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There is a wealth of information available in the scientific literature regarding the classes of cannabinoid compounds and the receptors involved in the endocannabinoid system The endocannabinoid (EC) system helps the body manage anxiety, inflammation, and other physiological responses to different forms of stress.

A Chemist’s Perspective: Cannabinoids, Cannabis, and Caryophyllene

It has come to my attention that there has been a lot of confusion recently surrounding the properties of cannabinoid compounds found in certain oils. Individuals with ties to the CBD oil industry would have you believe that beta-caryophyllene, a compound found in Copaiba oil and Black Pepper oil, is not a cannabinoid. The same individuals would also have you believe that cannabidiol (CBD) oil never contains the psychoactive compound tetrahydrocannabinol (THC) or any of its isomers. This is not surprising, because both of these claims promote the CBD oil industry. Unfortunately, this misinformation has been perpetuated to the point that many people are convinced that it is accurate, despite strong evidence to the contrary.

I’ve prepared this article in hopes that I can set the facts straight. Having worked as a medicinal chemist for 15 years, I’ve learned a great deal about the chemical properties of all kinds of essential oils. I’ve even conducted my own chemical analyses of hemp, CBD, and cannabis oil in my lab at doTERRA. In this article, I will discuss the chemical properties of cannabinoid compounds found in the various cannabis oils and compare them with beta-caryophyllene. Beta-caryophyllene is the main compound found in Copaiba, doTERRA’s alternative to cannabis.

Beta-Caryophyllene is a Cannabinoid

There is a wealth of information available in the scientific literature regarding the classes of cannabinoid compounds and the receptors involved in the endocannabinoid system. For several years now, beta-caryophyllene has been known to be a cannabinoid. But don’t just take my word for it. Back in 2008, a study by J. Gertsch et al. rolled off the press with the unambiguous headline, “Beta-caryophyllene is a dietary cannabinoid.” 1 The study was published in Proceedings of the National Academy of Sciences of the United States of America, a prestigious scientific journal. Since then, at least a dozen more papers have been published on the subject, reemphasizing the fact that beta-caryophyllene is a cannabinoid. 2-13

By definition, a cannabinoid is any ligand, molecule, or class of molecules that acts on either or both of the currently identified cannabinoid receptors, CB1 and CB2. Interestingly, these two receptors produce significantly different physiological responses when activated. CB1 activation, caused by THC and other similar cannabinoids, results in a psychoactive drug high. On the other hand, CB2 activation by beta-caryophyllene (BCP) has produced results showing some promising benefits. These include supporting a healthy inflammatory response, soothing discomfort, and positively affecting mood without the psychoactive side effects associated with other cannabinoids. 2-4,10 It is true that the positive benefits associated with BCP have also been observed using other cannabinoids, such as THC, cannabidiol, and cannabinol, but using these compounds can also come with unwanted psychological effects, especially in the case of THC.

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Types of Cannabinoids

There are three distinct classes of cannabinoids: endocannabinoids, phytocannabinoids, and synthetic cannabinoids. Synthetic cannabinoids are found in certain pharmaceutical products designed to help with glaucoma, appetite stimulation, antiemetics, and other disease-linked targets. Endocannabinoids, on the other hand, are produced naturally by the body. These molecules are mainly composed of amines and amides. Endocannabinoids are pharmacologically similar to some phytocannabinoids, but vary greatly in their chemical structure. This gives different endocannabinoids the ability to produce different neurological responses, even when administered in similar doses. The primary function of endocannabinoids is to modulate normal physiological functions.

The last class of cannabinoids is known as the phytocannabinoids. These are molecules that are produced by plants such as Cannabis and Copaifera. The Cannabis species produces the commonly known molecules THC and CBD, while the Copaifera plant family produces only BCP. Although BCP differs significantly from other cannabinoids in its structure, it nonetheless reacts selectively with the CB2 receptor, thus defining it as a cannabinoid. 2 However, it is chemically distinct from other cannabinoids, which is why it cannot cause a positive result on a drug test. BCP is classified as a sesquiterpene based on its chemical structure and makeup. Research on BCP is ongoing and will continue to add to our understanding of its potential value.

Cannabidiol (CBD) oil can contain the psychoactive tetrahydrocannabinol (THC)

To be legally marketable, CBD oil is not supposed to contain any discernable amount of THC. 14 However, our own internal investigation involving analytical testing and evaluation has found that various CBD oils on the market do contain significant levels of THC and therefore could very likely trigger a psychoactive response and/or positive drug test. Our evaluation has also shown that commonly purchased brands of CBD oil can vary greatly in their claimed CBD content. In fact, in some samples we were not able to identify the presence of any CBD at all. In contrast, my analyses have shown that doTERRA oils are 100% free of THC, and oil compositions are consistent between batches.

Conclusion

In summary, this article is not intended to be a complete picture of the benefits of beta-caryophyllene nor an outline of the properties of the endocannabinoid system. Rather, it is a statement of scientifically-accepted facts aimed to clear up the misleading information on the molecules in question. My hopes are that reading this article will help individuals in their personal research on cannabinoids and, most importantly, their decisions about which oils to use in their daily life.

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Dr. Cody Beaumont, PhD
Director, Analytical Services & Quality Control

Endocannabinoids Explained

In this article, we review the endocannabinoid system and the effects of tetrahydrocannabinol (THC), Cannabidiol (CBD), and Beta-caryophyllene (BCP).

The endocannabinoid system

The endocannabinoid (EC) system helps the body manage anxiety, inflammation, and other physiological responses to different forms of stress. During strenuous exercise, stress, and other related stimuli, the body produces compounds called endocannabinoids. Endocannabinoids (ECs) are signaling molecules that trigger the activation of the EC system when they are detected by cannabinoid receptors.

Cannabinoid receptors (CRs) not only detect the presence of ECs, but they are also affected by molecules from outside sources that chemically resemble endocannabinoids. The term cannabinoid refers to any compound, produced by the body or from an outside source, that triggers the EC system by activating CRs. Anandamide is an EC compound produced in the body. Anandamide activates two types of CRs, cannabinoid receptor 1 (CB1) and cannabinoid receptor 2 (CB2).

A “runner’s high” is a perfect example of the EC system at work. After a long period of strenuous exercise, the body begins to produce anandamide in order to activate CRs and turn on the EC system. The “runner’s high” has two components: slight euphoria, and soothing of the discomfort in the muscles and joints. These two outcomes are linked with two distinct structures: the CB1 and CB2 receptors. CB1 receptors are mainly found in the brain and central nervous system, and are linked with pleasure and reward pathways. CB1 receptor activation leads to feelings of euphoria. CB2 receptors are found in the rest of the body, like the muscles, skin, and vital organs. They are mainly found on the surface of white blood cells, and their activation affects the regulation of inflammation chemicals called cytokines.

THC & CBD

THC is the main psychoactive compound in marijuana. According to GC/MS analyses conducted by doTERRA’s analytical chemists, it is found in high concentrations in many brands of cannabis oil, and it can also be found in hemp and CBD oil in more than just trace amounts. THC is known to activate both CB1 and CB2 receptors. It is generally accepted as a potent drug with powerful psychoactive properties.

CBD, another compound found in high quantities in marijuana, CBD oil, and hemp oil, does in fact interact directly with CB1 and CB2, but the interaction is so weak as to be negligible. 2 CBD actually exerts its effects on the EC system by a different mechanism than most cannabinoids.

Research shows that CBD acts on the enzyme FAAH, which breaks down anandamide. CBD actually slows down the enzyme’s activity, which leads to increased levels of anandamide in the body. 1 The reason why this is significant is because anandamide interacts with CB1 and CB2 receptors. Higher levels of anandamide would result in increased feelings of euphoria due to increased activation of CB1 receptors, as well as soothing of the tissues due to activation of CB2.

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CBD, by increasing levels of anandamide, has similar pharmacological effects as THC in that it affects the same two cannabinoid receptors, however the magnitude of the effect is much smaller compared with THC. CBD is generally considered non-hallucinogenic.

BCP

Soothing the tissues without triggering any sort of psychoactive response can be accomplished by using a compound with selective interaction with the CB2 receptor. Beta-caryophyllene (BCP) is a sesquiterpene compound found in hundreds of different plant species, and it has recently been recognized for its unique ability to interact with CB2 but not CB1 receptors. 3 Thus the alleged benefits of CBD or THC can be obtained without the psychoactive effects by using a product containing BCP. doTERRA’s new Copaiba essential oil has the highest BCP content of any oil, around 55% as confirmed by GC/MS analysis of doTERRA’s own Copaiba oil.

There is ample evidence pointing to the benefits of oral supplementation of beta-caryophyllene, but like CBD and hemp oil, further research in the form of human clinical trials is required. More promising are the low doses at which some of these studies have been conducted. These dosages suggest that as little as 1-2 drops of Copaiba oil or 3-4 drops of Black Pepper oil may provide noticeable results in humans. At this time, the systemic soothing properties of beta-caryophyllene have potential benefit as treatment for a wide range of health issues.* Still unexplored are the effects of CB2 receptor activation on human diseases for which there are few experimental models—such as learning disabilities and autism spectrum disorders—that many claim can benefit from using cannabis.

Conclusion

To summarize, there are many ways to modulate the body’s cannabinoid system. Products containing CBD, THC, and BCP all affect the endocannabinoid system. We acknowledge that health care professionals may recommend different products containing different kinds of cannabinoid compounds for different health issues. However, at doTERRA we believe that BCP-containing products are the most effective for healthy individuals seeking a product that they can use for self-care.

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

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