Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Δ9-tetrahydrocannabinol

Drug and Alcohol Dependence

Volumn 112, Issue 1-2, 2010, Pages 126-133

  DeLong, Gerald T ^a   Wolf, Carl E ^a   Poklis, Alphonse ^a   Lichtman, Aron H ^a,b  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^b Uniformed Services University of the Health Sciences and the Walter Reed National Military Medical Center   (United States)

Author keywords

Anti inflammatory; Cannabichromene; Cannabis sativa; CB1 cannabinoid receptor; CB2 cannabinoid receptor; Delta 9 tetrahydrocannabinol (THC); Marijuana; Phytocannabinoid

Indexed keywords

5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; CANNABICHROMENE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABIS; DRONABINOL; LIPOPOLYSACCHARIDE; RIMONABANT;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTINOCICEPTION; ARTICLE; CATALEPSY; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG DOSE COMPARISON; DRUG MECHANISM; DRUG POTENTIATION; HYPOTHERMIA; MALE; MOTOR RETARDATION; MOUSE; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BORNANES; CANNABINOIDS; CANNABIS; CATALEPSY; DOSE-RESPONSE RELATIONSHIP, DRUG; HALLUCINOGENS; HYPOTHERMIA; INFLAMMATION; MALE; MICE; MICE, INBRED ICR; MOTOR ACTIVITY; PIPERIDINES; PYRAZOLES; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; TETRAHYDROCANNABINOL;

CANNABIS SATIVA;

EID: 78049362246     PISSN: 03768716     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.drugalcdep.2010.05.019     Document Type: Article

References (50)

1. Booker L., Naidu P.S., Razdan R.K., Mahadevan A., Lichtman A.H. Evaluation of prevalent phytocannabinoids in the acetic acid model of visceral nociception. Drug Alcohol Depend. 2009, 105:42-47.
2. Brown N.K., Harvey D.J. In vitro metabolism of cannabichromene in seven common laboratory animals. Drug Metab. Dispos. 1990, 18:1065-1070.
3. 1-tetrahydrocannabinol action by its metabolites. Biochem. Pharmacol. 1986, 35:2553-2558.
4. Compton D.R., Rice K.C., De Costa B.R., Razdan R.K., Melvin L.S., Johnson M.R., Martin B.R. Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J. Pharmacol. Exp. Ther. 1993, 265:218-226.
5. 9-tetrahdrocannabinol-induced responses and apparent agonist activity. J. Pharmacol. Exp. Ther. 1996, 277:586-594.
6. Costa B., Giagnoni G., Franke C., Trovato A.E., Colleoni M. Vanilloid TRPV1 receptor mediates the antihyperalgesic effect of the nonpsychoactive cannabinoid, cannabidiol, in a rat model of acute inflammation. Br. J. Pharmacol. 2004, 143:247-250.
7. Costa B., Trovato A.E., Comelli F., Giagnoni G., Colleoni M. The non-psychoactive cannabis constituent cannabidiol is an orally effective therapeutic agent in rat chronic inflammatory and neuropathic pain. Eur. J. Pharmacol. 2007, 556:75-83.
8. Croxford J.L., Yamamura T. Cannabinoids and the immune system: potential for the treatment of inflammatory diseases?. J. Neuroimmunol. 2005, 166:3-18.
9. D'Amour F.E., Smith D.L. A method for determining loss of pain sensation. J Pharm Exp Ther 1941, 72:74-79.
10. 9-tetrahydrocannabinol. Gen. Pharmacol. 1983, 14:247-252.
11. 6-THC-7-oic acid. Agents Actions 1990, 31:157-163.
12. ElSohly M.A., Slade D. Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci. 2005, 78:539-548.
13. Fan F., Compton D., Ward S., Melvin L., Martin B. Development of cross-tolerance between delta 9-tetrahydrocannabinol CP 55,940 and WIN 55,212. J. Pharmacol. Exp. Ther. 1994, 271:1383-1390.
14. Fride E. Behavioral methods in cannabinoid research. Methods Mol. Med. 2006, 123:269-290.
15. Gaoni Y., Mechoulam R. Isolation, structure, and partial synthesis of an active constituent of hashish. J. Am. Chem. Soc. 1964, 86:1646-1647.
16. Gaoni Y., Mechoulam R. Cannabichromene, a new active principle in hashish. Chem. Commun. 1966, 1:20-21.
17. Gaoni Y., Mechoulam R. The isolation and structure of delta-1-tetrahydrocannabinol and other neutral cannabinoids from hashish. J. Am. Chem. Soc. 1971, 93:217-224.
18. Gill E.W., Paton W.D., Pertwee R.G. Preliminary experiments on the chemistry and pharmacology of cannabis. Nature 1970, 228:134-136.
19. Grotenhermen F. Pharmacokinetics and pharmacodynamics of cannabinoids. Clin. Pharmacokinet. 2003, 42:327-360.
20. Guzman M., Sanchez C., Galve-Roperh I. Cannabinoids and cell fate. Pharmacol. Ther. 2002, 95:175-184.
21. Hatoum N.S., Davis W.M., Waters I.W., Elsohly M.A., Turner C.E. Synergism of cannabichromene and CNS depressants in mice. Gen. Pharmacol. 1981, 12:351-356.
22. Holley J., Hadley K., Turner C.E. Constituents of Cannabis sativa L. XI. Cannabidiol and cannabichromene in samples of known geographical origin. J. Pharm. Sci. 1975, 64:892-894.
23. Hunt C.A., Jones R.T. Tolerance and disposition of tetrahydrocannabinol in man. J. Pharmacol. Exp. Ther. 1980, 215:35-44.
24. Ilan A.B., Gevins A., Coleman M., ElSohly M.A., De Wit H. Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids. Behav. Pharmacol. 2005, 16:487-496.
25. Kanaan S.A., Safieh-Garabedian B., Haddad J.J., Atweh S.F., Abdelnoor A.M., Jabbur S.J., Saade N.E. Effects of various analgesic and anti-inflammatory drugs on endotoxin-induced hyperalgesia in rats and mice. Pharmacology 1997, 54:285-297.
26. Klein T.W. Cannabinoid-based drugs as anti-inflammatory therapeutics. Nat. Rev. Immunol. 2005, 5:400-411.
27. Liu J., Li H., Burstein S.H., Zurier R.B., Chen J.D. Activation and binding of peroxisome proliferator-activated receptor gamma by synthetic cannabinoid ajulemic acid. Mol. Pharmacol. 2003, 63:983-992.
28. Martin B.R., Compton D.R., Thomas B.F., Prescott W.R., Little P.J., Razdan R.K., Johnson M.R., Melvin L.S., Mechoulam R., Ward S.J. Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacol. Biochem. Behav. 1991, 40:471-478.
29. McPartland J.M., Russo E.B. Cannabis and cannabis extract: greater than the sum of the parts?. J. Cannabis Therapuetics 2001, 1:103-132.
30. Mechoulam R., Yagnitinsky B., Gaoni Y. Stereoelectronic factor in the chloranil dehydrogenation of cannabinoids. Total synthesis of dl-cannabichromene. J. Am. Chem. Soc. 1968, 90:2418-2420.
31. Mechoulam R., Peters M., Murillo-Rodriguez E., O'Hanuscaron L. Cannabidiol-recent advances. Chem. Biodivers. 2007, 8:1678-1692.
32. Mehmedic, Z., Chandra, S., Slade, D., Denham, H., Foster, S., Patel, A.S., Ross, S.A., Khan, I.A., Elsohly, M.A., 2010. Potency trends of delta(9)-THC and other cannabinoids in confiscated cannabis preparations from 1993 to 2008. J. Forensic Sci. May 4. [Epub ahead of print] PMID: 20487147.
33. Naidu P.S., Kinsey S.G., Guo T.L., Cravatt B.F., Lichtman A.H. Hierarchical regulation of inflammatory pain by inhibition of fatty acid amide hydrolase (FAAH). J. Pharmacol. Exp. Ther. 2010, 334:182-190.
34. O'Neil J.D., Dalton W.S., Forney R.B. The effect of cannabichromene on mean blood pressure, heart rate, and respiration rate responses to tetrahydrocannabinol in the anesthetized rat. Toxicol. Appl. Pharmacol. 1979, 49:265-270.
35. Pertwee R.G. The ring test: a quantitative method for assessing the " cataleptic" effect of cannabis in mice. Br. J. Pharmacol. 1972, 46:753-763.
36. Puffenbarger R.A., Boothe A.C., Cabral G.A. Cannabinoids inhibit LPS-inducible cytokine mRNA expression in rat microglial cells. Glia 2000, 29:58-69.
37. Rinaldi-Carmona M., Barth F., Heaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Neliat G., Caput D., Ferrara P., Soubrie P., Breliere J.C., Le Fur G. SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett. 1994, 350:240-244.
38. Smith P.B., Compton D.R., Welch S.P., Razdan R.K., Mechoulam R., Martin B.R. The pharmacological activity of anandamide, a putative endogenous cannabinoid, in mice. J. Pharmacol. Exp. Ther. 1994, 270:219-227.
39. Tallarida R.J., Porreca F., Cowan A. Statistical analysis of drug-drug and site-site interactions with isobolograms. Life Sci. 1989, 45:947-961.
40. Tallarida R.J. Drug synergism: its detection and applications. J. Pharmacol. Exp. Ther. 2001, 298:865-872.
41. Tallarida R.J. An overview of drug combination analysis with isobolograms. J. Pharmacol. Exp. Ther. 2006, 319:1-7.
42. Turner C.E., ElSohly M.A., Boeren E.G. Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J. Nat. Prod. 1980, 43:169-234.
43. Turner C.E., ElSohly M.A. Biological activity of cannabichromene, its homologs and isomers. J. Clin. Pharmacol. 1981, 21:283S-291S.
44. Varvel S.A., Bridgen D.T., Tao Q., Thomas B.F., Martin B.R., Lichtman A.H. Δ9-Tetrahydrocannbinol accounts for the antinociceptive, hypothermic, and cataleptic effects of marijuana in mice. J. Pharmacol. Exp. Ther. 2005, 314:329-337.
45. 1-tetrahydrocannabinol to blood cells and plasma proteins in man. J. Pharm. Pharmacol. 1974, 26:914-916.
46. Wiley J.L., Compton D.R., Dai D., Lainton J.A.H., Phillips M., Huffman J.W., Martin B.R. Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J. Pharmacol. Exp. Ther. 1998, 3:995-1004.
47. Wiley J.L., Martin B.R. Cannabinoid pharmacological properties common to other centrally acting drugs. Eur. J. Pharmacol. 2003, 471:185-193.
48. Wirth P.W., Sue Watson E., ElSohly M., Turner C.E., Murphy J.C. Anti-inflammatory properties of cannabichromene. Life Sci. 1980, 26:1991-1995.
49. Wirth P.W., Watson E.S., ElSohly M.A., Seidel R., Murphy J.C., Turner C.E. Anti-inflammatory activity of cannabichromene homologs. J. Pharm. Sci. 1980, 69:1359-1360.
50. Zurier R.B. Prospects for cannabinoids as anti-inflammatory agents. J. Cell Biochem. 2003, 88:462-466.