Cannabinoids are produced via biosynthesis. This is the process in which enzymes cause a series of chemical reactions that create complex molecules out of simple ones7.
Other common cannabinoids include:2
- Delta 8-tetrahydrocannabinol (∆8-THC)
- Cannabigerol (CBG)
- Cannabinol (CBN)
- Cannabichromene (CBC)
- Cannabivarin (CBV)
- Cannabidivarin (CBDV)
- Delta 9-tetrahydrocannabivarin (THCV)
- Delta-9 Tetrahydrocannabiphorol (∆9-THCP)
- Cannabidiphorol (CBDP)
- Cannabimovone (CBM)
Cannabinoids v.s. Phytocannabinoids
While you may see these terms used interchangeable, they do have technical differences3.
Cannabinoid is a broad term for compounds produced by plants and mammals alike. These compounds help balance and regulate a variety of biological functions.
“Endogenous cannabinoids, or endocannabinoids, are cannabinoids produced inside the mammalian body. Every function in our bodies requires a specific balance of factors in order to perform at maximum capacity. When this balance is achieved, it’s called homeostasis. Endocannabinoids play a major role in survival by helping the body maintain homeostasis. Because our bodies already use cannabinoid molecules to regulate many functions, we’re inherently endowed with many targets the cannabis plant can activate.”3
Despite these technical differences, phytocannabinoids and endocannabinoids aren’t structurally different from each other3. They both activate the endocannabinoid system, but it appears endocannabinoids have a homeostatic effect, whereas phytocannabinoids produce medicinal effects.
However, unlike endocannabinoids, phytocannabinoids “cannot be degraded by our body”20. Instead, biotransformation occurs in the liver to trigger a series of chemical events (hydroxylation and oxidation) until phytocannabinoids are broken down into a water-soluble compound (glucuronide) that can be easily excreted.
Lastly, phytocannabinoids aren’t exclusive to cannabis — they’re found in other plant species, as well8. Phytocannabinoids found in other plants also interact with the endocannabinoid system.
However, endocannabinoids and phytocannabinoids target receptors outside the endocannabinoid system, as well4.
Endocannabinoid-like mediators are mediators that share the same chemical class as endocannabinoids (amides or esters of long-chain fatty acids), and the same degrading pathways as well as enzymes4.
Endocannabinoid-like mediators differ from anandamide and 2-AG, as their preferred protein receptors aren’t CB1 and CB2. Rather, it’s thought endocannabinoid-like mediators indirectly influence endocannabinoid levels or their actions4. “The endocannabinoid-like compounds do not bind to CB1 nor to CB2, but inhibit endocannabinoid degradation thus prolonging their biological activity with an ‘entourage effect.’”20
The Entourage Effect
The entourage effect is a popular (and widely accepted) theory that all of these compounds — namely phytocannabinoids and terpenes — work together to produce unique effects21. This would explain why the effects of cannabis products can vary greatly, even within the same strain or from the same plant21,20
Cannabinoid Acids (Raw Cannabinoids — THCa, CBDa, CBGa)
The “acid” form of phytocannabinoids (THCa, CBDa, CBGa, etc…) are the “pre-cannabinoids” produced by the cannabis plant’s cannabinoid biosynthetic pathways22,23. These compounds become THC, CBD, and CBG through oxidation (aging) and decarboxylation (heating) due to the oxidative instability of alkylic cannabinoids22.
In other words, cannabinoid acids (for example, THCa) are raw cannabinoids, whereas the non-acid forms are the aged and heated cannabinoids. THCa and CBDa are sometimes isolated in concentrated forms to create “Crystalline THC or CBD,” the “purest form of [cannabis] concentrate available”24. Additionally, THCa and CBDa have demonstrated similar anti-nausea, anti-inflammatory, and anti-tumor properties as their heated and aged forms, THC and CBD43.
CBGa is unique in that it is found in high concentrations in the cannabis plant during its developmental stages2,23. As the plant matures, CBGA is converted into THCa and CBDa. Any CBGa that remains will become CBG through decarboxylation23.
“Synthetic cannabinoids are not one drug. Hundreds of different synthetic cannabinoid chemicals are manufactured and sold. New ones with unknown health risks become available each year. Synthetic cannabinoids are popular because users often believe they are legal and relatively safe.”17
By design, synthetic cannabinoids are created to mimic THC and other phytocannabinoids17,18. Initially, they were created to help researchers further explore the endocannabinoid system, but have quickly spread to the point of being abused worldwide18.
“K2,” “Spice,” and “Kronic” are a few examples of “brand name” synthetic cannabinoids, according to the CDC17.
Contrary to popular misconceptions, many synthetic cannabinoids are illegal. They can also cause a variety of negative side effects, including:
- Agitation and irritability
- Confusion and concentration difficulties
- Delusions, hallucinations
- Difficulty breathing
- Gastrointestinal distress
- Heart attack
- Kidney failure
- Muscle damage
- Sleepiness and dizziness
Synthetic cannabinoids may also be addictive, which can lead to severe withdrawal symptoms upon abruptly ceasing use of them.
Over 100 unique phytocannabinoids have been identified in cannabis plants, with tetrahydrocannabinol (THC or ∆9-THC) and cannabidiol (CBD) being the most prominent and well-researched compounds1,2. Other common phytocannabinoids include Delta 8-THC, CBG, CBN, CBC, CBV, CBDV, and THCV.
While the terms “cannabinoids” and “phytocannabinoids” are often used interchangeably, there are technical terms between them. Cannabinoid is a broad term for compounds produced by plants and mammals alike. These compounds help balance and regulate a variety of biological functions. Phytocannabinoids are produced by plants, whereas endocannabinoids are produced endogenously (internally, naturally) by mammals3,8.
In other words, all phytocannabinoids and endocannabinoids are cannabinoids, but not all cannabinoids are endocannabinoids or phytocannabinoids (they’re either one or the other).
Therapeutic benefits have been identified for all phytocannabinoids, with some producing pain-relieving effects, inhibiting inflammation, reducing anxiety, improving sleep, and decreasing nausea. Some phytocannabinoids also have neuroprotective, anticonvulsant, and antioxidant properties2. Likewise, some cannabinoids are psychoactive while others (namely, derivatives of CBD) are non-psychoactive.
Considering that over 100 unique phytocannabinoids have been identified in cannabis plants, it’s interesting to ponder how research on cannabinoids will progress in the years to come1,2. Perhaps the list of common cannabinoids will grow to include even more compounds.
However, there’s still plenty to learn about the cannabinoids we’ve already focused on over the last few decades.
For example, CBD products represent a $1.6 billion industry in the United States97, but its role in the endocannabinoid system remains elusive2,7. Additionally, very little research has been done on the exact pharmacology of CBV2,35.
Continuing to expand our understanding of cannabinoids is critical to appreciating the entourage effect, which will enhance our ability to recommend specific strains for achieving specific medicinal benefits.
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