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HU-331

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to the protein. This molecule does not cause damage to DNA, but protects cells from damage, natural, or induced by other inhibitors of topoisomerase II that act as inhibitors of topoisomerase. Even when 60% of the target cells are killed by treatment with HU-331, other cells' nucleic content remains
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and inhibition of DNA topoisomerase I and II. This leads to breaking the chains of DNA single and double strands. The protein associated with these ruptures are the topoisomerase II and DNA damage is catalyzed by this enzyme. Thus, while doxorubicin and other
510:. Although in some studies. HU-331 has not caused the death of cells by oncogenic apoptosis. The conclusion that would lead cells to apoptosis based on treatment with the drug did not increase the proportion of cells containing 1461: 88: 1781: 1505: 1500: 1495: 1415: 1162: 2773: 1410: 1045: 2768: 2763: 2985: 1429: 1531: 1483: 1434: 1424: 1157: 1543: 1478: 1040: 405:, then inhibiting the catalytic activity of topoisomerase, which hinders the activity of these enzymes without introducing breaks into the DNA chains. HU-331 seems to be a 1550: 897: 1632: 954: 909: 885: 1364: 1352: 1176: 1114: 966: 401:
can act at two different levels. First inhibiting topoisomerase, which stabilize the topoisomerase-DNA complex and thus introduce DNA breaks in the wires that lead to
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Kogan N.M.; et al. (2007). "A Cannabinoid Anticancer Quinone, HU-331, Is More Potent and Less Cardiotoxic Than Doxorubicin: A Comparative in Vivo Study".
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InChI=1S/C21H28O3/c1-5-6-7-8-15-12-18(22)19(21(24)20(15)23)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,24H,2,5-10H2,1,3-4H3/t16-,17+/m0/s1
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in human cancers for many years. The mechanism of action of these drugs has been the subject of considerable controversy since
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and has a specific activity that gives great potential to develop as a new anticancer drug, according to Kogan
5282: 1996: 1566: 1991: 1986: 1981: 1791: 1761: 1405: 144: 2872: 1456: 479: 165: 1018: 800: 747: 4821: 433: 182: 5272: 5243: 4807: 1861: 1796: 1652: 705: 5236: 4151: 2614: 1771: 1526: 730: 450: 437: 716: 4831: 2930: 1836: 1786: 1756: 1743: 1724: 1597: 1538: 1521: 1490: 483: 460:, etc. Hu-331 is more active and less toxic, since it generates reactive oxygen species in the 502:
do not inhibit HU-331, despite being mediated by a cannabinoid receptor. The HU-331 exerts an
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even at nanomolar concentrations, but has shown a negligible effect on the action of DNA
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unharmed, with less breakage of DNA chains that control important cellular functions.
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quinones. One of the main objectives of these studies is the development of a new
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effect on target cells by nonspecific mechanisms. The doxorubicin damages DNA by
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cells followed by direct interaction with cannabinoid receptors. The growth of
358: 284: 550:"HU-331 (3-hydroxy-2--5-pentyl-2,5-cyclohexadiene-1,4-dione)" is a Schedule I 5266: 5005: 4312: 3140: 3135: 2970: 2945: 2506: 2336: 1891: 1657: 1637: 1627: 1622: 1607: 1285: 1080: 932: 539: 454: 442: 398: 682: 4881: 4787: 4719: 4584: 4484: 3246: 3191: 3095: 3060: 3050: 3045: 3040: 3010: 3005: 3000: 2574: 1382: 1330: 1137: 690: 648: 421: 5085: 5080: 4936: 4846: 4841: 4664: 4659: 4579: 4569: 4514: 4509: 4489: 4322: 3442: 3276: 3130: 3115: 2980: 2975: 2808: 2747: 2742: 2717: 2001: 1826: 984: 816: 623:"HU-331, a novel cannabinoid-based anticancer topoisomerase II inhibitor" 495: 417: 340: 336: 5200: 5195: 5190: 5185: 5180: 5175: 5100: 4901: 4896: 4866: 4724: 4609: 4519: 4494: 3402: 3281: 3261: 3226: 3206: 3160: 3015: 2995: 2955: 2849: 2818: 2803: 2691: 2664: 2534: 2011: 1751: 1253: 487: 378: 354: 272: 99: 1816: 498:. The reason behind the antitumor effect of HU-331 appears unknown as 5165: 5160: 5120: 5075: 4861: 4782: 4767: 4704: 4694: 4689: 4604: 4589: 4454: 4414: 4373: 4368: 3867: 3348: 3343: 3312: 3307: 3211: 3181: 2990: 2839: 2834: 2675: 2564: 2559: 2544: 2491: 2486: 2366: 2346: 2341: 2331: 2326: 1976: 1719: 1714: 1647: 567: 522: 471: 429: 406: 402: 350: 283:
Except where otherwise noted, data are given for materials in their
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Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
713:"21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." 87: 5115: 5090: 5040: 5035: 4951: 4906: 4797: 4792: 4757: 4699: 4504: 4499: 4378: 4340: 4241: 4226: 4221: 4216: 4171: 4156: 4125: 4105: 4100: 4095: 4074: 4069: 4053: 4048: 4043: 4038: 4033: 4028: 4023: 4018: 4013: 4008: 4003: 3983: 3973: 3933: 3928: 3923: 3918: 3883: 3847: 3822: 3717: 3712: 3707: 3702: 3692: 3667: 3637: 3632: 3627: 3622: 3617: 3602: 3562: 3537: 3512: 3507: 3482: 3477: 3467: 3452: 3432: 3427: 3422: 3417: 3412: 3407: 3379: 3363: 3317: 3216: 3196: 3055: 2798: 2793: 2727: 2539: 2361: 2301: 2096: 2091: 2086: 2076: 2071: 2066: 2061: 2046: 2036: 2026: 1946: 1941: 1936: 1881: 1876: 578:
HU-331 is included on the list of novel psychoactive substances (
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of the cell cycle cell, activation of caspases, generation of
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activity while maintaining low toxicity at therapeutic doses.
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Cannabinoids can act as anticancer compounds killing several
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making it illegal to buy, sell, or possess in Wisconsin.
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making it illegal to buy, sell, or possess in Florida.
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HU-331 is not scheduled at the federal level in the
373:. The cannabinoid quinone HU-331 is a very specific 1762:
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
453:, inhibition of both topoisomerases, activation of 234:O=C\1C(\O)=C(/C(=O)/C=C/1CCCCC)2\C=C(/CC2\C(=C)C)C 41:3-Hydroxy-2--5-pentylcyclohexa-2,5-diene-1,4-dione 5264: 1827:O-Arachidonoyl ethanolamine (O-AEA; virodhamine) 1782:2-Arachidonoyl lysophosphatidylinositol (2-ALPI) 132: 445:act through many mechanisms such as apoptosis, 420:, like other anticancer quinones, was used for 63: 478:is inhibited by a selective activation of the 377:of topoisomerase II, compared with most known 801: 353:human cells. HU-331 does not cause arrest in 4742: 1752:Arachidonoyl ethanolamide (AEA; anandamide) 409:inhibitor of topoisomerase II, probably by 5251:Designer drugs § Synthetic cannabimimetics 808: 794: 668: 620: 349:plant. It showed a great efficacy against 185: 107: 664: 662: 660: 658: 638: 152: 181: 5265: 655: 392: 789: 521:and have not found the expression of 213:Key: WDXXEUARVHTWQF-DLBZAZTESA-N 385:derived compound that produces anti- 2774:1-Pentyl-3-(2-methoxybenzoyl)indole 506:effect accompanied by apoptosis of 123: 13: 2769:1-Butyl-3-(4-methoxybenzoyl)indole 2764:1-Butyl-3-(2-methoxybenzoyl)indole 1792:Docosatetraenoylethanolamide (DEA) 1787:N-Arachidonoyl serotonin (AA-5-HT) 14: 5294: 2986:AB-FUBINACA 2-fluorobenzyl isomer 815: 621:Kogan N.M.; et al. (2007). 533: 500:cannabinoid receptor antagonists 365:activation. HU-331 inhibits DNA 291: 22: 5228:Cannabinoid receptor modulators 758: 528: 287:(at 25 °C , 100 kPa). 5230:(cannabinoids by pharmacology) 1797:Lysophosphatidylinositol (LPI) 1772:N-Arachidonoyl dopamine (NADA) 1560:Delta-10-Tetrahydrocannabinols 752: 614: 1: 1757:2-Arachidonoylglycerol (2-AG) 1444:Delta-9-tetrahydrocannabinols 1399:Delta-8-tetrahydrocannabinols 759:Kft, Wolters Kluwer Hungary. 640:10.1158/1535-7163.MCT-06-0039 607: 4747:Tooltip Cannabinoid receptor 1777:N-Arachidonylglycine (NAGly) 561: 7: 4932:Palmitoylethanolamide (PEA) 1812:Palmitoylethanolamide (PEA) 585: 277:328.445 g/mol 10: 5299: 2337:Levonantradol (CP 50,5561) 1822:Stearoylethanolamide (SEA) 1576:Miscellaneous cannabinoids 573: 545: 5219: 4990: 4822:4-Nonylphenylboronic acid 4814:(inactivation inhibitors) 4806: 4737: 4402: 4349: 4331: 4305: 4144: 4088: 4062: 3876: 3393: 3372: 3331: 3169: 2911: 2848: 2827: 2756: 2710: 2684: 2520: 1852: 1835: 1742: 1687: 1575: 1559: 1443: 1398: 1375: 1323: 1246: 1230: 1130: 1073: 977: 925: 854: 838: 823: 281: 242: 222: 197: 47: 35: 30: 21: 4922:Oleoylethanolamide (OEA) 1862:1,2-Didehydro-3-oxo-THCO 1807:Oleoylethanolamide (OEA) 1653:Epigallocatechin gallate 480:CB2 cannabinoid receptor 4152:Cannabipiperidiethanone 2878:Methanandamide (AM-356) 1767:2-Oleoylglycerol (2-OG) 683:10.1124/jpet.107.120865 671:J. Pharmacol. Exp. Ther 580:55/2014. EMMI rendelet 484:endogenous cannabinoids 438:reactive oxygen species 5161:Otenabant (CP-945,598) 4832:Arachidonoyl serotonin 2804:GW-405,833 (L-768,242) 1853:Classical cannabinoids 1598:8,9-Dihydrocannabidiol 748:2013 Wisconsin Act 351 335:drug synthesized from 5196:Surinabant (SR147778) 5181:Rimonabant (SR141716) 5071:Dietressa (Диетресса) 5046:Brizantin (Бризантин) 4435:5F-3-pyridinoylindole 4089:Naphthylmethylindoles 4063:Naphthylmethylindenes 3332:Indole-3-carboxylates 3170:Indole-3-carboxamides 1593:7,8-Dihydrocannabinol 494:of cells involved in 5283:Hydroxybenzoquinones 5201:Taranabant (MK-0364) 5086:Ibipinabant (SLV319) 4998:agonists/antibodies) 4996:(antagonists/inverse 4475:Abnormal cannabidiol 4306:Pyrazolecarboxamides 2002:Dexanabinol (HU-211) 552:controlled substance 458:secondary messengers 436:, the generation of 37:Preferred IUPAC name 5186:Rosonabant (E-6776) 5076:Drinabant (AVE1625) 4145:Phenylacetylindoles 2931:4'F-CUMYL-5F-PINACA 2570:Delta-6-Cannabidiol 2530:Cannabicyclohexanol 2352:Nabidrox (Canbisol) 1663:Hexahydrocannabinol 393:Mechanism of action 18: 4550:CUMYL-CH-MEGACLONE 4545:CUMYL-CB-MEGACLONE 4450:5F-CUMYL-PEGACLONE 4420:4CN-CUMYL-BUT7AICA 4334:propanoylindazoles 3373:Naphthoylindazoles 3066:CUMYL-3TMS-PRINACA 3036:Adamantyl-THPINACA 1688:Active metabolites 428:drugs exert their 411:enzymatic ligation 314:Infobox references 16: 5260: 5259: 4999: 4815: 4733: 4732: 4350:Tetramethylcyclo- 4332:Tetramethylcyclo- 3877:Naphthoylpyrroles 3177:4'F-CUMYL-5F-PICA 3031:ADMB-3TMS-PRINACA 2926:4'Cl-CUMYL-PINACA 2828:Cyclohexylphenols 2685:Adamantoylindoles 2502:THC hemisuccinate 1738: 1737: 825:Phytocannabinoids 525:in cancer cells. 508:endothelial cells 322:Chemical compound 320: 319: 166:CompTox Dashboard 89:Interactive image 5290: 5244:JWH cannabinoids 4995: 4992:Anticannabinoids 4813: 4748: 4744: 4540:CUMYL-4CN-B7AICA 4352:propanoylindoles 3395:Naphthoylindoles 3071:CUMYL-4CN-BINACA 1850: 1849: 1744:Endocannabinoids 855:Cannabichromenes 836: 835: 810: 803: 796: 787: 786: 780: 779: 777: 776: 767:. Archived from 756: 750: 745: 739: 734: 728: 727: 725: 724: 709: 703: 702: 666: 653: 652: 642: 627:Mol. Cancer Ther 618: 554:in the state of 426:chemotherapeutic 367:topoisomerase II 333:anticarcinogenic 304: 298: 295: 294: 250:Chemical formula 190: 189: 174: 172: 156: 136: 125: 111: 91: 67: 26: 19: 15: 5298: 5297: 5293: 5292: 5291: 5289: 5288: 5287: 5273:HU cannabinoids 5263: 5262: 5261: 5256: 5237:AM cannabinoids 5215: 4997: 4994: 4986: 4812: 4809: 4808:Endocannabinoid 4802: 4746: 4729: 4555:CUMYL-PEGACLONE 4445:5F-CUMYL-P7AICA 4398: 4351: 4345: 4333: 4327: 4301: 4140: 4084: 4058: 3872: 3389: 3368: 3327: 3165: 3121:MDMB-4en-PINACA 3056:APINACA (AKB48) 3026:ADB-5'Br-PINACA 2961:5F-CUMYL-PINACA 2913: 2907: 2844: 2823: 2752: 2706: 2680: 2522: 2516: 2512:THC-O-phosphate 1855:(dibenzopyrans) 1854: 1845:neocannabinoids 1844: 1842: 1840: 1838: 1831: 1734: 1683: 1571: 1555: 1439: 1394: 1371: 1319: 1242: 1226: 1126: 1069: 973: 921: 850: 827: 819: 814: 784: 783: 774: 772: 757: 753: 746: 742: 735: 731: 722: 720: 711: 710: 706: 667: 656: 619: 615: 610: 588: 576: 564: 548: 536: 531: 395: 371:topoisomerase I 346:Cannabis sativa 323: 316: 311: 310: 309:  ?) 300: 296: 292: 288: 266: 262: 258: 252: 238: 235: 230: 229: 218: 215: 214: 211: 205: 204: 193: 175: 168: 159: 139: 126: 114: 94: 81: 70: 57: 43: 42: 12: 11: 5: 5296: 5286: 5285: 5280: 5275: 5258: 5257: 5255: 5254: 5247: 5240: 5232: 5220: 5217: 5216: 5214: 5213: 5208: 5203: 5198: 5193: 5188: 5183: 5178: 5173: 5168: 5163: 5158: 5153: 5148: 5143: 5138: 5133: 5128: 5123: 5118: 5113: 5108: 5103: 5098: 5093: 5088: 5083: 5078: 5073: 5068: 5063: 5058: 5053: 5048: 5043: 5038: 5033: 5028: 5023: 5018: 5013: 5008: 5002: 5000: 4988: 4987: 4985: 4984: 4979: 4974: 4969: 4964: 4959: 4954: 4949: 4944: 4939: 4934: 4929: 4924: 4919: 4914: 4909: 4904: 4899: 4894: 4889: 4884: 4879: 4874: 4869: 4864: 4859: 4854: 4849: 4844: 4839: 4834: 4829: 4824: 4818: 4816: 4804: 4803: 4801: 4800: 4795: 4790: 4785: 4780: 4775: 4770: 4765: 4760: 4754: 4752: 4735: 4734: 4731: 4730: 4728: 4727: 4722: 4717: 4712: 4707: 4702: 4697: 4692: 4687: 4682: 4677: 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3936: 3931: 3926: 3921: 3916: 3911: 3906: 3901: 3896: 3891: 3886: 3880: 3878: 3874: 3873: 3871: 3870: 3865: 3860: 3855: 3850: 3845: 3840: 3835: 3830: 3825: 3820: 3815: 3810: 3805: 3800: 3795: 3790: 3785: 3780: 3775: 3770: 3765: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3725: 3720: 3715: 3710: 3705: 3700: 3695: 3690: 3685: 3680: 3675: 3670: 3665: 3660: 3655: 3650: 3645: 3640: 3635: 3630: 3625: 3620: 3615: 3610: 3605: 3600: 3595: 3590: 3585: 3580: 3575: 3570: 3565: 3560: 3555: 3550: 3545: 3540: 3535: 3530: 3525: 3520: 3515: 3510: 3505: 3500: 3495: 3490: 3485: 3480: 3475: 3470: 3465: 3460: 3455: 3450: 3445: 3440: 3435: 3430: 3425: 3420: 3415: 3410: 3405: 3399: 3397: 3391: 3390: 3388: 3387: 3382: 3376: 3374: 3370: 3369: 3367: 3366: 3361: 3356: 3354:QUCHIC (BB-22) 3351: 3346: 3341: 3335: 3333: 3329: 3328: 3326: 3325: 3320: 3315: 3310: 3305: 3300: 3295: 3289: 3284: 3279: 3274: 3269: 3264: 3259: 3254: 3249: 3244: 3239: 3234: 3229: 3224: 3219: 3214: 3209: 3204: 3199: 3194: 3189: 3184: 3179: 3173: 3171: 3167: 3166: 3164: 3163: 3158: 3153: 3148: 3143: 3138: 3133: 3128: 3126:MDMB-5Br-INACA 3123: 3118: 3113: 3108: 3103: 3101:CUMYL-THPINACA 3098: 3093: 3091:CUMYL-NBMINACA 3088: 3086:CUMYL-FUBINACA 3083: 3081:CUMYL-CHSINACA 3078: 3076:CUMYL-CBMINACA 3073: 3068: 3063: 3058: 3053: 3048: 3043: 3038: 3033: 3028: 3023: 3021:ADB-4en-PINACA 3018: 3013: 3008: 3003: 2998: 2993: 2988: 2983: 2978: 2973: 2968: 2966:5F-EDMB-PINACA 2963: 2958: 2953: 2948: 2943: 2938: 2933: 2928: 2923: 2921:4F-MDMB-BINACA 2917: 2915: 2909: 2908: 2906: 2905: 2900: 2895: 2890: 2885: 2880: 2875: 2870: 2865: 2860: 2854: 2852: 2846: 2845: 2843: 2842: 2837: 2831: 2829: 2825: 2824: 2822: 2821: 2816: 2811: 2806: 2801: 2796: 2791: 2786: 2781: 2776: 2771: 2766: 2760: 2758: 2757:Benzoylindoles 2754: 2753: 2751: 2750: 2745: 2740: 2735: 2730: 2725: 2720: 2714: 2712: 2711:Benzimidazoles 2708: 2707: 2705: 2704: 2699: 2694: 2688: 2686: 2682: 2681: 2679: 2678: 2673: 2668: 2662: 2657: 2652: 2647: 2642: 2637: 2632: 2627: 2622: 2617: 2612: 2607: 2602: 2597: 2592: 2587: 2582: 2577: 2572: 2567: 2562: 2557: 2555:(C9)-CP 47,497 2552: 2550:(C6)-CP 47,497 2547: 2542: 2537: 2532: 2526: 2524: 2518: 2517: 2515: 2514: 2509: 2504: 2499: 2494: 2489: 2484: 2479: 2474: 2469: 2464: 2459: 2454: 2449: 2444: 2439: 2434: 2429: 2424: 2419: 2414: 2409: 2404: 2399: 2394: 2389: 2384: 2379: 2374: 2369: 2364: 2359: 2354: 2349: 2344: 2339: 2334: 2329: 2324: 2319: 2314: 2309: 2304: 2299: 2294: 2289: 2284: 2279: 2274: 2269: 2264: 2259: 2254: 2249: 2244: 2239: 2234: 2229: 2224: 2219: 2214: 2209: 2204: 2199: 2194: 2189: 2184: 2179: 2174: 2169: 2164: 2159: 2154: 2149: 2144: 2139: 2134: 2129: 2124: 2119: 2114: 2109: 2104: 2099: 2094: 2089: 2084: 2079: 2074: 2069: 2064: 2059: 2054: 2049: 2044: 2039: 2034: 2029: 2024: 2019: 2014: 2009: 2004: 1999: 1994: 1989: 1984: 1979: 1974: 1969: 1964: 1959: 1954: 1949: 1944: 1939: 1934: 1929: 1924: 1919: 1914: 1909: 1904: 1899: 1894: 1889: 1884: 1879: 1874: 1869: 1864: 1858: 1856: 1847: 1833: 1832: 1830: 1829: 1824: 1819: 1814: 1809: 1804: 1799: 1794: 1789: 1784: 1779: 1774: 1769: 1764: 1759: 1754: 1748: 1746: 1740: 1739: 1736: 1735: 1733: 1732: 1727: 1722: 1717: 1712: 1707: 1702: 1697: 1691: 1689: 1685: 1684: 1682: 1681: 1676: 1674:Serinolamide A 1671: 1669:Perrottetinene 1666: 1660: 1655: 1650: 1645: 1640: 1635: 1630: 1625: 1620: 1618:Cannabiglendol 1615: 1610: 1605: 1600: 1595: 1590: 1585: 1579: 1577: 1573: 1572: 1570: 1569: 1563: 1561: 1557: 1556: 1554: 1553: 1548: 1547: 1546: 1536: 1535: 1534: 1524: 1519: 1518: 1517: 1512: 1511: 1510: 1509: 1508: 1503: 1488: 1487: 1486: 1476: 1475: 1474: 1469: 1464: 1447: 1445: 1441: 1440: 1438: 1437: 1432: 1427: 1422: 1421: 1420: 1419: 1418: 1416:Delta-8-THCA-A 1402: 1400: 1396: 1395: 1393: 1392: 1391: 1390: 1379: 1377: 1373: 1372: 1370: 1369: 1368: 1367: 1357: 1356: 1355: 1345: 1340: 1339: 1338: 1327: 1325: 1321: 1320: 1318: 1317: 1316: 1315: 1305: 1304: 1303: 1295: 1294: 1293: 1283: 1282: 1281: 1276: 1271: 1266: 1261: 1250: 1248: 1244: 1243: 1241: 1240: 1234: 1232: 1231:Cannabiphorols 1228: 1227: 1225: 1224: 1219: 1218: 1217: 1216: 1215: 1200: 1199: 1198: 1197: 1196: 1181: 1180: 1179: 1169: 1168: 1167: 1166: 1165: 1155: 1150: 1145: 1134: 1132: 1128: 1127: 1125: 1124: 1119: 1118: 1117: 1107: 1102: 1101: 1100: 1099: 1098: 1093: 1077: 1075: 1074:Cannabielsoins 1071: 1070: 1068: 1067: 1062: 1061: 1060: 1050: 1049: 1048: 1038: 1037: 1036: 1026: 1021: 1016: 1015: 1014: 1004: 999: 994: 993: 992: 981: 979: 975: 974: 972: 971: 970: 969: 959: 958: 957: 947: 942: 941: 940: 929: 927: 926:Cannabicyclols 923: 922: 920: 919: 914: 913: 912: 902: 901: 900: 890: 889: 888: 878: 877: 876: 875: 874: 858: 856: 852: 851: 849: 848: 842: 840: 833: 821: 820: 813: 812: 805: 798: 790: 782: 781: 751: 740: 729: 715:Archived from 704: 677:(2): 646–653. 654: 633:(1): 173–183. 612: 611: 609: 606: 605: 604: 599: 594: 587: 584: 582:) in Hungary. 575: 572: 563: 560: 547: 544: 535: 532: 530: 527: 504:antiangiogenic 443:anthraquinones 399:topoisomerases 397:Inhibitors of 394: 391: 359:cell apoptosis 321: 318: 317: 312: 290: 289: 285:standard state 282: 279: 278: 275: 269: 268: 264: 260: 256: 253: 248: 245: 244: 240: 239: 237: 236: 233: 225: 224: 223: 220: 219: 217: 216: 212: 209: 208: 200: 199: 198: 195: 194: 192: 191: 183:DTXSID10929758 178: 176: 164: 161: 160: 158: 157: 149: 147: 141: 140: 138: 137: 129: 127: 119: 116: 115: 113: 112: 104: 102: 96: 95: 93: 92: 84: 82: 75: 72: 71: 69: 68: 60: 58: 53: 50: 49: 45: 44: 40: 39: 33: 32: 28: 27: 9: 6: 4: 3: 2: 5295: 5284: 5281: 5279: 5276: 5274: 5271: 5270: 5268: 5253: 5252: 5248: 5246: 5245: 5241: 5239: 5238: 5233: 5231: 5229: 5226: 5222: 5221: 5218: 5212: 5209: 5207: 5204: 5202: 5199: 5197: 5194: 5192: 5189: 5187: 5184: 5182: 5179: 5177: 5174: 5172: 5169: 5167: 5164: 5162: 5159: 5157: 5154: 5152: 5149: 5147: 5144: 5142: 5139: 5137: 5134: 5132: 5129: 5127: 5124: 5122: 5119: 5117: 5114: 5112: 5109: 5107: 5104: 5102: 5099: 5097: 5094: 5092: 5089: 5087: 5084: 5082: 5079: 5077: 5074: 5072: 5069: 5067: 5064: 5062: 5059: 5057: 5054: 5052: 5049: 5047: 5044: 5042: 5039: 5037: 5034: 5032: 5029: 5027: 5024: 5022: 5019: 5017: 5014: 5012: 5009: 5007: 5004: 5003: 5001: 4993: 4989: 4983: 4980: 4978: 4975: 4973: 4970: 4968: 4965: 4963: 4960: 4958: 4955: 4953: 4950: 4948: 4945: 4943: 4940: 4938: 4935: 4933: 4930: 4928: 4925: 4923: 4920: 4918: 4915: 4913: 4910: 4908: 4905: 4903: 4900: 4898: 4895: 4893: 4890: 4888: 4885: 4883: 4880: 4878: 4875: 4873: 4870: 4868: 4865: 4863: 4860: 4858: 4855: 4853: 4850: 4848: 4845: 4843: 4840: 4838: 4835: 4833: 4830: 4828: 4825: 4823: 4820: 4819: 4817: 4811: 4805: 4799: 4796: 4794: 4791: 4789: 4786: 4784: 4781: 4779: 4776: 4774: 4771: 4769: 4766: 4764: 4761: 4759: 4756: 4755: 4753: 4751: 4745: 4740: 4736: 4726: 4723: 4721: 4718: 4716: 4713: 4711: 4708: 4706: 4703: 4701: 4698: 4696: 4693: 4691: 4688: 4686: 4683: 4681: 4678: 4676: 4673: 4671: 4668: 4666: 4663: 4661: 4658: 4656: 4653: 4651: 4648: 4646: 4643: 4641: 4638: 4636: 4633: 4631: 4628: 4626: 4623: 4621: 4618: 4616: 4613: 4611: 4608: 4606: 4603: 4601: 4598: 4596: 4593: 4591: 4588: 4586: 4583: 4581: 4578: 4576: 4573: 4571: 4568: 4566: 4563: 4561: 4558: 4556: 4553: 4551: 4548: 4546: 4543: 4541: 4538: 4536: 4533: 4531: 4528: 4526: 4523: 4521: 4518: 4516: 4513: 4511: 4508: 4506: 4503: 4501: 4498: 4496: 4493: 4491: 4488: 4486: 4483: 4481: 4478: 4476: 4473: 4471: 4468: 4466: 4463: 4461: 4458: 4456: 4453: 4451: 4448: 4446: 4443: 4441: 4440:5F-ADB-P7AICA 4438: 4436: 4433: 4431: 4428: 4426: 4423: 4421: 4418: 4416: 4413: 4411: 4408: 4407: 4405: 4401: 4395: 4392: 4390: 4387: 4385: 4382: 4380: 4377: 4375: 4372: 4370: 4367: 4365: 4362: 4360: 4357: 4356: 4354: 4348: 4342: 4339: 4338: 4336: 4330: 4324: 4321: 4319: 4316: 4314: 4313:5F-AB-FUPPYCA 4311: 4310: 4308: 4304: 4298: 4295: 4293: 4290: 4288: 4285: 4283: 4280: 4278: 4275: 4273: 4270: 4268: 4265: 4263: 4260: 4258: 4255: 4253: 4250: 4248: 4245: 4243: 4240: 4238: 4235: 4233: 4230: 4228: 4225: 4223: 4220: 4218: 4215: 4213: 4210: 4208: 4205: 4203: 4200: 4198: 4195: 4193: 4190: 4188: 4185: 4183: 4180: 4178: 4175: 4173: 4170: 4168: 4165: 4163: 4160: 4158: 4155: 4153: 4150: 4149: 4147: 4143: 4137: 4134: 4132: 4129: 4127: 4124: 4122: 4119: 4117: 4114: 4112: 4109: 4107: 4104: 4102: 4099: 4097: 4094: 4093: 4091: 4087: 4081: 4078: 4076: 4073: 4071: 4068: 4067: 4065: 4061: 4055: 4052: 4050: 4047: 4045: 4042: 4040: 4037: 4035: 4032: 4030: 4027: 4025: 4022: 4020: 4017: 4015: 4012: 4010: 4007: 4005: 4002: 4000: 3997: 3995: 3992: 3990: 3987: 3985: 3982: 3980: 3977: 3975: 3972: 3970: 3967: 3965: 3962: 3960: 3957: 3955: 3952: 3950: 3947: 3945: 3942: 3940: 3937: 3935: 3932: 3930: 3927: 3925: 3922: 3920: 3917: 3915: 3912: 3910: 3907: 3905: 3902: 3900: 3897: 3895: 3892: 3890: 3887: 3885: 3882: 3881: 3879: 3875: 3869: 3866: 3864: 3861: 3859: 3856: 3854: 3851: 3849: 3846: 3844: 3841: 3839: 3836: 3834: 3831: 3829: 3826: 3824: 3821: 3819: 3816: 3814: 3811: 3809: 3806: 3804: 3801: 3799: 3796: 3794: 3791: 3789: 3786: 3784: 3781: 3779: 3776: 3774: 3771: 3769: 3766: 3764: 3761: 3759: 3756: 3754: 3751: 3749: 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3724: 3721: 3719: 3716: 3714: 3711: 3709: 3706: 3704: 3701: 3699: 3696: 3694: 3691: 3689: 3686: 3684: 3681: 3679: 3676: 3674: 3671: 3669: 3666: 3664: 3661: 3659: 3656: 3654: 3651: 3649: 3646: 3644: 3641: 3639: 3636: 3634: 3631: 3629: 3626: 3624: 3621: 3619: 3616: 3614: 3611: 3609: 3606: 3604: 3601: 3599: 3596: 3594: 3591: 3589: 3586: 3584: 3581: 3579: 3576: 3574: 3571: 3569: 3566: 3564: 3561: 3559: 3556: 3554: 3551: 3549: 3546: 3544: 3541: 3539: 3536: 3534: 3531: 3529: 3526: 3524: 3521: 3519: 3516: 3514: 3511: 3509: 3506: 3504: 3501: 3499: 3496: 3494: 3491: 3489: 3486: 3484: 3481: 3479: 3476: 3474: 3471: 3469: 3466: 3464: 3461: 3459: 3456: 3454: 3451: 3449: 3446: 3444: 3441: 3439: 3436: 3434: 3431: 3429: 3426: 3424: 3421: 3419: 3416: 3414: 3411: 3409: 3406: 3404: 3401: 3400: 3398: 3396: 3392: 3386: 3383: 3381: 3378: 3377: 3375: 3371: 3365: 3362: 3360: 3359:QUPIC (PB-22) 3357: 3355: 3352: 3350: 3347: 3345: 3342: 3340: 3337: 3336: 3334: 3330: 3324: 3321: 3319: 3316: 3314: 3311: 3309: 3306: 3304: 3301: 3299: 3296: 3293: 3290: 3288: 3285: 3283: 3280: 3278: 3275: 3273: 3270: 3268: 3267:CUMYL-5F-PICA 3265: 3263: 3260: 3258: 3255: 3253: 3250: 3248: 3245: 3243: 3240: 3238: 3235: 3233: 3230: 3228: 3225: 3223: 3220: 3218: 3215: 3213: 3210: 3208: 3205: 3203: 3200: 3198: 3195: 3193: 3190: 3188: 3185: 3183: 3180: 3178: 3175: 3174: 3172: 3168: 3162: 3159: 3157: 3154: 3152: 3149: 3147: 3144: 3142: 3141:MDMB-FUBINACA 3139: 3137: 3136:MDMB-CHMINACA 3134: 3132: 3129: 3127: 3124: 3122: 3119: 3117: 3114: 3112: 3109: 3107: 3106:CUMYL-TSINACA 3104: 3102: 3099: 3097: 3094: 3092: 3089: 3087: 3084: 3082: 3079: 3077: 3074: 3072: 3069: 3067: 3064: 3062: 3059: 3057: 3054: 3052: 3049: 3047: 3044: 3042: 3039: 3037: 3034: 3032: 3029: 3027: 3024: 3022: 3019: 3017: 3014: 3012: 3009: 3007: 3004: 3002: 2999: 2997: 2994: 2992: 2989: 2987: 2984: 2982: 2979: 2977: 2974: 2972: 2971:5F-EMB-PINACA 2969: 2967: 2964: 2962: 2959: 2957: 2954: 2952: 2949: 2947: 2946:5F-ADB-PINACA 2944: 2942: 2939: 2937: 2934: 2932: 2929: 2927: 2924: 2922: 2919: 2918: 2916: 2910: 2904: 2901: 2899: 2896: 2894: 2891: 2889: 2886: 2884: 2881: 2879: 2876: 2874: 2871: 2869: 2866: 2864: 2861: 2859: 2856: 2855: 2853: 2851: 2847: 2841: 2838: 2836: 2833: 2832: 2830: 2826: 2820: 2817: 2815: 2812: 2810: 2807: 2805: 2802: 2800: 2797: 2795: 2792: 2790: 2787: 2785: 2782: 2780: 2777: 2775: 2772: 2770: 2767: 2765: 2762: 2761: 2759: 2755: 2749: 2746: 2744: 2741: 2739: 2736: 2734: 2731: 2729: 2726: 2724: 2721: 2719: 2716: 2715: 2713: 2709: 2703: 2700: 2698: 2695: 2693: 2690: 2689: 2687: 2683: 2677: 2674: 2672: 2669: 2666: 2663: 2661: 2658: 2656: 2653: 2651: 2648: 2646: 2643: 2641: 2638: 2636: 2633: 2631: 2628: 2626: 2623: 2621: 2618: 2616: 2613: 2611: 2608: 2606: 2603: 2601: 2598: 2596: 2593: 2591: 2588: 2586: 2583: 2581: 2578: 2576: 2573: 2571: 2568: 2566: 2563: 2561: 2558: 2556: 2553: 2551: 2548: 2546: 2543: 2541: 2538: 2536: 2533: 2531: 2528: 2527: 2525: 2521:Non-classical 2519: 2513: 2510: 2508: 2507:THC-O-acetate 2505: 2503: 2500: 2498: 2495: 2493: 2490: 2488: 2485: 2483: 2480: 2478: 2475: 2473: 2470: 2468: 2465: 2463: 2460: 2458: 2455: 2453: 2450: 2448: 2445: 2443: 2440: 2438: 2435: 2433: 2430: 2428: 2425: 2423: 2420: 2418: 2415: 2413: 2410: 2408: 2405: 2403: 2400: 2398: 2395: 2393: 2390: 2388: 2385: 2383: 2380: 2378: 2375: 2373: 2370: 2368: 2365: 2363: 2360: 2358: 2355: 2353: 2350: 2348: 2345: 2343: 2340: 2338: 2335: 2333: 2330: 2328: 2325: 2323: 2320: 2318: 2315: 2313: 2310: 2308: 2305: 2303: 2300: 2298: 2295: 2293: 2290: 2288: 2285: 2283: 2280: 2278: 2275: 2273: 2270: 2268: 2265: 2263: 2260: 2258: 2255: 2253: 2250: 2248: 2245: 2243: 2240: 2238: 2235: 2233: 2230: 2228: 2225: 2223: 2220: 2218: 2215: 2213: 2210: 2208: 2205: 2203: 2200: 2198: 2195: 2193: 2190: 2188: 2185: 2183: 2180: 2178: 2175: 2173: 2170: 2168: 2165: 2163: 2160: 2158: 2155: 2153: 2150: 2148: 2145: 2143: 2140: 2138: 2135: 2133: 2130: 2128: 2125: 2123: 2120: 2118: 2115: 2113: 2110: 2108: 2105: 2103: 2100: 2098: 2095: 2093: 2090: 2088: 2085: 2083: 2080: 2078: 2075: 2073: 2070: 2068: 2065: 2063: 2060: 2058: 2055: 2053: 2050: 2048: 2045: 2043: 2040: 2038: 2035: 2033: 2030: 2028: 2025: 2023: 2020: 2018: 2015: 2013: 2010: 2008: 2005: 2003: 2000: 1998: 1995: 1993: 1990: 1988: 1985: 1983: 1980: 1978: 1975: 1973: 1970: 1968: 1965: 1963: 1960: 1958: 1955: 1953: 1950: 1948: 1945: 1943: 1940: 1938: 1935: 1933: 1930: 1928: 1925: 1923: 1920: 1918: 1915: 1913: 1910: 1908: 1905: 1903: 1900: 1898: 1895: 1893: 1892:Ajulemic acid 1890: 1888: 1885: 1883: 1880: 1878: 1875: 1873: 1870: 1868: 1865: 1863: 1860: 1859: 1857: 1851: 1848: 1846: 1834: 1828: 1825: 1823: 1820: 1818: 1815: 1813: 1810: 1808: 1805: 1803: 1800: 1798: 1795: 1793: 1790: 1788: 1785: 1783: 1780: 1778: 1775: 1773: 1770: 1768: 1765: 1763: 1760: 1758: 1755: 1753: 1750: 1749: 1747: 1745: 1741: 1731: 1728: 1726: 1723: 1721: 1718: 1716: 1713: 1711: 1708: 1706: 1705:8,11-DiOH-THC 1703: 1701: 1698: 1696: 1693: 1692: 1690: 1686: 1680: 1677: 1675: 1672: 1670: 1667: 1664: 1661: 1659: 1658:Gallocatechol 1656: 1654: 1651: 1649: 1646: 1644: 1641: 1639: 1638:Caryophyllene 1636: 1634: 1631: 1629: 1626: 1624: 1621: 1619: 1616: 1614: 1611: 1609: 1608:Cannabicitran 1606: 1604: 1601: 1599: 1596: 1594: 1591: 1589: 1588:Δ4(8)-iso-THC 1586: 1584: 1581: 1580: 1578: 1574: 1568: 1565: 1564: 1562: 1558: 1552: 1549: 1545: 1542: 1541: 1540: 1537: 1533: 1530: 1529: 1528: 1525: 1523: 1520: 1516: 1513: 1507: 1504: 1502: 1499: 1498: 1497: 1494: 1493: 1492: 1489: 1485: 1482: 1481: 1480: 1477: 1473: 1470: 1468: 1465: 1463: 1460: 1459: 1458: 1455: 1454: 1452: 1449: 1448: 1446: 1442: 1436: 1433: 1431: 1428: 1426: 1423: 1417: 1414: 1413: 1412: 1409: 1408: 1407: 1404: 1403: 1401: 1397: 1389: 1386: 1385: 1384: 1381: 1380: 1378: 1376:Cannabivarins 1374: 1366: 1363: 1362: 1361: 1358: 1354: 1351: 1350: 1349: 1346: 1344: 1341: 1337: 1334: 1333: 1332: 1329: 1328: 1326: 1324:Cannabitriols 1322: 1314: 1311: 1310: 1309: 1306: 1302: 1299: 1298: 1296: 1292: 1289: 1288: 1287: 1284: 1280: 1277: 1275: 1272: 1270: 1267: 1265: 1262: 1260: 1257: 1256: 1255: 1252: 1251: 1249: 1245: 1239: 1236: 1235: 1233: 1229: 1223: 1220: 1214: 1211: 1210: 1209: 1206: 1205: 1204: 1201: 1195: 1192: 1191: 1190: 1187: 1186: 1185: 1182: 1178: 1175: 1174: 1173: 1170: 1164: 1161: 1160: 1159: 1156: 1154: 1151: 1149: 1146: 1144: 1141: 1140: 1139: 1136: 1135: 1133: 1131:Cannabigerols 1129: 1123: 1120: 1116: 1113: 1112: 1111: 1108: 1106: 1103: 1097: 1094: 1092: 1089: 1088: 1087: 1084: 1083: 1082: 1079: 1078: 1076: 1072: 1066: 1063: 1059: 1056: 1055: 1054: 1051: 1047: 1044: 1043: 1042: 1039: 1035: 1032: 1031: 1030: 1027: 1025: 1022: 1020: 1017: 1013: 1010: 1009: 1008: 1005: 1003: 1000: 998: 995: 991: 988: 987: 986: 983: 982: 980: 976: 968: 965: 964: 963: 960: 956: 953: 952: 951: 948: 946: 943: 939: 936: 935: 934: 931: 930: 928: 924: 918: 915: 911: 908: 907: 906: 903: 899: 896: 895: 894: 891: 887: 884: 883: 882: 879: 873: 870: 869: 868: 865: 864: 863: 860: 859: 857: 853: 847: 844: 843: 841: 839:Cannabibutols 837: 834: 831: 826: 822: 818: 811: 806: 804: 799: 797: 792: 791: 788: 771:on 2020-08-08 770: 766: 765:net.jogtar.hu 762: 755: 749: 744: 738: 733: 719:on 2009-08-27 718: 714: 708: 700: 696: 692: 688: 684: 680: 676: 672: 665: 663: 661: 659: 650: 646: 641: 636: 632: 628: 624: 617: 613: 603: 600: 598: 595: 593: 590: 589: 583: 581: 571: 569: 559: 557: 553: 543: 541: 540:United States 534:United States 526: 524: 520: 516: 513: 509: 505: 501: 497: 493: 492:proliferation 489: 485: 481: 477: 473: 468: 467: 463: 459: 456: 455:intracellular 452: 448: 444: 439: 435: 434:intercalation 431: 427: 423: 419: 415: 412: 408: 404: 400: 390: 388: 384: 380: 376: 372: 368: 364: 360: 356: 352: 348: 347: 342: 338: 334: 331: 327: 315: 308: 303: 286: 280: 276: 274: 271: 270: 254: 251: 247: 246: 241: 232: 231: 228: 221: 207: 206: 203: 196: 188: 184: 180: 179: 177: 167: 163: 162: 155: 151: 150: 148: 146: 143: 142: 135: 131: 130: 128: 122: 118: 117: 110: 106: 105: 103: 101: 98: 97: 90: 86: 85: 83: 79: 74: 73: 66: 62: 61: 59: 56: 52: 51: 46: 38: 34: 29: 25: 20: 5278:Cyclohexenes 5249: 5242: 5234: 5224: 5223: 4882:JNJ-42165279 4788:Pregnenolone 4720:WIN 55,212-2 4565:GSK-554,418A 4485:ADB-FUBHQUCA 4430:5F-PY-PINACA 3257:CUMYL-NBMICA 3252:CUMYL-CHMICA 3247:CUMYL-CBMICA 3192:5F-MDMB-PICA 3187:5F-EDMB-PICA 3111:EMB-FUBINACA 3096:CUMYL-PINACA 3061:APP-FUBINACA 3051:AMB-FUBINACA 3046:AMB-CHMINACA 3041:ADSB-FUB-187 3011:ADB-FUBINACA 3006:ADB-HEXINACA 3001:ADB-CHMINACA 2914:carboxamides 2584: 2575:Etrinabdione 2523:cannabinoids 1997:Delta-10-THC 1872:9-Nor-9β-HHC 1730:11-OH-Δ9-THC 1725:11-OH-Δ8-THC 1567:Delta-10-THC 1435:Delta-8-THCV 1430:Delta-8-THCP 1425:Delta-8-THCB 1411:Delta-8-THCA 978:Cannabidiols 817:Cannabinoids 773:. Retrieved 769:the original 764: 754: 743: 732: 721:. Retrieved 717:the original 707: 674: 670: 630: 626: 616: 579: 577: 565: 549: 537: 529:Legal status 490:inhibit the 469: 465: 422:chemotherapy 416: 396: 344: 325: 324: 48:Identifiers 5081:Hemopressin 4937:PF-04457845 4877:JNJ 1661010 4847:Biochanin A 4842:BIA 10-2474 4665:PSB-SB-1202 4660:PF-03550096 4580:LASSBio-881 4570:GW-842,166X 4515:BAY 59-3074 4510:BAY 38-7271 4490:ADB-FUBIATA 4323:AB-CHFUPYCA 3443:FUB-JWH-018 3277:MDMB-CHMICA 3131:MDMB-BINACA 3116:FUB-APINACA 2981:AB-FUBINACA 2976:AB-CHMINACA 2936:5Cl-APINACA 2912:Indazole-3- 2850:Eicosanoids 2809:Pravadoline 2748:RQ-00202730 2743:PF-03550096 2718:AZ-11713908 1992:Delta-7-THC 1987:Delta-4-THC 1982:Delta-3-THC 1839:cannabinoid 1710:11-COOH-THC 1648:Alkylamides 1451:Delta-9-THC 1406:Delta-8-THC 1247:Cannabinols 517:in the sub- 496:lung cancer 418:Doxorubicin 341:cannabinoid 337:cannabidiol 243:Properties 65:137252-25-6 5267:Categories 5191:SR-144,528 5176:PSB-SB-487 5126:NIDA-41020 5101:LY-320,135 4902:LY-2183240 4897:Kaempferol 4867:Guineesine 4739:Allosteric 4725:WIN 56,098 4610:NESS-040C5 4520:BzODZ-EPyr 4495:ADB-P7AICA 4425:5F-PY-PICA 4364:5Cl-UR-144 4359:5Br-UR-144 4318:5F-AMPPPCA 3403:5F-JWH-398 3282:MMB-CHMICA 3262:CUMYL-PICA 3242:CUMYL-BICA 3227:ADB-FUBICA 3207:5F-SDB-006 3161:THQ-PINACA 3016:ADB-PINACA 2996:ADB-BINACA 2956:5F-APINACA 2819:WIN 54,461 2665:Onternabez 2535:Cannabinor 2012:Dronabinol 1843:agonists / 1583:Δ8-iso-THC 830:comparison 775:2021-12-02 723:2014-12-17 608:References 488:anandamide 447:abrogation 387:neoplastic 379:anticancer 355:cell cycle 273:Molar mass 154:I7Q196L4AU 100:ChemSpider 76:3D model ( 55:CAS Number 5235:List of: 5225:See also: 5166:PF-514273 5121:NESS-0327 5051:CAY-10508 4862:Genistein 4857:CAY-10429 4852:CAY-10401 4810:enhancers 4783:PSNCBAM-1 4778:Org 29647 4773:Org 27759 4768:Org 27569 4705:Tedalinab 4695:S-777,469 4690:S-444,823 4605:MEPIRAPIM 4590:Leelamine 4460:A-955,840 4455:A-836,339 4415:4-HTMPIPO 4374:A-834,735 4369:A-796,260 3868:NE-CHMIMO 3349:FUB-PB-22 3344:FDU-PB-22 3313:Org 28611 3308:Org 28312 3212:AB-FUBICA 3182:5F-ADBICA 2991:AB-PINACA 2840:CP-55,940 2835:CP-47,947 2692:5F-AKB-48 2676:Tinabinol 2565:CP 55,940 2560:CP 55,244 2545:CP 47,497 2492:Pirnabine 2487:Parahexyl 2367:Naboctate 2347:Nabazenil 2342:Menabitan 2332:L-759,656 2327:L-759,633 1977:CP 42,096 1837:Synthetic 1720:11-OH-HHC 1715:11-OH-CBN 1695:3'-OH-THC 1506:THCA-B-C1 1501:THCA-A-C1 568:Wisconsin 562:Wisconsin 523:caspase-3 472:oncogenic 430:cytotoxic 407:catalytic 403:apoptosis 375:inhibitor 351:oncogenic 5206:TM-38837 4655:Olorinab 4575:JTE 7-31 4535:CBS-0550 4470:A-PONASA 4465:A-PBITMO 4410:2F-QMPSB 3863:MAM-2201 3858:MAM-1220 3438:EAM-2201 3385:THJ-2201 3339:5F-PB-22 3287:MMB-2201 3272:FDU-NNE1 2733:FUBIMINA 2723:AZD-1940 2667:(HU-308) 2620:Nonabine 2357:Nabilone 1952:AM-11245 1867:9-OH-HHC 1841:receptor 1802:Oleamide 1700:7-OH-CBD 1679:Yangonin 699:31988340 691:17478614 649:17237277 586:See also 519:G1 phase 486:such as 5116:MK-9470 5091:JTE-907 5041:BML-190 5036:AM-6545 5031:AM-6527 5026:AM-4113 5021:AM-1387 4977:URB-754 4972:URB-602 4967:URB-597 4962:URB-447 4952:PF-3845 4927:Olvanil 4907:MK-4409 4837:Arvanil 4798:ZCZ-011 4793:RTI-371 4758:AEF0117 4750:ligands 4710:URB-447 4700:SER-601 4505:AM-1714 4500:AM-1248 4379:FUB-144 4341:FAB-144 4292:JWH-316 4287:JWH-315 4282:JWH-314 4277:JWH-313 4272:JWH-312 4267:JWH-311 4262:JWH-306 4257:JWH-305 4252:JWH-304 4247:JWH-303 4242:JWH-302 4237:JWH-253 4232:JWH-252 4227:JWH-251 4222:JWH-250 4217:JWH-249 4212:JWH-248 4207:JWH-237 4202:JWH-209 4197:JWH-208 4192:JWH-207 4187:JWH-206 4182:JWH-205 4177:JWH-204 4172:JWH-203 4167:JWH-202 4162:JWH-201 4157:JWH-167 4136:JWH-199 4131:JWH-197 4126:JWH-196 4121:JWH-195 4116:JWH-194 4111:JWH-192 4106:JWH-185 4101:JWH-184 4096:JWH-175 4080:JWH-220 4075:JWH-176 4070:JWH-171 4054:JWH-373 4049:JWH-372 4044:JWH-371 4039:JWH-370 4034:JWH-369 4029:JWH-368 4024:JWH-367 4019:JWH-366 4014:JWH-365 4009:JWH-364 4004:JWH-363 3999:JWH-348 3994:JWH-347 3989:JWH-346 3984:JWH-309 3979:JWH-308 3974:JWH-307 3969:JWH-293 3964:JWH-292 3959:JWH-246 3954:JWH-245 3949:JWH-244 3944:JWH-243 3939:JWH-156 3934:JWH-150 3929:JWH-147 3924:JWH-146 3919:JWH-145 3914:JWH-045 3909:JWH-044 3904:JWH-036 3899:JWH-033 3894:JWH-032 3889:JWH-031 3884:JWH-030 3853:JWH-425 3848:JWH-424 3843:JWH-423 3838:JWH-422 3833:JWH-417 3828:JWH-416 3823:JWH-398 3818:JWH-387 3813:JWH-268 3808:JWH-267 3803:JWH-266 3798:JWH-265 3793:JWH-262 3788:JWH-261 3783:JWH-260 3778:JWH-259 3773:JWH-258 3768:JWH-242 3763:JWH-241 3758:JWH-240 3753:JWH-239 3748:JWH-236 3743:JWH-235 3738:JWH-234 3733:JWH-213 3728:JWH-212 3723:JWH-211 3718:JWH-210 3713:JWH-200 3708:JWH-198 3703:JWH-193 3698:JWH-189 3693:JWH-182 3688:JWH-181 3683:JWH-180 3678:JWH-166 3673:JWH-165 3668:JWH-164 3663:JWH-163 3658:JWH-160 3653:JWH-159 3648:JWH-153 3643:JWH-151 3638:JWH-149 3633:JWH-148 3628:JWH-122 3623:JWH-120 3618:JWH-116 3613:JWH-100 3608:JWH-099 3603:JWH-098 3598:JWH-097 3593:JWH-096 3588:JWH-095 3583:JWH-094 3578:JWH-093 3573:JWH-083 3568:JWH-082 3563:JWH-081 3558:JWH-080 3553:JWH-079 3548:JWH-077 3543:JWH-076 3538:JWH-073 3533:JWH-072 3528:JWH-070 3523:JWH-050 3518:JWH-049 3513:JWH-048 3508:JWH-047 3503:JWH-046 3498:JWH-043 3493:JWH-042 3488:JWH-020 3483:JWH-019 3478:JWH-018 3473:JWH-016 3468:JWH-015 3463:JWH-011 3458:JWH-009 3453:JWH-007 3448:JWH-004 3433:CHM-081 3428:AM-2232 3423:AM-2201 3418:AM-1235 3413:AM-1221 3408:AM-1220 3380:THJ-018 3364:NM-2201 3323:STS-135 3318:SDB-006 3294:(UR-12) 3217:AB-PICA 3197:5F-NNE1 2863:AM-1346 2799:AM-2233 2794:AM-1241 2728:BIM-018 2702:STS-135 2671:SPA-229 2615:HUF-101 2540:CBD-DMH 2362:Nabitan 2317:JWH-362 2312:JWH-361 2307:JWH-360 2302:JWH-359 2297:JWH-358 2292:JWH-357 2287:JWH-356 2282:JWH-355 2277:JWH-354 2272:JWH-353 2267:JWH-352 2262:JWH-350 2257:JWH-349 2252:JWH-341 2247:JWH-340 2242:JWH-339 2237:JWH-338 2232:JWH-336 2227:JWH-310 2222:JWH-301 2217:JWH-300 2212:JWH-299 2207:JWH-298 2202:JWH-278 2197:JWH-277 2192:JWH-256 2187:JWH-254 2182:JWH-247 2177:JWH-233 2172:JWH-230 2167:JWH-229 2162:JWH-227 2157:JWH-226 2152:JWH-225 2147:JWH-224 2142:JWH-217 2137:JWH-216 2132:JWH-215 2127:JWH-191 2122:JWH-190 2117:JWH-189 2112:JWH-188 2107:JWH-187 2102:JWH-186 2097:JWH-161 2092:JWH-143 2087:JWH-142 2082:JWH-139 2077:JWH-138 2072:JWH-133 2067:JWH-130 2062:JWH-124 2057:JWH-103 2052:JWH-102 2047:JWH-091 2042:JWH-065 2037:JWH-057 2032:JWH-056 2027:JWH-051 1947:AM-7438 1942:AM-4030 1937:AM-2389 1887:A-42574 1882:A-41988 1877:A-40174 1817:RVD-Hpα 1496:THCA-C1 1484:THCA-C4 1213:CBGVA-A 1194:CBNRA-A 574:Hungary 556:Florida 546:Florida 383:quinone 363:caspase 343:in the 330:quinone 307:what is 305: ( 267: 121:PubChem 109:9568213 17:HU-331 5171:PipISB 5156:O-2654 5151:O-2050 5146:O-1918 5141:O-1248 5136:O-1184 5106:MDA-77 5016:AM-630 5011:AM-281 5006:AM-251 4982:VDM-11 4947:PF-750 4942:PF-622 4917:O-2093 4912:O-1624 4892:JZL195 4887:JZL184 4827:AM-404 4763:GAT100 4715:VSN-16 4650:O-2220 4645:O-1602 4640:O-1399 4635:O-1270 4630:O-1269 4615:NMDMSB 4600:MDA-19 4560:EG-018 4480:AB-001 4403:Others 4394:XLR-12 4389:XLR-11 4384:UR-144 3222:ADBICA 3202:5F-PCN 2951:5F-AMB 2941:5F-ADB 2903:O-1861 2898:O-1860 2893:O-1812 2858:AM-883 2789:AM-694 2784:AM-679 2779:AM-630 2738:MCHB-1 2660:O-1871 2655:O-1663 2650:O-1660 2645:O-1657 2640:O-1656 2635:O-1601 2630:O-1422 2625:O-1376 2610:HU-910 2605:HU-465 2600:HU-446 2595:HU-345 2590:HU-336 2585:HU-331 2580:HU-320 2497:SP-111 2482:O-3226 2477:O-3223 2472:O-2716 2467:O-2715 2462:O-2694 2457:O-2545 2452:O-2484 2447:O-2426 2442:O-2383 2437:O-2373 2432:O-2372 2427:O-2365 2422:O-2113 2417:O-2048 2412:O-1238 2407:O-1191 2402:O-1125 2397:O-1057 2322:KM-233 2022:HU-243 2017:HU-210 1972:AMG-41 1967:AMG-36 1932:AM-938 1927:AM-926 1922:AM-919 1917:AM-906 1912:AM-905 1907:AM-855 1902:AM-411 1897:AM-087 1472:THCA-B 1467:THCA-A 1453:(THC) 1274:CBN-C4 1269:CBN-C2 1264:CBN-C1 1096:CBEA-B 1091:CBEA-A 1002:CBD-C5 997:CBD-C1 872:CBCA-A 697:  689:  647:  602:HU-336 597:HU-320 592:HU-345 476:glioma 466:et al. 326:HU-331 302:verify 299:  227:SMILES 134:126249 31:Names 5211:VCHSR 5131:O-606 5111:MJ-15 5096:LH-21 5066:CB-86 5061:CB-52 5056:CB-25 4685:QMPSB 4680:PTI-3 4675:PTI-2 4670:PTI-1 4625:O-889 4620:NMP-7 4595:MDA-7 4585:LBP-1 4530:CB-86 4525:CB-13 4297:RCS-8 3292:MN-25 3237:BMS-F 3232:APICA 3146:MN-18 2888:O-689 2883:O-585 2814:RCS-4 2697:APICA 2392:O-823 2387:O-806 2382:O-774 2377:O-581 2372:O-224 1962:AMG-3 1957:AMG-1 1665:(HHC) 1633:CBRPA 1544:THCVA 1532:THCPA 1479:THCBA 1462:THCMA 1365:CBTPA 1353:CBTVA 1313:CBVDA 1301:CBNPA 1297:CBNP 1291:CBNDA 1208:CBGVA 1189:CBNRA 1177:CBGPA 1163:CBGAM 1153:CBGBA 1115:CBEPA 1058:CBDVA 1046:CBDMA 1034:CBDPA 1012:CBDBA 967:CBLVA 955:CBLPA 910:CBCVA 898:CBCPA 886:CBCBA 695:S2CID 462:heart 328:is a 202:InChI 78:JSmol 4957:PHOP 4872:IDFP 3303:PX-1 3298:NNE1 3156:PX-3 3151:PX-2 2873:ACPA 2868:ACEA 2007:DMHP 1643:DCBF 1603:CBCF 1551:THCQ 1539:THCV 1527:THCP 1522:THCH 1515:THCB 1491:THCC 1457:THCA 1388:CBVA 1360:CBTP 1348:CBTV 1343:CBTB 1336:CBTA 1308:CBVD 1286:CBND 1279:CBNM 1259:CBNA 1222:CBGQ 1203:CBGV 1184:CBNR 1172:CBGP 1158:CBGM 1148:CBGB 1143:CBGA 1122:CBEV 1110:CBEP 1105:CBEB 1086:CBEA 1065:CBDQ 1053:CBDV 1041:CBDM 1029:CBDP 1024:CBDH 1019:CBDD 1007:CBDB 990:CBDA 962:CBLV 950:CBLP 945:CBLB 938:CBLA 917:CBCQ 905:CBCV 893:CBCP 881:CBCB 867:CBCA 687:PMID 645:PMID 515:Lues 482:and 339:, a 145:UNII 4743:CBR 1628:CBR 1623:CBM 1613:CBF 1383:CBV 1331:CBT 1254:CBN 1238:CBP 1138:CBG 1081:CBE 985:CBD 933:CBL 862:CBC 846:CBB 679:doi 675:322 635:doi 512:DNA 451:ROS 361:or 171:EPA 124:CID 5269:: 763:. 693:. 685:. 673:. 657:^ 643:. 629:. 625:. 542:. 357:, 261:28 257:21 832:) 828:( 809:e 802:t 795:v 778:. 726:. 701:. 681:: 651:. 637:: 631:6 297:Y 265:3 263:O 259:H 255:C 173:) 169:( 80:)

Index


Preferred IUPAC name
CAS Number
137252-25-6
JSmol
Interactive image
ChemSpider
9568213
PubChem
126249
UNII
I7Q196L4AU
CompTox Dashboard
DTXSID10929758
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
standard state
verify
what is
Infobox references
quinone
anticarcinogenic
cannabidiol
cannabinoid
Cannabis sativa
oncogenic
cell cycle

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