Tales of terpenes: caryophyllene

//Tales of terpenes: caryophyllene

Tales of terpenes: caryophyllene

Dr. Jokūbas Žiburkus, PhD and Ahmad Abdulla for CANNTELLIGENCE


Of Cannabis and Peppers

One of the dominant terpenes found in certain strains of cannabis is beta caryophyllene. We found that some terpene profiles posted by Analytical 360 laboratory for some strains exceeded 1% of caryophyllene. For example, HPLC analysis of ‘Candyland 1’ and ‘Industrial Plant CBD’ flower showed that they contain a whopping 1.6% of caryophyllene. Other recently tested strains with high caryophyllene content were: ‘Cookies’ (1.3%), ‘Medi Haze’ (1.1%), ‘Super Silver Haze’ (1.25% caryophyllene oxide), and ‘Cookies and Cream’ wax (1.7%).  There are undoubtedly many more strains and cultivars where beta-caryophyllene is the main or one of the dominant terpenes. It is also not uncommon that waxes and concentrates prepared using cold temperatures, contain higher percentages of cannabinoids and terpenes.

Beta caryophyllene is also found in several other plants, such as hops, cloves, and peppers (discussed in a recent article by Dr. Russo1). Hops and cannabis are the closest relatives, both members of the canabaceae family and the higher Rose order. Peppers, on the other hand, are not closely related to the canabaceae family. They are members of the Piperales order and the piperaceae family. Like cannabis, peppers are also flowering plants (angiosperms), but the main similarity between these two different plants lies in the expression of our featured sesquiterpene beta caryophyllene (BCP). BCP is arguably the most abundant, best studied terpene, with potentially the highest therapeutic potential.

Peppers, compared to cannabis, can contain much higher amounts of beta caryophyllene. While the common pepper (piper nigrum) contains a modest 7% BCP, the West African Ashanti pepper pod contains up to 60% of BCP2. BCP gives peppers the spicy and bitter taste. Some, raw hemp or high THC cannabis extracts that contain high levels of BCP will have a bitter and spicy taste and smell.

Beta caryophyllene is the FDA approved food additive, also regarded as GRAS (generally regarded as safe). That means that BCP can be added to any food or beverage. Because BCP has many reported medicinal properties, one should take a note of BCP in their diets or in their cannabis products.


How does beta caryophyllene work?

It turns out that beta caryophyllene is not only found in cannabis and peppers, but that it actually interacts with our body’s endogenous cannabinoid system. The ECS in our bodies consists of endogenously synthesized endocannabinoid molecules (anandamide and 2-AG), their synthesizing and degrading enzymes, and cannabinoid receptors 1 and 2 (CB1 and CB2). CB1 receptors found in high densities in the brain are intoxicating and promote hunger. CB2 receptors have lower expression levels in the brain than CB1. CB2 receptors instead are found in the peripheral body organs, like the spleen, pancreas, and the immune system cells. BCP is one of the most selective natural agents of the CB2 receptors3.


BCP is a cannabimimetic compound. It activates CB2 receptors and is involved in the regulation of the inflammatory processes and the immune system function. BCP has been shown to have analgesic and anti-inflammatory properties in mouse models of pain. CB2 activation by BCP, exerts anti-anxiety properties, and appears to have protective effects in the digestive system as well. A recent review in Cancer Medicine, highlights BCP’s anti-cancer properties and the ability to enhance some chemotherapy treatments4. Several authors suggest that because multiple activities of BCP are analgesic and anti-inflammatory, and contain anti-cancerous properties, this molecule may become ‘particularly valuable in oncology’.

Another important chemical in pepper that most of us are familiar with is capsaicin.  Interestingly, capsaicin also has analgesic properties, because it alleviates pain by binding to another protein receptor called TRPV (transient receptor potential vanilloid) receptors5. Thus, peppers have BCP and capsaicin, packing a spicy, hot, anti-inflammatory punch. The same goes for cannabis, whereby major cannabinoids like THC and CBD target TRPV channels as well and contain anti-inflammatory properties (in part mediated by BCP). In sum, the flowering cousins like peppers and cannabis seem to share some of the same biological targets and may exert synergies with other components of the cannabis plant.

The cannabis and healthcare communities’ knowledge regarding terpenes and the entourage effect are increasingly gaining traction and influencing scientific and clinical applications. In order to collectively advance the safe and effective use of cannabis, much more cross-talk is needed between the growers, product developers, dispensary owners, consumers, and healthcare professionals. Indeed, healthcare professionals recommending medical cannabis must be aware that THC and CBD are not the only important components of the cannabis plant. Thus, understanding the distinct components of cannabis and its beneficial synergies and/or potential harm, is the key to unlocking the most effective individualized cannabis therapies.



BCP – Beta-caryophyllene



Aroma: cloves, spices, pepper, turpentine

Found in: cloves, hops, rosemary, peppers, cannabis

Caryophyllene variants. There are many variations of caryophyllene, including but not limited to beta caryophyllene oxide (BCPO), tans-caryophyllene, L-caryophyllene. BCPO also has anti-cancer and analgesic properties.




 Formula  C15H24  C21H30O2  C22H30O4  C21H30O2  




Weight (g/mol)












Boiling point (ºC)


 129-130  1576  >1457*  160-1806  >1457*

*Decarboxylation temperature. Boiling points obtained from Pubchem.gov

Factoid: Because BCP is widely abundant in cannabis, it is the terpene that drug dogs are trained to smell when identifying cannabis.

More Brainy Science: In addition to activating CB2, BCP also activates peroxisome proliferated activator receptors (PPARs), which affects cellular development, gene transcription, and formation of tumors.

Canntelligence ©    www.canntelligence.com 


  1. Russo EB. Beyond Cannabis: Plants and the Endocannabinoid System. Trends Pharmacol Sci 2016;37(7):594-605.
  2. Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M. Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry. Journal of chromatography A 2002;976(1-2):265-275.
  3. Gertsch J, Pertwee RG, Di Marzo V. Phytocannabinoids beyond the Cannabis plant – do they exist? Br J Pharmacol 2010;160(3):523-529.
  4. Fidyt K, Fiedorowicz A, Strzadala L, Szumny A. beta-caryophyllene and beta-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer medicine 2016;5(10):3007-3017.
  5. Jordt S-E, McKemy DD, Julius D. Lessons from peppers and peppermint: the molecular logic of thermosensation. Current Opinion in Neurobiology 2003;13(4):487-492.
  6. McPartland JM, Russo EB. Cannabis and Cannabis Extracts. Journal of Cannabis Therapeutics 2001;1(3-4):103-132.
  7. Veress T, Szanto JI, Leisztner L. Determination of cannabinoid acids by high-performance liquid chromatography of their neutral derivatives formed by thermal decarboxylation. Journal of Chromatography A 1990;520:339-347.


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By | 2017-04-21T20:22:53+00:00 April 19th, 2017|Categories: Uncategorized|0 Comments

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