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Cannabinoids

Cannabidiol (CBD)

chemical structure of cannabidiol cannabinoid

Cannnabidiol (CBD) is the main cannabinoid constituent in industrial hemp flower (10-22+ % by weight).  This major cannabinoid, which is abundant in certain strains of industrial hemp, continues to receive significant attention from medical and research communities and appears to have tremendous medicinal potential and the ability to provide health and wellness benefits.  The following peer-reviewed references offer insight into the therapeutic potential of cannabidiol.

  • structure identified by Mechoulam and Shvo in 1963 (Mechoulam, R.; Shvo, Y. Tetrahedron 1963, 19, 2073-2078)

  • anticonvulsant (antiepileptic) in humans (Carlini, E. A.; Cunha, J. M. J. Clin. Pharmacol. 1981, 21, 417S-421-S)

  • CBD blocks delta9-THC provoked anxiety (Zuardi, A. W.; Shirakawa, I.; Finkelfarb, E.; Karniol, I. G. Psychopharmacolgy (Berl) 1982, 76, 245-250)

  • CBD improves psychosis (Zuardi, A. W.; Morais, S. L.; Guimaraes, F. S.; Mechoulam, R. J. Clin. Psychiatry 1995, 56, 485-486)

  • potent antioxidant, neuroprotective against glutamate neurotoxicity suggesting potential therapeutic for oxidative neurologic disorders such as cerebral ischemia (Hampson, A. J.; Grimaldi, M.; Axelrod, J.; Wink, D. Proc. Natl. Acad. Sci. USA 1998, 95, 8268-8273)

  • TRPV1 agonist, fatty acid amide hydrolase inhibitor, stimulates anandamide synthesis (Bisogno, T.; Hanus, L.; De Petrocellis, L.; Tchilibon, S.; Ponde, D. E.; Brandi, I.; Moriello, A. S.; Davis, J. B.; Mechoulam, R.; Di Marzo, V. Br. J. Pharmacol. 2001, 134, 845-852) 

  • CBD counteracts THC sedation (Nicholson, A. N.; Turner, C.; Stone, B. M.; Robson, P. J. J. Clin. Psychopharmacol. 2004, 24, 305-313)

  • enhances adenosine receptor A2A signaling by inhibition of adenosine transporter suggesting therapeutic role in inflammatory and chronic pain conditions (Carrier, E. J.; Auchampach, J. A.; Hillard, C. J. Proc. Natl. Acad. Sci USA 2006, 103, 7895-7900) 

  • anticonvulsant/antiepileptic (Jones, N. A.; Hill, A. J.; Smith, I.; Bevan, S.; Williams, C.; Whalley, B.; Stephens, G. J. Pharmacol. Exp. Ther. 2010, 332, 569-577)

  • CBD stimulates bone fracture healing via stimulation of lysyl hydroxylase activity (Kogan, N. M. et al. J. Bone Miner. Res. 2015, 30, 1905-1913)

  • CBD works as a negative allosteric modulator at CB1 receptors (Laprairie, R. B.; Bagher, A. M.; Kelly, M. E.; Denovan-Wright, E. M. Br. J. Pharmacol. 2015, 172, 4790-4805) 

Cannabidiolic Acid

chemical structure of cannabidiolic acid cannabinoid

Cannabidiolic acid (CBDa) is the predominant cannabinoid found in fresh (undried/uncured) hemp.  It is the precursor to CBD, which is formed through decarboxylation of CDBa during the curing process or when the plant material is combusted.  Recent studies on this phytocannabinoid are uncovering biological activity that may offer potential therapeutic benefits.

  • anti-inflammatory via selective COX-2 inhibition (Takeda, S.; Misawa, K.; Yamamoto, I.; Watanabe, K. Drug Met. Disp. 2008, 36, 1917-1921)  

  • Potent anti-emetic effects by enhancing 5-HT1A receptor activation (Bolognini, D.; Rock, E. M.; Cluny, N. L.; Cascio, M. G.; Limebeer, C. L.; Duncan, M.; Stott, C. G.; Javid, F. A.; Parker, L. A.; Pertwee, R. G. Br. J. Pharmacol. 2013, 168, 1456-1470)

  • inhibition of migration of highly invasive MDA-MB-231 human breast cancer cells (Takeda, S.; Himeno, T.; Kakizoe, K.; Okazaki, H.; Okada, T.; Watanabe, K.; Aramake, H. J. Nat. Med. 2017, 71, 286-291)



Cannabinol (CBN)

chemical structure of cannabinol cannabinoid

Cannabinol (CBN) is the stable oxidation product of delta-9 THC formed by prolonged exposure to air or UV light.  It was the first phytocannabinoid to be isolated and its structure was confirmed in the 1930s. 

  • Lewis lung adenocarcinoma tumor reduction in mice (Munson, A. E.; Harris, L. S.; Friedman, M. A.; Dewey, W. L.; Carchman, R. A. J. Natl. Cancer Inst. 1975, 55, 597-602)

  • potent antibacterial activity against MRSA (Appendino, G.; Gibbons, S.; Giana, A.; Pagani, A.; Grassi, G.; Stavri, M.; Smith, E.; Rahman, M. J. Nat. Prod. 2008, 71, 1427-1430)

  • increased appetite in rats (Farrimond, J. A.; Whalley, B. J.; Williams, C. M. Psychopharmacology (Berl) 2012, 223, 117-129)  

  • controversial claims over potent sedative effects (https://www.steephill.com/blogs/34/Cannabinol-(CBD):-A-Sleeping-Synergy) versus lack of psychoactivity

 

Cannabidivarin (CBDV)

chemical structure of cannabidivarin cannabinoid

Cannabidivarin (CBDV) is a homolog of CBD (sidechain shortened by 2 carbons) and is considered non-psychoactive.  However, it is in Phase II clinical trials for partial onset seizures.   

  • anti-convulsant activity in acute in vivo seizure models not mediated by CB1 receptor (Hill, T. D.; Cascio, M. G.; Romano, B.; Duncan, M.; Pertwee, R. G.; Williams, C. M.; Whalley, B. J.; Hill, A. J. Br. J. Pharmacol. 2013, 170, 679-692)

  • Phase II clinical trials initiated by GW Pharmaceuticals (http://globenewswire.com/news-release/2015/05/06/732705/10132893/en/GW-Pharmaceuticals-Initiates-Phase-2-Clinical-Study-of-Cannabidivarin-CBDV-in-Epilepsy.html)

  • therapeutic potential in reducing nausea (Rock, E. M.; Sticht, M. A.; Duncan, M.; Stott, C.; Parker, L. A. Br. J. Pharmacol. 2013, 170, 671-678)

 

Cannabichromene CBC)

chemical structure of cannabichromene cannabinoid

Cannabichromene (CBC) is a non-psychotropic phytocannabinoid found in significant levels in cannabis. 

  • inhibits endocannabinoid inactivation

  • TRPV1 agonist, fatty acid amide hydrolase inhibitor, stimulates anandamide synthesis (Bisogno, T.; Hanus, L.; De Petrocellis, L.; Tchilibon, S.; Ponde, D. E.; Brandi, I.; Moriello, A. S.; Davis, J. B.; Mechoulam, R.; Di Marzo, V. Br. J. Pharmacol. 2001, 134, 845-852)  

  • activates transient receptor potential ankyrin-1 (TRPA-1), thus reducing inflammation-induced hypermotility in vivo independent of CB1/CB2 and TRPA-1 receptors (Izzo, A.; Capasso, R.; Aviello, G.; Borreli, F.; Romano, B.; Piscitelli, F.; Gallo, R.; Capasso, F.; Orlando, P.; Di Marzo, V. Br. J. Pharmacol. 2012, 166, 1444-1460) 

Cannabigerol (CBG)

chemical structure of cannabichromene cannabinoid

Cannabigerol (CBG) is the decarboxylated version of cannabigerolic acid, the parent from which the other cannabinoids are derived  in the cannabis plant.  CBG is usually a minor component in the cannabinoid profile of cannabis samples.

  • antitumor activity against mouse skin melanoma cells in vitro (Baek, S.; Han, S.; Yook, C.; Kim, Y.; Kwak, J. Arch. Pharmacol. Res. 1996, 19, 228-230)

  • potent alpha 2-adrenceptor agonist (Cascio, M. G.; Gauson, L. A.; Stevenson, L. A.; Ross, R. A.; Pertwee, R. G. Br. J. Pharmacol. 2010, 159, 149-151)

  • inhibits colon cancer progression in vivo (Borrelli, F.; Pagano, E.; Romano, B.; Panzera, S.; Maiello, F.; Coppola, D.; De Petrocellis, L.; Buono, L.; Orlando, P.; Izzo, A. Carcinogenesis 2014, 35, 2787-2797)

Tetrahydrocannabinol (THC)

chemical structure of tetrahydrocannabinol

The primary psychoactive component of cannabis, delta 9-tetrahydrocannabinol (THC) was identified in 1964 by Gaoni and Mechoulam (J. Am. Chem. Soc. 1964, 86, 1646-1647).  It is the most well-known phytocannabinoid and is classified as a Schedule 1 substance by the DEA.  According to this classification, THC is a drug with no currently accepted medical use.  However, that status is changing as evidenced by the following potential therapeutic activity exhibited by this compound.  

 

  • potent anti-inflammatory activity (Evans, F. J. Planta Med. 1991, 57, 580-587)

  • potent antioxidant, neuroprotective against glutamate neurotoxicity suggesting potential therapeutic for oxidative neurologic disorders such as cerebral ischemia (Hampson, A. J.; Grimaldi, M.; Axelrod, J.; Wink, D. Proc. Natl. Acad. Sci. USA 1998, 95, 8268-8273)

  • competitive inhibitor of acetylcholinesterase and inhibitor of amyloid beta peptide aggregation suggesting potential therapeutic for Alzheimer’s Disease (Eubanks, L. M.; Rogers, C. J.; Beuscher, A. E.; Koob, G. F.; Olson, A. J.; Dickerson, T. J.; Janda, K. D. Mol. Phar. 2006, 3, 773-777)

  • partial agonist at CB1 and CB2 receptors (Pertwee, R. G. Br. J. Pharmacol. 2008, 153, 199-215)

  • effective pain management (Elikottil, J.; Gupta, P.; Gupta, K. J. Opiod Manag. 2009, 5, 341-357)

  • antiemetic activity (Parker, L. A.; Rock, E. M.; Limebeer, C. L. Br. J. Pharmacol. 2011, 163, 1411-1422)

  • antitumor activity against mouse skin melanoma cells in vitro (Baek, S.; Han, S.; Yook, C.; Kim, Y.; Kwak, J. Arch. Pharmacol. Res. 1996, 19, 228-230)

  • potent alpha 2-adrenceptor agonist (Cascio, M. G.; Gauson, L. A.; Stevenson, L. A.; Ross, R. A.; Pertwee, R. G. Br. J. Pharmacol. 2010, 159, 149-151)

  • inhibits colon cancer progression in vivo (Borrelli, F.; Pagano, E.; Romano, B.; Panzera, S.; Maiello, F.; Coppola, D.; De Petrocellis, L.; Buono, L.; Orlando, P.; Izzo, A. Carcinogenesis 2014, 35, 2787-2797)

Tetrahydrocannabinolic Acid (THCa)

chemical structure of tetrahydrocannabinolic acid

Tetrahydrocannabinolic acid is found in significant quantities of undried cannabis, but slowly converts to THC through a process called decarboxylation.  This process occurs to some degree during drying and curing and happens instantly when the cannabis is heated (smoked or vaped).  THCa is not a scheduled substance in the U.S.

  • conversion to THC in vivo is very limited (Moreno-Sanz, G. Cannabis Cannabinoid Res. 2016, 1, 124-130)

  • anti-inflammatory activity with potential for treatment of inflammatory bowel disease (IBD) via suppression of COX-2 gene expression (Nallathambi, R.; Mazuz, M.; Ion, A.; Selvaraj, G.; Weininger, S.; Fridlender, M.; Nasser, A.; Sagee, O.; Kumari, P.; Nemichenizer, D.; Mendelovitz, M.; Firstein, N.; Hanin, O.; Konikoff, F.; Kapulnik, Y.; Naftali, T.; Koltai, H. Cannabis Cannabinoid Res. 2017, 2, 167-182)

Tetrahydrocannabivarin (THCV)

chemical structure of tetrahydrocannabivarin

Tetrahydrocannabivarin (THCV) is found in cannabis samples from specific geographic locations (Turner, C. E.; Hadley, K.; Fetterman, P. J. Pharm. Sci. 1973, 62, 1739-1741) and differs from THC in the substitution of a propyl (3-carbon) side chain versus the pentyl (5-carbon) side chain found in THC.  It is not a specifically scheduled substance in the U. S.  

  • CB1 antagonist; CB2 partial agonist (Pertwee, R. G. Br. J. Pharmacol. 2007, 153, 199-215)

  • potential therapeutic for obesity-associated glucose intolerance in type 2 diabetes (Wargent, E. T.; Zaibi, M. S.; Silvestri, C.; Hislop, D.; Stocker, C. J.; Stott, C. G.; Guy, G. W.; Duncan, M.; Di Marzo, V.; Cawthornew, M. Nutrition and Diabetes 2013, 3, e68)

 FDA Disclaimer

**These statements have not been evaluated by the Food and Drug Administration. These products are not intended to diagnose, treat, cure, or prevent any disease.**

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