthoylpyrrole 21 ± 2 62 ± 5 CB2 (3.0x)
JWH-147[13] Naphthoylpyrrole 11 ± 1 7.1 ± 0.2 CB2 (1.5x)
JWH-148[5] Naphthoylindole 123 ± 8 14.0 ± 1.0 CB2 (8x)
JWH-149[5] Naphthoylindole 5.0 ± 2.1 0.73 ± 0.03 CB2 (6.8x)
JWH-150[13] Naphthoylpyrrole 60 ± 1 15 ± 2 CB2 (4x)
JWH-151[5] Naphthoylindole >10000 30 ± 1.1 CB2 (>333x)
JWH-153[5] Naphthoylindole 250 ± 24 11 ± 0.5 CB2 (23x)
JWH-156[13] Naphthoylpyrrole 404 ± 18 104 ± 18 CB2 (4x)
JWH-159[5] Naphthoylindole 45 ± 1 10.4 ± 1.4 CB2 (4.3x)
JWH-160[5] Naphthoylindole 1568 ± 201 441 ± 110 CB2 (3.6x)
JWH-161 Dibenzopyran hybrid 19.0
JWH-163[5] Naphthoylindole 2358 ± 215 138 ± 12 CB2 (17x)
JWH-164[5] Naphthoylindole 6.6 ± 0.7 6.9 ± 0.2 —
JWH-165[5] Naphthoylindole 204 ± 26 71 ± 8 CB2 (2.9x)
JWH-166[5] 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[10] Naphthylmethylindole 22 ± 2
JWH-176[10] Hydrocarbon 26 ± 4
JWH-180[5] Naphthoylindole 26 ± 2 9.6 ± 2.0 CB2 (2.7x)
JWH-181[5] Naphthoylindole 1.3 ± 0.1 0.62 ± 0.04 CB2 (2.1x)
JWH-182[5] Naphthoylindole 0.65 ± 0.03 1.1 ± 0.1 CB1 (1.7x)
JWH-184[10] Naphthylmethylindole 23 ± 6
JWH-185[10] Naphthylmethylindole 17 ± 3
JWH-186[14] Dibenzopyran 187 ± 23 5.6 ± 1.7 CB2 (33x)
JWH-187[14] Dibenzopyran 84 ± 16 3.4 ± 0.5 CB2 (25x)
JWH-188[14] Dibenzopyran 270 ± 58 18 ± 2 CB2 (15x)
JWH-189[5] Naphthoylindole 52 ± 2 12 ± 0.8 CB2 (4.3x)
JWH-190[14] Dibenzopyran 8.8 ± 1.4 1.6 ± 0.03 CB2 (5.5x)
JWH-191[14] Dibenzopyran 1.8 ± 0.3 0.52 ± 0.03 CB2 (3.5x)
JWH-192[10] Naphthylmethylindole 41 ± 13
JWH-193[10] Naphthoylindole 6 ± 1
JWH-194[10] Naphthylmethylindole 127 ± 19
JWH-195[10] Naphthylmethylindole 113 ± 28
JWH-196[10] Naphthylmethylindole 151 ± 18
JWH-197[10] Naphthylmethylindole 323 ± 98
JWH-198[10] Naphthoylindole 10 ± 2
JWH-199[10] Naphthylmethylindole 20 ± 2
JWH-200[10] Naphthoylindole 42 ± 5
JWH-201[15] Phenylacetylindole 1064 ± 21 444 ± 14 CB2 (2.4x)
JWH-202[15] Phenylacetylindole 1678 ± 63 645 ± 6 CB2 (2.6x)
JWH-203[15] Phenylacetylindole 8.0 ± 0.9 7.0 ± 1.3 —
JWH-204[15] Phenylacetylindole 13 ± 1 25 ± 1 CB1 (1.9x)
JWH-205[15] Phenylacetylindole 124 ± 23 180 ± 9 CB1 (1.45x)
JWH-206[15] Phenylacetylindole 389 ± 25 498 ± 37 CB1 (1.28x)
JWH-207[15] Phenylacetylindole 1598 ± 134 3723 ± 10 CB1 (2.33x)
JWH-208[15] Phenylacetylindole 179 ± 7 570 ± 127 CB1 (3.18x)
JWH-209[15] Phenylacetylindole 746 ± 49 1353 ± 270 CB1 (1.81x)
JWH-210[5] Naphthoylindole 0.46 ± 0.03 0.69 ± 0.01 CB1 (1.5x)
JWH-211[5] Naphthoylindole 70 ± 0.8 12 ± 0.8 CB2 (5.8x)
JWH-212[5] Naphthoylindole 33 ± 0.9 10 ± 1.2 CB2 (3.3x)
JWH-213[5] Naphthoylindole 1.5 ± 0.2 0.42 ± 0.05 CB2 (3.6x)
JWH-215[14] Dibenzopyran 1008 ± 117 85 ± 21 CB2 (12x)
JWH-216[14] Dibenzopyran 1856 ± 148 333 ± 104 CB2 (5.6x)
JWH-217[14] Dibenzopyran >10000 1404 ± 66 CB2 (>7x)
JWH-220 Hydrocarbon 19
JWH-224[14] Dibenzopyran 347 ± 34 28 ± 1 CB2 (12.3x)
JWH-225[14] Dibenzopyran >10000 325 ± 70 CB2 (>31x)
JWH-226[14] Dibenzopyran 4001 ± 282 43 ± 3 CB2 (93x)
JWH-227[14] Dibenzopyran 40 ± 6 4.4 ± 0.3 CB2 (9x)
JWH-229[16] Dibenzopyran 3134 ± 110 18 ± 2 CB2 (174x)
JWH-230[14] Dibenzopyran 15 ± 3 1.4 ± 0.12 CB2 (10.7x)
JWH-233[14] Dibenzopyran 14 ± 3 1.0 ± 0.3 CB2 (14x)
JWH-234[5] Naphthoylindole 8.4 ± 1.8 3.8 ± 0.6 CB2 (2.2x)
JWH-235[5] Naphthoylindole 338 ± 34 123 ± 34 CB2 (2.7x)
JWH-236[5] Naphthoylindole 1351 ± 204 240 ± 63 CB2 (5.6x)
JWH-237[15] Phenylacetylindole 38 ± 10 106 ± 2 CB1 (2.8x)
JWH-239[5] Naphthoylindole 342 ± 20 52 ± 6 CB2 (6.6x)
JWH-240[5] Naphthoylindole 14 ± 1 7.2 ± 1.3 CB2 (1.9x)
JWH-241[5] Naphthoylindole 147 ± 20 49 ± 7 CB2 (3.0x)
JWH-242[5] Naphthoylindole 42 ± 9 6.5 ± 0.3 CB2 (6.5x)
JWH-243[13] Naphthoylpyrrole 285 ± 40 41 ± 3 CB2 (6.95x)
JWH-244[13] Naphthoylpyrrole 130 ± 6 18 ± 1 CB2 (7.22x)
JWH-245[13] Naphthoylpyrrole 276 ± 4 25 ± 2 CB2 (11x)
JWH-246[13] Naphthoylpyrrole 70 ± 4 16 ± 1 CB2 (4.38x)
JWH-247[14] Dibenzopyran 427 ± 31 99 ± 4 CB2 (4.3x)
JWH-248[15] Phenylacetylindole 1028 ± 39 657 ± 19 CB2 (1.56x)
JWH-249[15] Phenylacetylindole 8.4 ± 1.8 20 ± 2 CB1 (2.38x)
JWH-250[15] Phenylacetylindole 11 ± 2 33 ± 2 CB1 (3x)
JWH-251[15] Phenylacetylindole 29 ± 3 146 ± 36 CB2 (5x)
JWH-252[15] Phenylacetylindole 23 ± 3 19 ± 1 CB2 (1.2x)
JWH-253[15] Phenylacetylindole 62 ± 10 84 ± 12 CB1 (1.35x)
JWH-254[14] Dibenzopyran 4724 ± 509 319 ± 16 CB2 (14.8x)
JWH-256[14] Dibenzopyran 4300 ± 888 97 ± 18 CB2 (44x)
JWH-258[5] Naphthoylindole 4.6 ± 0.6 10.5 ± 1.3 CB1 (2.3x)
JWH-259[5] Naphthoylindole 220 ± 29 74 ± 7 CB2 (3.0x)
JWH-260[5] Naphthoylindole 29 ± 0.4 25 ± 1.9 CB2 (1.2x)
JWH-261[5] Naphthoylindole 767 ± 105 221 ± 14 CB2 (3.5x)
JWH-262[5] Naphthoylindole 28 ± 3 5.6 ± 0.7 CB2 (5.0x)
JWH-265[5] Naphthoylindole 3788 ± 323 80 ± 13 CB2 (47x)
JWH-266[5] Naphthoylindole >10000 455 ± 55 CB2 (>22x)
JWH-267[5] Naphthoylindole 381 ± 16 7.2 ± 0.14 CB2 (53x)
JWH-268[5] Naphthoylindole 1379 ± 193 40 ± 0.6 CB2 (34x)
JWH-277[14] Dibenzopyran 3905 ± 91 589 ± 65 CB2 (6.6x)
JWH-278[14] Dibenzopyran 906 ± 80 69 ± 6 CB2 (13x)
JWH-292[13] Naphthoylpyrrole 29 ± 1 20 ± 1 CB2 (1.45x)
JWH-293[13] Naphthoylpyrrole 100 ± 5 41 ± 4 CB2 (2.44x)
JWH-298[14] Dibenzopyran 812 ± 67 198 ± 23 CB2 (4.1x)
JWH-299[14] Dibenzopyran 415 ± 50 30 ± 2 CB2 (13.8x)
JWH-300[12] Dibenzopyran 118 ± 16 5.3 ± 0.1 CB2 (22x)
JWH-301[14] Dibenzopyran 295 ± 64 48 ± 4 CB2 (6.1x)
JWH-302[15] Phenylacetylindole 17 ± 2 89 ± 15 CB1 (5.26x)
JWH-303[15] Phenylacetylindole 117 ± 10 138 ± 12 CB1 (1.18x)
JWH-304[15] Phenylacetylindole 3363 ± 332 2679 ± 688 CB2 (1.26x)
JWH-305[15] Phenylacetylindole 15 ± 1.8 29 ± 5 CB1 (1.93x)
JWH-306[15] Phenylacetylindole 25 ± 1 82 ± 11 CB1 (3.28x)
JWH-307[13] Naphthoylpyrrole 7.7 ± 1.8 3.3 ± 0.2 CB2 (2.33x)
JWH-308[13] Naphthoylpyrrole 41 ± 1 33 ± 2 CB2 (1.24x)
JWH-309[13] Naphthoylpyrrole 41 ± 3 49 ± 7 CB1 (1.20x)
JWH-310[14] Dibenzopyran 1059 ± 51 36 ± 3 CB2 (29x)
JWH-311[15] Phenylacetylindole 23 ± 2 39 ± 3 CB1 (1.70x)
JWH-312[15] Phenylacetylindole 72 ± 7 91 ± 20 CB1 (1.26x)
JWH-313[15] Phenylacetylindole 422 ± 19 365 ± 92 CB2 (1.16x)
JWH-314[15] Phenylacetylindole 39 ± 2 76 ± 4 CB1 (1.95x)
JWH-315[15] Phenylacetylindole 430 ± 24 182 ± 23 CB2 (3.36x)
JWH-316[15] Phenylacetylindole 2862 ± 670 781 ± 105 CB2 (3.66x)
JWH-336[12] Dibenzopyran 4589 ± 367 153 ± 15 CB2 (30x)
JWH-338[14] Dibenzopyran >10000 111 ± 16 CB2 (>90x)
JWH-339[14] Dibenzopyran >10000 2317 ± 93 CB2 (>4.3x)
JWH-340[14] Dibenzopyran 135 ± 6 30 ± 1 CB2 (4.5x)
JWH-341[14] Dibenzopyran 100 ± 8 10 ± 0.1 CB2 (10x)
JWH-346[13] Naphthoylpyrrole 67 ± 6 39 ± 2 CB2 (1.72x)
JWH-347[13] Naphthoylpyrrole 333 ± 17 169 ± 17 CB2 (1.97x)
JWH-348[13] Naphthoylpyrrole 218 ± 19 53 ± 1 CB2 (4.11x)
JWH-349[14] Dibenzopyran 376 ± 1 38 ± 4 CB2 (9.9x)
JWH-350[12] Dibenzopyran 395 ± 50 12 ± 1 CB2 (33x)
JWH-351[14] Dibenzopyran >10000 295 ± 3 CB2 (>34x)
JWH-352[14] Dibenzopyran >10000 47 ± 2 CB2 (>213x)
JWH-353[14] Dibenzopyran 1493 ± 10 31 ± 1 CB2 (48x)
JWH-354[14] Dibenzopyran 1961 ± 21 241 ± 14 CB2 (8.1x)
JWH-355[14] Dibenzopyran 2162 ± 220 108 ± 17 CB2 (20x)
JWH-356[14] Dibenzopyran 5837 ± 701 108 ± 17 CB2 (54x)
JWH-357[14] Dibenzopyran 647 ± 78 185 ± 4 CB2 (3.5x)
JWH-358[14] Dibenzopyran 1243 ± 266 52 ± 3 CB2 (24x)
JWH-359 Dibenzopyran 2918 ± 450 13.0 ± 0.2 CB2 (220x)
JWH-360[14] Dibenzopyran 2449 ± 606 160 ± 8 CB2 (15x)
JWH-361[14] Dibenzopyran 63 ± 3 2.7 ± 0.1 CB2 (23x)
JWH-362[14] Dibenzopyran 127 ± 8 34 ± 5 CB2 (3.7x)
JWH-363[13] Naphthoylpyrrole 245 ± 5 71 ± 1 CB2 (3.45x)
JWH-364[13] Naphthoylpyrrole 34 ± 3 29 ± 1 CB2 (1.17x)
JWH-365[13] Naphthoylpyrrole 17 ± 1 3.4 ± 0.2 CB2 (5.0x)
JWH-366[13] Naphthoylpyrrole 191 ± 12 24 ± 1 CB2 (7.96x)
JWH-367[13] Naphthoylpyrrole 53 ± 2 23 ± 1 CB2 (2.30x)
JWH-368[13] Naphthoylpyrrole 16 ± 1 9.1 ± 0.7 CB2 (1.76x)
JWH-369[13] Naphthoylpyrrole 7.9 ± 0.4 5.2 ± 0.3 CB2 (1.52x)
JWH-370[13] Naphthoylpyrrole 5.6 ± 0.4 4.0 ± 0.5 CB2 (1.40x)
JWH-371[13] Naphthoylpyrrole 42 ± 1 64 ± 2 CB1 (1.52x)
JWH-372[13] Naphthoylpyrrole 77 ± 2 8.2 ± 0.2 CB1 (9.39x)
JWH-373[13] Naphthoylpyrrole 60 ± 3 69 ± 2 CB1 (1.15x)
JWH-387[17] Naphthoylindole 1.2 ± 0.1 1.1 ± 0.1 —
JWH-398[18] Naphthoylindole 2.3 ± 0.1 2.8 ± 0.2 CB1 (1.22x)
JWH-416[17] Naphthoylindole 73 ± 10 3.3 ± 0.1 CB2 (22x)
JWH-417[17] Naphthoylindole 522 ± 58 13 ± 0.2 CB2 (40x)
JWH-422[17] Naphthoylindole 501 ± 48 20 ± 0.4 CB2 (25x)
JWH-423[17] Naphthoylindole 140 ± 10 6.6 ± 0.2 CB2 (21x)
JWH-424[17] Naphthoylindole 21 ± 3.4 5.4 ± 0.2 CB2 (3.9x)
JWH-425[17] Naphthoylindole 54 ± 11 10 ± 0.4 CB2 (5.4x)


See also

[edit]

Notes

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

References

[edit]
  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. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah ai aj ak al am 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. ^ a b c d e f g h i j k l m n o p q r s t u v w x 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. ^ a b c d e f g 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. ^ a b c d e f g h i j k l m n o 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. ^ a b c d 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. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab 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. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah ai aj ak al am 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. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa 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. ^ a b c d e f g 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.
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