Growers Network Staff

September 6, 2017 7 min read
September 6, 2017
7 min read

Treatise on Decarboxylation – Part Two

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In this contributor article, Marco Troiani of Digamma Consulting discusses the chemistry of cannabinoid acids, and the chemical process behind smoking and decarboxylation of cannabis.

The following is an article produced by a contributing author. Growers Network does not endorse nor evaluate the claims of our contributors, nor do they influence our editorial process. We thank our contributors for their time and effort so we can continue our exclusive Growers Spotlight service.


The Decarboxylation of Cannabinoids


Decarboxylation of cannabinoids is crucial to understanding cannabis as medicine. Each cannabinoid acid decarboxylates into its corresponding free cannabinoid, such as THCA decarboxylating into THC and CBDA decarboxylating into CBD. Although the body is capable of converting cannabinoids into a variety of metabolites, once a cannabinoid acid enters the body it is generally not converted to its free cannabinoid form. This means that administering THCA and THC will have different effects on the human mind and body, and this essential difference can be found among all cannabinoids. Below is an overview of the major cannabinoids and the pharmacological and medical differences between their acids and their free forms.


THC / THCA


Tetrahydrocannabinol (THC) is a well-known cannabinoid that acts as the primary intoxicant and euphoriant of cannabis. THC is also one of the most practical and safe treatments for neuropathic, chronic, and other types of pain(1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12). THC is effective in addressing both the immunological and symptom component of Multiple Sclerosis (MS)(5, 6, 13, 14, 15, 16).

The chemistry of THCA's decarboxylation.

Despite the fact that THCA is not an intoxicant, it is a powerful medicine. THCA is one of the strongest anti-inflammatory agents in cannabis(7, 17, 18). Smokers receive very little to none of this cannabinoid, due to its decomposition in the smoking process. THCA is an anti-inflammatory agent, and according to one study, a more powerful neuroprotective agent than THC(19). THCA is a powerful COX-1 and COX-2 antagonist, similar to aspirin and ibuprofen, but with far less toxicity to the liver(17).

The effects of THCA and THC reflect the diversity of action on the human body a cannabinoid and its precursor acid can have. The other cannabinoids, CBD, CBG, CBC, and THCV all have acid forms which have distinct effects on human health.


CBD / CBDA


Cannabidiol (CBD) has been shown to be an effective medicine for people suffering from anxiety(5, 7, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28). CBD has also been shown to be effective at fighting breast cancer cells(29, 30). Many studies find that CBD promotes apoptosis, or cell suicide, in breast cancer cells while leaving the healthy cells unaffected.

The chemistry of CBDA's decarboxylation.

Cannabidiolic acid (CBDA) is CBD’s acid precursor from raw cannabis flower. CBDA has also been shown to fight human breast cancer, but in a different way. Whereas CBD causes apoptosis in breast cancer cells, CBDA has been shown to slow or stop metastasis of breast cancer cells by arresting their motility, or ability to move throughout the body(31). This evidence would indicate that a breast cancer patient may want to talk to their doctor about dual CBD/CBDA therapy, taking both decarboxylated CBD and raw CBDA together.


CBG / CBGA


Cannabigerol (CBG) has been shown to have some potent anti-inflammatory properties that are particularly applicable in inflammatory bowel disease (IBS)(32). Additionally, CBG has been shown to have some properties not known among many other cannabinoids, such as an ability to interact with human adrenal receptors and serotonin receptors(33). Currently, more studies need to be done on Cannabigerolic Acid (CBGA) in isolation from CBG to learn what, if any, differences there are between the cannabinoid and its precursor acid on human health.

The chemistry of CBGA's decarboxylation.


References


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  2. De Petrocellis, Luciano, et al. "Plant-derived cannabinoids modulate the activity of transient receptor potential channels of ankyrin type-1 and melastatin type-8." Journal of Pharmacology and Experimental Therapeutics 325.3 (2008): 1007-1015.
  3. Fine, Perry G., and Mark J. Rosenfeld. "The endocannabinoid system, cannabinoids, and pain." Rambam Maimonides medical journal 4.4 (2013).
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  5. Kogan, Natalya M., and Raphael Mechoulam. "Cannabinoids in health and disease." Dialogues in clinical neuroscience 9.4 (2007): 413.
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  10. Ware, Mark A., et al. "Smoked cannabis for chronic neuropathic pain: a randomized controlled trial." Canadian Medical Association Journal 182.14 (2010): E694-E701.
  11. Nurmikko, Turo J., et al. "Sativex successfully treats neuropathic pain characterised by allodynia: a randomised, double-blind, placebo-controlled clinical trial." Pain® 133.1 (2007): 210-220.
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  17. Ruhaak, Lucia Renee, et al. "Evaluation of the cyclooxygenase inhibiting effects of six major cannabinoids isolated from Cannabis sativa." Biological and Pharmaceutical Bulletin 34.5 (2011): 774-778.
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  19. Moldzio, Rudolf, et al. "Effects of cannabinoids Δ (9)-tetrahydrocannabinol, Δ (9)-tetrahydrocannabinolic acid and cannabidiol in MPP+ affected murine mesencephalic cultures." Phytomedicine 19.8 (2012): 819-824.
  20. Bergamaschi, Mateus M., et al. "Cannabidiol reduces the anxiety induced by simulated public speaking in treatment-naive social phobia patients." Neuropsychopharmacology 36.6 (2011): 1219-1226.
  21. Bergamaschi, Mateus Machado. Subjecffve effects of cannabidiol in anxiety disorder and canabinoid excretion in chronic daily cannabis smokers during sustained abstinence. Diss. Universidade de São Paulo.
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  23. Gururajan, Anand. "Comment on:“Anxiogenic-like effects of chronic cannabidiol administration in rats”(Elbatsh MM, Assareh N, Marsden CA, Kendall DA, Psychopharmacology 2012)." Psychopharmacology (2012): 1-2.
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  26. Sarris, Jerome, Erica McIntyre, and David A. Camfield. "Plant-based medicines for anxiety disorders, part 2: a review of clinical studies with supporting preclinical evidence." CNS drugs 27.4 (2013): 301-319.
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  29. Ligresti, Alessia, et al. "Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma." Journal of Pharmacology and Experimental Therapeutics 318.3 (2006): 1375-1387.
  30. Caffarel, María M., et al. "Cannabinoids: a new hope for breast cancer therapy?." Cancer treatment reviews 38.7 (2012): 911-918.
  31. Takeda, Shuso, et al. "Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration." Toxicology letters 214.3 (2012): 314-319.
  32. Borrelli, Francesca, et al. "Beneficial effect of the non-psychotropic plant cannabinoid cannabigerol on experimental inflammatory bowel disease." Biochemical pharmacology 85.9 (2013): 1306-1316.
  33. Cascio, M. G., et al. "Evidence that the plant cannabinoid cannabigerol is a highly potent α2‐adrenoceptor agonist and moderately potent 5HT1A receptor antagonist." British journal of pharmacology 159.1 (2010): 129-141.
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Want to get in touch with Marco? He can be reached via the following methods:

  1. Email: marco@digammaconsulting.com

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About the Author

Marco Troiani is one of the founding members of Digamma Consulting and the laboratory manager. He was also the laboratory manager of DB Labs from its founding 2015-2016. His responsibilities included developing detection methods for terpenes and solvents (GC-MS), metals (ICP-MS), pesticides (GC-MS-MS), and Total Yeast and Mold, Total Aerobic Bacteria, Total Coliform Bacteria, and Salmonella spp. in cannabis and associated products.