List of JWH cannabinoids

Last updated

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

Contents

Cannabinoids and their Ki values [a]
NameClassKi / nM at CB1Ki / nM at CB2SelectivityStructure
JWH-004 Naphthoylindole 48 ± 134 ± 1.5CB2 (12x) JWH-004.svg
JWH-007 [5] Naphthoylindole 9.5 ± 4.52.9 ± 2.6CB2 (3.3x) JWH-007.svg
JWH-009 Naphthoylindole >10000141 ± 14CB2 (>70x) JWH-009.svg
JWH-011 Naphthoylindole JWH-011.svg
JWH-015 [5] Naphthoylindole164 ± 2213.8 ± 4.6CB2 (12x) JWH 015.svg
JWH-016 Naphthoylindole22 ± 1.54.3 ± 1.6CB2 (5.1x) JWH-016.svg
JWH-018 [5] Naphthoylindole9 ± 52.9 ± 2.6CB2 (3.1x) JWH 018.svg
JWH-019 Naphthoylindole9.8 ± 25.55 ± 2CB2 (1.77x) JWH 019.svg
JWH-020 Naphthoylindole128 ± 17205 ± 20CB1 (1.6x) JWH-020.svg
JWH-030 Naphthoylpyrrole 87 ± 3320 ± 127CB1 (3.7x) JWH 030.svg
JWH-031 Naphthoylpyrrole399 ± 109 JWH-031.svg
JWH-032 Naphthoylpyrrole>10000>10000— JWH-032.svg
JWH-033 Naphthoylpyrrole666 ± 77 JWH-033.svg
JWH-036 Naphthoylpyrrole309 ± 11 JWH-036.svg
JWH-042 [6] Naphthoylindole>100005050 ± 192CB2 JWH-042.svg
JWH-043 [6] Naphthoylindole1180 ± 44964 ± 242CB2 (1.2x) JWH-043.svg
JWH-044 Naphthoylpyrrole>10000>10000— JWH-044.svg
JWH-045 Naphthoylpyrrole>10000>10000— JWH-045.svg
JWH-046 [6] Naphthoylindole343 ± 3816.3 ± 4.9CB2 (21x) JWH-046.svg
JWH-047 [6] Naphthoylindole59 ± 33.47 ± 1.80CB2 (17x) JWH-047.svg
JWH-048 [6] Naphthoylindole10.7 ± 1.00.49 ± 0.13CB2 (22x) JWH-048.png
JWH-049 [6] Naphthoylindole55.1 ± 17.032.3 ± 2.4CB2 (1.7x) JWH-049.svg
JWH-050 [6] Naphthoylindole342 ± 6526 ± 133CB1 (1.5x) JWH-050.svg
JWH-051 Dibenzopyran 1.200.03CB2 (40x) JWH-051.svg
JWH-056 [7] Dibenzopyran>1000032 ± 9CB2 JWH-056.svg
JWH-057 [8] Dibenzopyran23 ± 72.9 ± 1.6CB2 (8x) JWH-057.svg
JWH-065 [7] Dibenzopyran399 ± 7610 ± 2CB2 (40x) JWH-065.svg
JWH-070 [6] Naphthoylindole>10000>10000 JWH-070.svg
JWH-071 [6] Naphthoylindole1340 ± 1232940 ± 852CB1 (2.2x) JWH-071.svg
JWH-072 Naphthoylindole1050 ± 5.5170 ± 54CB2 (6x) JWH-072.svg
JWH-073 Naphthoylindole8.9 ± 1.827 ± 12CB1 (3x) JWH 073.svg
JWH-076 [5] Naphthoylindole214 ± 11106 ± 46CB2 (2x) JWH-076.svg
JWH-077 [6] Naphthoylindole>10000>10000 JWH-077.svg
JWH-078 [6] Naphthoylindole817 ± 60633 ± 116CB2 (1.3x) JWH-078.svg
JWH-079 [6] Naphthoylindole63.0 ± 3.032.0 ± 6.0CB2 (2x) JWH-079.svg
JWH-080 [6] Naphthoylindole8.9 ± 1.82.21 ± 1.30CB2 (4x) JWH-080.svg
JWH-081 [6] Naphthoylindole1.2 ± 0.0312.4 ± 2.2CB1 (10x) JWH 081.svg
JWH-082 [6] Naphthoylindole5.3 ± 0.86.40 ± 0.94CB1 (1.2x) JWH-082.svg
JWH-083 [6] Naphthoylindole106 ± 12102 ± 50— JWH-083.svg
JWH-091 [9] (Δ8-THCP)Dibenzopyran22.0 ± 3.9 JWH-091 structure.png
JWH-093 [6] Naphthoylindole40.7 ± 2.859.1 ± 10.5CB1 (1.45x) JWH-093.svg
JWH-094 [6] Naphthoylindole476 ± 6797.3 ± 2.7CB2 (4.9x) JWH-094.svg
JWH-095 [6] Naphthoylindole140 ± 4.3312 ± 83CB1 (2.2x) JWH-095.svg
JWH-096 [6] Naphthoylindole33.7 ± 2.913.3 ± 5.6CB2 (2.5x) JWH-096.svg
JWH-097 [6] Naphthoylindole455 ± 28121 ± 15CB2 (3.8x) JWH-097.svg
JWH-098 [6] Naphthoylindole4.5 ± 0.11.9 ± 0.3CB2 (2.4x) JWH-098.svg
JWH-099 [6] Naphthoylindole35.3 ± 9.017.8 ± 2.9CB2 (2x) JWH-099.svg
JWH-100 [6] Naphthoylindole381 ± 102155 ± 74CB2 (2.5x) JWH-100.svg
JWH-102 [7] Dibenzopyran7.9 ± 0.95.2 ± 2.0CB2 (1.5x) JWH-102.svg
JWH-103 [7] Dibenzopyran28 ± 323 ± 7CB2 (1.2x) JWH-103.svg
JWH-116 [10] Naphthoylindole52 ± 5 JWH-116.svg
JWH-120 [5] Naphthoylindole1054 ± 316.1 ± 0.7CB2 (173x) JWH-120.png
JWH-122 [10] Naphthoylindole0.69 ± 0.051.2 ± 1.2— JWH-122.svg
JWH-124 (Δ8-Parahexyl)Dibenzopyran41.0 ± 3.8 JWH-124 structure.png
JWH-130 (Δ8-THCB)Dibenzopyran65.0 ± 13 JWH-130 structure.png
JWH-133 [7] Dibenzopyran677 ± 1323.4 ± 1.0CB2 (200x) JWH-133.png
JWH-138 [11] Dibenzopyran8.5 ± 1.4 JWH-138 structure.png
JWH-139 [12] Dibenzopyran2290 ± 50514 ± 10CB2 (164x) JWH-139.svg
JWH-142 [7] Dibenzopyran529 ± 4935 ± 14CB2 (15x) JWH-142.svg
JWH-143 [7] Dibenzopyran924 ± 10465 ± 8CB2 (14x) JWH-143.svg
JWH-145 [13] Naphthoylpyrrole14 ± 26.4 ± 0.4CB2 (2.2x) JWH-145.svg
JWH-146 [13] Naphthoylpyrrole21 ± 262 ± 5CB2 (3.0x) JWH-146.svg
JWH-147 [13] Naphthoylpyrrole11 ± 17.1 ± 0.2CB2 (1.5x) JWH 147.svg
JWH-148 [5] Naphthoylindole123 ± 814.0 ± 1.0CB2 (8x) JWH-148.png
JWH-149 [5] Naphthoylindole5.0 ± 2.10.73 ± 0.03CB2 (6.8x) JWH-149.png
JWH-150 [13] Naphthoylpyrrole60 ± 115 ± 2CB2 (4x) JWH-150.svg
JWH-151 [5] Naphthoylindole>1000030 ± 1.1CB2 (>333x) JWH-151.svg
JWH-153 [5] Naphthoylindole250 ± 2411 ± 0.5CB2 (23x) JWH-153.svg
JWH-156 [13] Naphthoylpyrrole404 ± 18104 ± 18CB2 (4x) JWH-156.svg
JWH-159 [5] Naphthoylindole45 ± 110.4 ± 1.4CB2 (4.3x) JWH-159.svg
JWH-160 [5] Naphthoylindole1568 ± 201441 ± 110CB2 (3.6x) JWH-160.svg
JWH-161 Dibenzopyran hybrid19.0 JWH-161.svg
JWH-163 [5] Naphthoylindole2358 ± 215138 ± 12CB2 (17x) JWH-163.svg
JWH-164 [5] Naphthoylindole6.6 ± 0.76.9 ± 0.2— JWH-164.svg
JWH-165 [5] Naphthoylindole204 ± 2671 ± 8CB2 (2.9x) JWH-165.svg
JWH-166 [5] Naphthoylindole44 ± 101.9 ± 0.08CB2 (23x) JWH-166.svg
JWH-167 Phenylacetylindole 90 ± 17159 ± 14CB1 (1.77x) JWH-167.svg
JWH-171 Hydrocarbon 51 JWH-171.svg
JWH-175 [10] Naphthylmethylindole 22 ± 2 JWH-175.svg
JWH-176 [10] Hydrocarbon26 ± 4 JWH 176.svg
JWH-180 [5] Naphthoylindole26 ± 29.6 ± 2.0CB2 (2.7x) JWH-180.svg
JWH-181 [5] Naphthoylindole1.3 ± 0.10.62 ± 0.04CB2 (2.1x) JWH-181.svg
JWH-182 [5] Naphthoylindole0.65 ± 0.031.1 ± 0.1CB1 (1.7x) JWH-182.svg
JWH-184 [10] Naphthylmethylindole23 ± 6 JWH-184.svg
JWH-185 [10] Naphthylmethylindole17 ± 3 JWH-185.svg
JWH-186 [14] Dibenzopyran187 ± 235.6 ± 1.7CB2 (33x) JWH-186.svg
JWH-187 [14] Dibenzopyran84 ± 163.4 ± 0.5CB2 (25x) JWH-187.svg
JWH-188 [14] Dibenzopyran270 ± 5818 ± 2CB2 (15x) JWH-188.svg
JWH-189 [5] Naphthoylindole52 ± 212 ± 0.8CB2 (4.3x) JWH-189.svg
JWH-190 [14] Dibenzopyran8.8 ± 1.41.6 ± 0.03CB2 (5.5x) JWH-190.svg
JWH-191 [14] Dibenzopyran1.8 ± 0.30.52 ± 0.03CB2 (3.5x) JWH-191.svg
JWH-192 [10] Naphthylmethylindole41 ± 13 JWH-192.svg
JWH-193 [10] Naphthoylindole6 ± 1 JWH-193.svg
JWH-194 [10] Naphthylmethylindole127 ± 19 JWH-194.svg
JWH-195 [10] Naphthylmethylindole113 ± 28 JWH-195.svg
JWH-196 [10] Naphthylmethylindole151 ± 18 JWH-196.svg
JWH-197 [10] Naphthylmethylindole323 ± 98 JWH-197.svg
JWH-198 [10] Naphthoylindole10 ± 2 JWH-198.svg
JWH-199 [10] Naphthylmethylindole20 ± 2 JWH-199.svg
JWH-200 [10] Naphthoylindole42 ± 5 JWH-200.svg
JWH-201 [15] Phenylacetylindole1064 ± 21444 ± 14CB2 (2.4x) JWH-201.svg
JWH-202 [15] Phenylacetylindole1678 ± 63645 ± 6CB2 (2.6x) JWH-202.svg
JWH-203 [15] Phenylacetylindole8.0 ± 0.97.0 ± 1.3— JWH-203.svg
JWH-204 [15] Phenylacetylindole13 ± 125 ± 1CB1 (1.9x) JWH-204.svg
JWH-205 [15] Phenylacetylindole124 ± 23180 ± 9CB1 (1.45x) JWH-205.svg
JWH-206 [15] Phenylacetylindole389 ± 25498 ± 37CB1 (1.28x) JWH-206.svg
JWH-207 [15] Phenylacetylindole1598 ± 1343723 ± 10CB1 (2.33x) JWH-207.svg
JWH-208 [15] Phenylacetylindole179 ± 7570 ± 127CB1 (3.18x) JWH-208.svg
JWH-209 [15] Phenylacetylindole746 ± 491353 ± 270CB1 (1.81x) JWH-209.svg
JWH-210 [5] Naphthoylindole0.46 ± 0.030.69 ± 0.01CB1 (1.5x) JWH-210.svg
JWH-211 [5] Naphthoylindole70 ± 0.812 ± 0.8CB2 (5.8x) JWH-211.svg
JWH-212 [5] Naphthoylindole33 ± 0.910 ± 1.2CB2 (3.3x) JWH-212.svg
JWH-213 [5] Naphthoylindole1.5 ± 0.20.42 ± 0.05CB2 (3.6x) JWH-213.svg
JWH-215 [14] Dibenzopyran1008 ± 11785 ± 21CB2 (12x) JWH-215.svg
JWH-216 [14] Dibenzopyran1856 ± 148333 ± 104CB2 (5.6x) JWH-216.svg
JWH-217 [14] Dibenzopyran>100001404 ± 66CB2 (>7x) JWH-217.svg
JWH-220 Hydrocarbon19 JWH-220.svg
JWH-224 [14] Dibenzopyran347 ± 3428 ± 1CB2 (12.3x) JWH-224.svg
JWH-225 [14] Dibenzopyran>10000325 ± 70CB2 (>31x) JWH-225.svg
JWH-226 [14] Dibenzopyran4001 ± 28243 ± 3CB2 (93x) JWH-226.svg
JWH-227 [14] Dibenzopyran40 ± 64.4 ± 0.3CB2 (9x) JWH-227.svg
JWH-229 [16] Dibenzopyran3134 ± 11018 ± 2CB2 (174x) JWH-229.svg
JWH-230 [14] Dibenzopyran15 ± 31.4 ± 0.12CB2 (10.7x) JWH-230.svg
JWH-233 [14] Dibenzopyran14 ± 31.0 ± 0.3CB2 (14x) JWH-233.svg
JWH-234 [5] Naphthoylindole8.4 ± 1.83.8 ± 0.6CB2 (2.2x) JWH-234.svg
JWH-235 [5] Naphthoylindole338 ± 34123 ± 34CB2 (2.7x) JWH-235.svg
JWH-236 [5] Naphthoylindole1351 ± 204240 ± 63CB2 (5.6x) JWH-236.svg
JWH-237 [15] Phenylacetylindole38 ± 10106 ± 2CB1 (2.8x) JWH-237.svg
JWH-239 [5] Naphthoylindole342 ± 2052 ± 6CB2 (6.6x) JWH-239.svg
JWH-240 [5] Naphthoylindole14 ± 17.2 ± 1.3CB2 (1.9x) JWH-240.svg
JWH-241 [5] Naphthoylindole147 ± 2049 ± 7CB2 (3.0x) JWH-241.svg
JWH-242 [5] Naphthoylindole42 ± 96.5 ± 0.3CB2 (6.5x) JWH-242.svg
JWH-243 [13] Naphthoylpyrrole285 ± 4041 ± 3CB2 (6.95x) JWH-243.svg
JWH-244 [13] Naphthoylpyrrole130 ± 618 ± 1CB2 (7.22x) JWH-244.svg
JWH-245 [13] Naphthoylpyrrole276 ± 425 ± 2CB2 (11x) JWH-245.svg
JWH-246 [13] Naphthoylpyrrole70 ± 416 ± 1CB2 (4.38x) JWH-246.svg
JWH-247 [14] Dibenzopyran427 ± 3199 ± 4CB2 (4.3x) JWH-247.svg
JWH-248 [15] Phenylacetylindole1028 ± 39657 ± 19CB2 (1.56x) JWH-248.svg
JWH-249 [15] Phenylacetylindole8.4 ± 1.820 ± 2CB1 (2.38x) JWH-249.svg
JWH-250 [15] Phenylacetylindole11 ± 233 ± 2CB1 (3x) JWH 250.svg
JWH-251 [15] Phenylacetylindole29 ± 3146 ± 36CB2 (5x) JWH-251.svg
JWH-252 [15] Phenylacetylindole23 ± 319 ± 1CB2 (1.2x) JWH-252.svg
JWH-253 [15] Phenylacetylindole62 ± 1084 ± 12CB1 (1.35x) JWH-253.svg
JWH-254 [14] Dibenzopyran4724 ± 509319 ± 16CB2 (14.8x) JWH-254.svg
JWH-256 [14] Dibenzopyran4300 ± 88897 ± 18CB2 (44x) JWH-256.svg
JWH-258 [5] Naphthoylindole4.6 ± 0.610.5 ± 1.3CB1 (2.3x) JWH-258.svg
JWH-259 [5] Naphthoylindole220 ± 2974 ± 7CB2 (3.0x) JWH-259.svg
JWH-260 [5] Naphthoylindole29 ± 0.425 ± 1.9CB2 (1.2x) JWH-260.svg
JWH-261 [5] Naphthoylindole767 ± 105221 ± 14CB2 (3.5x) JWH-261.svg
JWH-262 [5] Naphthoylindole28 ± 35.6 ± 0.7CB2 (5.0x) JWH-262.svg
JWH-265 [5] Naphthoylindole3788 ± 32380 ± 13CB2 (47x) JWH-265.svg
JWH-266 [5] Naphthoylindole>10000455 ± 55CB2 (>22x) JWH-266.svg
JWH-267 [5] Naphthoylindole381 ± 167.2 ± 0.14CB2 (53x) JWH-267.svg
JWH-268 [5] Naphthoylindole1379 ± 19340 ± 0.6CB2 (34x) JWH-268.svg
JWH-277 [14] Dibenzopyran3905 ± 91589 ± 65CB2 (6.6x) JWH-277.svg
JWH-278 [14] Dibenzopyran906 ± 8069 ± 6CB2 (13x) JWH-278.svg
JWH-292 [13] Naphthoylpyrrole29 ± 120 ± 1CB2 (1.45x) JWH-292.svg
JWH-293 [13] Naphthoylpyrrole100 ± 541 ± 4CB2 (2.44x) JWH-293.svg
JWH-298 [14] Dibenzopyran812 ± 67198 ± 23CB2 (4.1x) JWH-298.svg
JWH-299 [14] Dibenzopyran415 ± 5030 ± 2CB2 (13.8x) JWH-299.svg
JWH-300 [12] Dibenzopyran118 ± 165.3 ± 0.1CB2 (22x) JWH-300.svg
JWH-301 [14] Dibenzopyran295 ± 6448 ± 4CB2 (6.1x) JWH-301.svg
JWH-302 [15] Phenylacetylindole17 ± 289 ± 15CB1 (5.26x) JWH-302.svg
JWH-303 [15] Phenylacetylindole117 ± 10138 ± 12CB1 (1.18x) JWH-303.svg
JWH-304 [15] Phenylacetylindole3363 ± 3322679 ± 688CB2 (1.26x) JWH-304.svg
JWH-305 [15] Phenylacetylindole15 ± 1.829 ± 5CB1 (1.93x) JWH-305.svg
JWH-306 [15] Phenylacetylindole25 ± 182 ± 11CB1 (3.28x) JWH-306.svg
JWH-307 [13] Naphthoylpyrrole7.7 ± 1.83.3 ± 0.2CB2 (2.33x) JWH 307.svg
JWH-308 [13] Naphthoylpyrrole41 ± 133 ± 2CB2 (1.24x) JWH-308.svg
JWH-309 [13] Naphthoylpyrrole41 ± 349 ± 7CB1 (1.20x) JWH-309.svg
JWH-310 [14] Dibenzopyran1059 ± 5136 ± 3CB2 (29x) JWH-310.svg
JWH-311 [15] Phenylacetylindole23 ± 239 ± 3CB1 (1.70x) JWH-311.svg
JWH-312 [15] Phenylacetylindole72 ± 791 ± 20CB1 (1.26x) JWH-312.svg
JWH-313 [15] Phenylacetylindole422 ± 19365 ± 92CB2 (1.16x) JWH-313.svg
JWH-314 [15] Phenylacetylindole39 ± 276 ± 4CB1 (1.95x) JWH-314.svg
JWH-315 [15] Phenylacetylindole430 ± 24182 ± 23CB2 (3.36x) JWH-315.svg
JWH-316 [15] Phenylacetylindole2862 ± 670781 ± 105CB2 (3.66x) JWH-316.svg
JWH-336 [12] Dibenzopyran4589 ± 367153 ± 15CB2 (30x) JWH-336.svg
JWH-338 [14] Dibenzopyran>10000111 ± 16CB2 (>90x) JWH-338.svg
JWH-339 [14] Dibenzopyran>100002317 ± 93CB2 (>4.3x) JWH-339.svg
JWH-340 [14] Dibenzopyran135 ± 630 ± 1CB2 (4.5x) JWH-340.svg
JWH-341 [14] Dibenzopyran100 ± 810 ± 0.1CB2 (10x) JWH-341.svg
JWH-346 [13] Naphthoylpyrrole67 ± 639 ± 2CB2 (1.72x) JWH-346.svg
JWH-347 [13] Naphthoylpyrrole333 ± 17169 ± 17CB2 (1.97x) JWH-347.svg
JWH-348 [13] Naphthoylpyrrole218 ± 1953 ± 1CB2 (4.11x) JWH-348.svg
JWH-349 [14] Dibenzopyran376 ± 138 ± 4CB2 (9.9x) JWH-349.svg
JWH-350 [12] Dibenzopyran395 ± 5012 ± 1CB2 (33x) JWH-350.svg
JWH-351 [14] Dibenzopyran>10000295 ± 3CB2 (>34x) JWH-351.svg
JWH-352 [14] Dibenzopyran>1000047 ± 2CB2 (>213x) JWH-352.svg
JWH-353 [14] Dibenzopyran1493 ± 1031 ± 1CB2 (48x) JWH-353.svg
JWH-354 [14] Dibenzopyran1961 ± 21241 ± 14CB2 (8.1x) JWH-354.svg
JWH-355 [14] Dibenzopyran2162 ± 220108 ± 17CB2 (20x) JWH-355.svg
JWH-356 [14] Dibenzopyran5837 ± 701108 ± 17CB2 (54x) JWH-356.svg
JWH-357 [14] Dibenzopyran647 ± 78185 ± 4CB2 (3.5x) JWH-357.svg
JWH-358 [14] Dibenzopyran1243 ± 26652 ± 3CB2 (24x) JWH-358.svg
JWH-359 Dibenzopyran2918 ± 45013.0 ± 0.2 CB2 (220x) JWH-359.svg
JWH-360 [14] Dibenzopyran2449 ± 606160 ± 8CB2 (15x) JWH-360.svg
JWH-361 [14] Dibenzopyran63 ± 32.7 ± 0.1CB2 (23x) JWH-361.svg
JWH-362 [14] Dibenzopyran127 ± 8 34 ± 5CB2 (3.7x) JWH-362.svg
JWH-363 [13] Naphthoylpyrrole245 ± 571 ± 1CB2 (3.45x) JWH-363.svg
JWH-364 [13] Naphthoylpyrrole34 ± 329 ± 1CB2 (1.17x) JWH-364.svg
JWH-365 [13] Naphthoylpyrrole17 ± 13.4 ± 0.2CB2 (5.0x) JWH-365.svg
JWH-366 [13] Naphthoylpyrrole191 ± 1224 ± 1CB2 (7.96x) JWH-366.svg
JWH-367 [13] Naphthoylpyrrole53 ± 223 ± 1CB2 (2.30x) JWH-367.svg
JWH-368 [13] Naphthoylpyrrole16 ± 19.1 ± 0.7CB2 (1.76x) JWH-368.svg
JWH-369 [13] Naphthoylpyrrole7.9 ± 0.45.2 ± 0.3CB2 (1.52x) JWH-369.svg
JWH-370 [13] Naphthoylpyrrole5.6 ± 0.44.0 ± 0.5CB2 (1.40x) JWH-370.svg
JWH-371 [13] Naphthoylpyrrole42 ± 164 ± 2CB1 (1.52x) JWH-371.svg
JWH-372 [13] Naphthoylpyrrole77 ± 28.2 ± 0.2CB1 (9.39x) JWH-372.svg
JWH-373 [13] Naphthoylpyrrole60 ± 369 ± 2CB1 (1.15x) JWH-373.svg
JWH-387 [17] Naphthoylindole1.2 ± 0.11.1 ± 0.1— JWH-387.svg
JWH-398 [18] Naphthoylindole2.3 ± 0.12.8 ± 0.2CB1 (1.22x) JWH-398.svg
JWH-416 [17] Naphthoylindole73 ± 103.3 ± 0.1CB2 (22x) JWH-416.svg
JWH-417 [17] Naphthoylindole522 ± 5813 ± 0.2CB2 (40x) JWH-417.svg
JWH-422 [17] Naphthoylindole501 ± 4820 ± 0.4CB2 (25x) JWH-422.svg
JWH-423 [17] Naphthoylindole140 ± 106.6 ± 0.2CB2 (21x) JWH-423.svg
JWH-424 [17] Naphthoylindole21 ± 3.45.4 ± 0.2CB2 (3.9x) JWH-424.svg
JWH-425 [17] Naphthoylindole54 ± 1110 ± 0.4CB2 (5.4x) JWH-425.svg


See also

Notes

Related Research Articles

<span class="mw-page-title-main">JWH-081</span> Chemical compound

JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype is measured at approximately 10x the affinity at CB2(12.4nM). It was discovered by and named after John W. Huffman.

<span class="mw-page-title-main">JWH-147</span> Chemical compound

JWH-147 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 11.0 nM at CB1 vs 7.1 nM at CB2. It was discovered and named after the renowned professor of organic chemistry John W. Huffman.

<span class="mw-page-title-main">JWH-307</span> Chemical compound

JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 7.7 nM at CB1 vs 3.3 nM at CB2. It was discovered by, and named after, John W. Huffman. JWH-307 was detected as an ingredient in synthetic cannabis smoking blends in 2012, initially in Germany.

<span class="mw-page-title-main">JWH-359</span> Chemical compound

JWH-359 is a dibenzopyran "classical" cannabinoid drug, which is a potent and selective CB2 receptor agonist, with a Ki of 13.0 nM and selectivity of around 220 times for CB2 over CB1 receptors. It is related to other dibenzopyran CB2 agonists such as JWH-133 and L-759,656 but with a chiral side chain which has made it useful for mapping the shape of the CB2 binding site. It was discovered by, and named after, John W. Huffman.

<span class="mw-page-title-main">JWH-203</span> Chemical compound

JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist with approximately equal affinity at both the CB1 and CB2 receptors, having a Ki of 8.0 nM at CB1 and 7.0 nM at CB2. It was originally discovered by, and named after, John W. Huffman, but has subsequently been sold without his permission as an ingredient of synthetic cannabis smoking blends. Similar to the related 2'-methoxy compound JWH-250, the 2'-bromo compound JWH-249, and the 2'-methyl compound JWH-251, JWH-203 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds, and has the strongest in vitro binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.

<span class="mw-page-title-main">JWH-007</span> Chemical compound

JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was first reported in 1994 by a group including the noted cannabinoid chemist John W. Huffman. It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the N-morpholinylethyl compounds pravadoline (WIN 48,098), JWH-200 (WIN 55,225) and WIN 55,212-2 by the Sterling Winthrop group. Several other N-alkyl substituents were found to be active by Huffman's team including the n-butyl, n-hexyl, 2-heptyl, and cyclohexylethyl groups, but it was subsequently determined that the 2-methyl group on the indole ring is not required for CB1 binding, and tends to increase affinity for CB2 instead. Consequently, the 2-desmethyl derivative of JWH-007, JWH-018, has slightly higher binding affinity for CB1, with an optimum binding of 9.00 nM at CB1 and 2.94 nM at CB2, and JWH-007 displayed optimum binding of 9.50 nM at CB1 and 2.94 nM at CB2.

<span class="mw-page-title-main">JWH-164</span> Chemical compound

JWH-164 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It has approximately equal affinity for the CB1 and CB2 receptors, with a Ki of 6.6 nM at CB1 and 6.9 nM at CB2. JWH-164 is a positional isomer of the related compound JWH-081, but with a methoxy group at the 7-position of the naphthyl ring, rather than the 4-position as in JWH-081. Its potency is intermediate between that of JWH-081 and its ring unsubstituted derivative JWH-018, demonstrating that substitution of the naphthyl 7-position can also result in increased cannabinoid receptor binding affinity.

<span class="mw-page-title-main">JWH-167</span> Chemical compound

JWH-167 (1-pentyl-3-(phenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 1.75 times selectivity for CB1 with a Ki of 90 nM ± 17 and 159 nM ± 14 at CB2. Similar to the related 2'-methoxy compound JWH-250, and the 2'-chloro compound JWH-203, JWH-167 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.

<span class="mw-page-title-main">JWH-249</span> Chemical compound

JWH-249 (1-pentyl-3-(2-bromophenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 2.4 times selectivity for CB1 with a Ki of 8.4 ± 1.8 nM and 20 ± 2 nM at CB2. Similar to the related 2'-methoxy compound JWH-250, the 2'-chloro compound JWH-203, and the 2'-methyl compound JWH-251, JWH-249 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.

<span class="mw-page-title-main">JWH-424</span> Chemical compound

JWH-424 is a drug from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors, but with moderate selectivity for CB2, having a Ki of 5.44nM at CB2 vs 20.9 nM at CB1. The heavier 8-iodo analogue is even more CB2 selective, with its 2-methyl derivative having 40 times selectivity for CB2. However the 1-propyl homologues in this series showed much lower affinity at both receptors, reflecting a generally reduced affinity for the 8-substituted naphthoylindoles overall.

<span class="mw-page-title-main">JWH-120</span> Chemical compound

JWH-120 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-propyl analog of JWH-122. It is a potent and selective ligand for the CB2 receptor, but a weaker ligand for the CB1 receptor. It has a binding affinity of Ki = 6.1 ± 0.7 nM at the CB2 subtype and 173 times selectivity over the CB1 subtype.

<span class="mw-page-title-main">JWH-148</span> Chemical compound

JWH-148 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the indole 2-methyl analog of JWH-120. It is a moderately selective ligand for the CB2 receptor, with a binding affinity of Ki = 14.0 ± 1.0 nM at this subtype, and more than eight times selectivity over the CB1 subtype.

<span class="mw-page-title-main">JWH-149</span> Chemical compound

JWH-149 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-pentyl analog of JWH-148. It is a potent but only moderately selective ligand for the CB2 receptor, with a binding affinity of Ki = 0.73 ± 0.03 nM at this subtype, and more than six times selectivity over the CB1 subtype.

<span class="mw-page-title-main">JWH-371</span> Chemical compound

JWH-371 ([5-(4-butylphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 42 ± 1nM) and CB2 (Ki = 64 ± 2nM) receptors, binding ~1.5 times stronger to the CB1 receptor than the CB2 receptor. JWH-371 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

<span class="mw-page-title-main">JWH-370</span> Chemical compound

JWH-370 ([5-(2-methylphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 5.6 ± 0.4nM) and CB2 (Ki = 4.0 ± 0.5nM) receptors, with a slight selectivity for the CB2 receptor. JWH-370 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

<span class="mw-page-title-main">JWH-368</span> Chemical compound

JWH-368 ([5-(3-Fluorophenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 16 ± 1nM) and CB2 (Ki = 9.1 ± 0.7nM) receptors, binding ~1.76 times stronger to the CB2 receptor than to the CB1 receptor. JWH-368 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

<span class="mw-page-title-main">JWH-366</span> Chemical compound

JWH-366 (naphthalen-1-yl-(1-pentyl-5-pyridin-3-ylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 191 ± 12nM) and CB2 (Ki = 24 ± 1nM) receptors, with a strong (~8x) selectivity for the CB2 receptor over the CB1 receptor. JWH-366 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

<span class="mw-page-title-main">JWH-365</span> Chemical compound

JWH-365 ((5-(2-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 17 ± 1nM) and CB2 (Ki = 3.4 ± 0.2nM) receptors, with a strong (~5x) selectivity for the CB2 receptor over the CB1 receptor. JWH-365 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

<span class="mw-page-title-main">JWH-146</span> Chemical compound

JWH-146 (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 21 ± 2nM) and CB2 (Ki = 62 ± 5nM) receptors, with a moderate (~2.9x) selectivity for the CB1 receptor over the CB2 receptor. JWH-146 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

<span class="mw-page-title-main">JWH-150</span> Chemical compound

JWH-150 ((1-butyl-5-phenylpyrrol-3-yl)-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 60 ± 1nM) and CB2 (Ki = 15 ± 2nM) receptors, with a moderate four-fold selectivity for the CB2 receptor. JWH-150 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 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. 1 2 3 4 5 6 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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 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. 1 2 3 4 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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 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. 1 2 3 4 5 6 7 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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