Friday, April 26, 2019

Understanding the Science of Cannabis: Terpenoids

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Terpenoids are a diverse class of chemical compounds naturally produced by a large variety of plants and flowers, including cannabis. These compounds are responsible for producing the various aromas these plants produce, and they also possess medically significant characteristics.

The fragrant imprint of each plant is a result of different combinations of terpenes. Cannabis is unique in that each strain has a unique profile of terpenes. Terpenes are believed to exhibit medicinal properties independent from the cannabinoids. Overall, terpenes contribute to a strain's particular influence - a phenomenon known as the entourage effect.

What has been surprising to scientists in recent years is that these terpenoids work synergistically with the cannabinoid compounds that cannabis produces to create a host of therapeutic effects. These terpenoids, in effect, enhance the effects of certain cannabinoid compounds like THC. They also help explain why cannabis provides a wide variety of psychoactive effects as well.

There are a multitude of terpenes that scientists have identified. One common example of a terpenoid would be Linalool, naturally produced in Lavender and in several strains of cannabis. Known for its anti-anxiety, anti-depressant, anti-bacterial, anti-inflammatory, and anti-convulsive attributes, its healing properties are enhanced when combined with CBD. Another common example would be Myrcene, a compound prevalent in mangoes and lemongrass and also produced in some cannabis strains, which has been known to have analgesic, anti-cancer, anti-inflammatory, and antispasmodic properties when combined with THC!


A chart detailing the three forms of cannabis: raw, heated, and aged



Linalool

Linalool is simple terpene alcohol, probably best known for the pleasant floral odor it gives to lavender plants. It is also known as β-linalool, licareol and linalyl alcohol. Linalool has been isolated in several hundred different plants including lavenders, citrus, laurels, birch, coriander and rosewood. Linalool has been used for several thousands of years as a sleep aid. Linalool is a critical precursor in the formation of Vitamin E. It has been used in the treatment of both psychosis and anxiety, and as an anti-epileptic agent. It also grants relief from pain and has been used as an analgesic. Its vapors have been shown to be an effective insecticide against fruit flies, fleas and cockroaches.




Anti-anxiety
Anti-bacterial
Anti-convulsive
Anti-depressant
Anti-insomnia


Terpinolene

Terpinolene is a monoterpene, part of the terpinene subfamily of terpenes. This family of four isomers is known for being anti-oxidant, immune-modulating and anti-biologically (anti-tumor, antibacterial, antifungal). It has also been used, for hundreds of years, in the treatment on insomnia. Terpinolene is found in oregano, marjoram, cumin, lilac, some citrus rind and conifers.




Anti-bacterial
Anti-fungal
Anti-insomnia
Anti-septic


Phytol

When the Chlorophyll molecule degrades, it breaks down into two parts. The ‘tail’ portion is Phytol, an oily diterpene. It is used in the synthesis of vitamins E and K and is known to have anti-oxidant properties.




Anti-insomnia


β-Myrcene 

β-Myrcene is a monoterpene, and for a wide variety of reasons, one of the most important terpenes. It is a precursor in the formation of other terpenes, as well. β-Myrcene is found fresh mango fruit, hops, bay leaves, eucalyptus, lemongrass and many other plants. β-Myrcene is known to be anti-tumor, anti-inflammatory, and used in the treatment of spasms. It is also used to treat insomnia, and pain. It also has some very special properties, including lowering the resistance across the blood to brain barrier, allowing itself and many other chemicals to cross the barrier easier and more quickly. In the case of cannabinoids, like THC, it allows it to take effect more quickly. More uniquely still, β-Myrcene has been shown to increase the maximum saturation level of the CB1 receptor, allowing for a greater maximum psychoactive effect. For most people, the consumption of a fresh mango, 45 minutes before inhaling cannabis, will result in a faster onset of psycho activity and greater intensity. β-Myrcene can be used in this same manner to improve uptake with a wide variety of chemical compounds.

Less well known is that fact that high β-Myrcene levels in cannabis (usually above 0.5%) result in the well known ‘couch lock’ effect of classic Indica strains of cannabis; Sativa strains normally contain less than 0.5% β-Myrcene.





Analgesic
Anti-cancer
Anti-inflammatory
Anti-insomnia
Anti-spasmotic


Citronellol

Citronellol is a monoterpenoid, closely related to Geraniol, and is found in geraniums, rose, some citrus rind. It has been used as a natural mosquito repellent for over 2,000 years, and to preserve fabric from moths. Like many other terpenoids, it is anti-biological, anti-inflammatory, immuno-regulating. As an anti-biological, it is well known for being aggressively anti-tumor. Also like many other terpenoids, it has a very low toxicity, having a high level of GRAS status and a high LD50 of 2650mg/kG of body weight.




Anti-cancer
Anti-inflammatory
Anti-insomnia
Anti-spasmotic


Caryphyllene Oxide

Caryophyllene oxide is the oxidation product of beta-Caryophyllene. It is well known for it’s anti-biological activity against fungus and tumors. It is also anti-oxidant. It may well play a roll in improving uptake of CBD/CBC in the CB2 receptor.




Anti-fungal
Anti-ischemic


α-Pinene

α-Pinene is one of the principle monoterpenes, and is important physiologically in both plants and animals, and to our environment. α-Pinene tends to react with other chemicals, forming a variety of other terpenes (like D-Limonene) and other compounds. α-Pinene has been used for centuries as a bronchodilator in the treatment of asthma; ever notice how your lungs seem to open up when hiking through a pine forest in the warm summer? α-Pinene is also anti-inflammatory. It’s found in conifer trees, orange peels among others, and known for it’s sharp sweet odor. α-Pinene is a major constituent in turpentine.




Anti-bacterial
Anti-fungal
Anti-inflammatory
Bronchodialator



Limonene

D-limonene is a cyclic terpene of major importance with a strong citrus odor and bitter taste. D-limonene was primarily used in medicine, food and perfume until a couple of decades ago, when it became better known as the main active ingredient in citrus cleaner. It has very low toxicity, and humans are rarely ever allergic to it. Medicinally, Limonene is best known for treating gastric reflux and as an anti-fungal agent. It’s ability to permeate proteins makes it ideal for treating toenail fungus. Limonene is also useful in treating depression and anxiety. Limonene also assists in the absorption of other terpenoids and chemicals through the skin, mucous membranes and digestive tract. It’s also been shown to be effective anti-tumor while at the same time being an immunostimulant. Limonene is one of two major compounds formed from α-Pinene.




Anti-anxiety
Anti-bacterial
Anti-cancer
Anti-depressant
Anti-fungal
Bronchodialator


β–Caryophyllene

Beta-caryophyllene is a sesquiterpene found in many plants including Thai basils, cloves and black pepper, and has a rich spicy odor. Research has shown that β–Caryophyllene has affinity for the CB2 endocannabinoid receptor. β–Caryophyllene is known to be anti-septic, anti-bacterial, antifungal, anti-tumor and anti-inflammatory.




Anti-bacterial
Anti-cancer
Anti-fungal
Anti-inflammatory
Anti-septic


Humulene

Humulene is a sesquiterpene also known as α-humulene and α–caryophyllene; an isomer of β–caryophyllene. Humulene is found in hops, cannabis sativa strains, and Vietnamese coriander, among others. Humulene gives beer its ‘hoppy’ aroma. It is anti-tumor, anti-bacterial, anti-inflammatory, and anorectic (suppresses appetite). It has commonly been blended with β–caryophyllene and used as a major remedy for inflammation, and is well known to Chinese medicine.




Anti-cancer
Anti-inflammatory
Anti-insomnia
Anti-spasmotic




The diverse palate of cannabis flavors is impressive enough, but arguably the most fascinating characteristic of terpenes is their ability to interact synergistically with other compounds in the plant, like cannabinoids. In the past few decades, most cannabis varieties have been bred to contain high levels of THC, and as a result, other cannabinoids like CBD have fallen to just trace amounts. This has led many to believe that terpenes play a key role in differentiating the effects of various cannabis strains.

Each individual terpene is associated with unique effects. Some promote relaxation and stress-relief, while others promote focus and acuity. Linalool, for example, is believed to be relaxing whereas limonene elevates mood.

The effect profile of any given terpene may change in the presence of other compounds in a phenomenon known as the entourage effect. More research is needed to understand each terpenes effect when used in harmony with others.

Their differences can be subtle, but terpenes can add great depth to the horticultural art and connoisseurship of cannabis. Most importantly, terpenes may offer additional medical value as they mediate our body’s interaction with therapeutic cannabinoids.

Many cannabis analysis labs now test terpene content, so you may have a better idea of what effects a strain might produce. With their unlimited combinations of synergistic effects, terpenes will certainly open up new scientific and medical terrains for cannabis research.

Leafly cannabis terpene wheel infographic


Sources: 
Project CBD 
Elemental Wellness Center
Steep Hill Labs
Leafly (images)


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