What Are Terpenoids, And Why Are They Crucial to the Effects of Cannabis?

You may be surprised to learn that cannabis has over four hundred chemical compounds! While cannabinoids have traditionally received the most attention, the role terpenoids play in the healing process has been growing in importance in recent years.

Terpenoids exist throughout the plant world and also play an essential role in your cannabis experience. Recent studies suggest that terpenoids can assist or inhibit the effects of cannabinoids and are responsible for cannabis plants' aroma.

As far back as 2001, Dr. John MacPartland and Dr. Ethan Russo began presenting early evidence that terpenes enhance the effects of cannabinoids (The Entourage Effect). Later in 2011, Dr. Ethan Russo gave a deeper dive into understanding the synergistic interaction between cannabinoids and terpenes. We've gathered everything you need to know about terpenoids in this article to get you up to speed.

What are Terpenoids and Terpenes?

Terpenes and terpenoids provide the essential oils of many types of medicinal plants and flowers. Both terms are used interchangeably and reference the beautiful bevy of aroma that makes each cannabis cultivar uniquely beneficial. However, it's more accurate to say that the interaction or combination between the flavonoids and the terpenes contributes to the unique fragrance and taste of marijuana.

Terpenes

A comprehensive terpene wheel has over 20,000 terpene types; yet, Cannabis has more than two hundred terpenes identified, and only a few have been studied. Most terpenes are found in plants and are made up of isoprene molecules, each containing five carbon atoms.

Monoterpenes - 2 Isoprene Units

Sesquiterpenes - 3 Isoprene Units

Diterpenes - 4 Isoprene Units

Sesterterpenes - 5 Isoprene Units

Monoterpenes are the simplest form, containing two isoprene molecules, sesquiterpenes have three isoprene molecules, and diterpenes have four, and so on.

Terpenoids

Terpenoids are terpenes that have undergone oxidation through drying and curing. Terpenoids and cannabinoids can be found in trichomes' resin covering the flowers' exterior and small leaves.

The main difference between these two terms (terpenes and terpenoids) is that terpenes are organic hydrocarbons; whereas, terpenoids have additional atoms and have undergone oxidation (cured and dried) or been chemically modified. In simple terms, terpenes can be seen as "wet" and terpenoids as "dried out."

Human Senses and Terpenoids

The human sense of smell can trigger memories and emotions. Terpenes are "fat-loving" compounds that readily cross the blood-brain barrier and are the foundation behind essential oils and aromatherapy. That's why cannabis aroma is no different; its therapeutic properties can soothe body and mind functions.

Monoterpenes include α- and β-pinene, d-limonene, β-myrcene, terpinolene, and linalool. β-caryophyllene and α-humulene are Sesquiterpenes commonly found in no small degree in Cannabis extracts.

Here are some common terpenes found in Cannabis and their therapeutic benefits:

α-Pinene: this very common monoterpene can also be found in pine needles, rosemary, and basil. It acts as an anti-inflammatory, a bronchodilator, and an acetylcholinesterase inhibitor, which may aid in memory functions. This last feature is believed to counteract short-term memory loss induced by THC intoxication.

Pinene holds excellent potential for COPD and Alzheimer's Disease and has been used as an anti-cancer agent in Chinese medicine.

D-limonene: commonly found in lemons and citrus, is absorbed quickly into the bloodstream and can improve other terpenes' absorption. Limonene stimulates the immune system, has anti-anxiety properties, and has been shown to have potent antibacterial and antifungal benefits. It is also believed to potentially help in the suppression of breast cancer cells.

β-myrcene is described as earthy or herbal. It is commonly found in hops, bay leaves, and lemongrass, among others. Myrcene is recognized as a potent anti-inflammatory, a pain reliever, muscle relaxant, and sedative. In the case of cannabinoids, myrcene can increase the speed of action and effects are felt faster.

Terpinolene: about one in ten strains is dominant in terpinolene. It is found in nutmeg, lilacs, and cumin. It may be the least common cannabis terpene and is usually only found in small amounts. Apart from its fresh scent, it possesses antibacterial and antifungal properties, and research suggests it may act as an insect repellent, keeping pests like mosquitoes at bay.

D-Linalool, commonly found in lavender, is an analgesic (pain reliever), has anti-anxiety properties, is an anti-inflammatory, reduces seizures, and is a local anesthetic. It is also believed to improve immunity and has been used in the treatment of lung inflammation.

β-caryophyllene, a well-known active principle of black pepper, is a potent anti-inflammatory and can protect against gastric issues. Since it binds to the CB2 receptor, it is sometimes considered to be a phytocannabinoid.

Humulene is a sesquiterpene. It is also found in Hops and cannabis Sativa strains. Humulene is believed to be an active mechanism in fighting tumors and has also been shown to exhibit antibacterial properties against Staphylococcus Aureus. Also, it has been used to facilitate weight loss by its appetite suppressing benefits.

Nerolidol is also a sesquiterpene with sedative properties with a floral or woody aroma. It is believed to be an effective agent to fight malaria and ulcers, and an anti-cancer agent for its ability to disrupt the membrane of cancer cells. Its potential applications include prevention and treatment of infections, fortification of existing sanitizing procedures, and enhancement of food safety.

Valencene: a sesquiterpene that can offer anti-inflammatory, anti-allergic, and skin protectant benefits. A recent study showed that valencene could boost the efficacy of the chemotherapy drug, Doxorubicin.

Ocimene is a monoterpene with a beautiful citrus, sweet, earthy aroma. It can be found in parsley, orchids, and mint. Ocimene can potentially suppress the production of different inflammatory substances emitted by the immune system and may help treat diabetes symptoms by inhibiting key enzymes' proliferation.

Bisabolol is known for its floral, fresh, and sweet aroma apart from its calming effects. It has widely been used in the cosmetic industry and can be commonly found in chamomile. It has been reported that bisabolol has anti-irritant, antioxidant, analgesic, antimicrobial, and anti-inflammatory benefits.

Fenchol is also a monoterpene known for its earthy and refreshing aroma. It has shown potential benefits as an antimicrobial, antibacterial, and antioxidant agent.

Farnesene is commonly characterized by its green apple aroma. It can be found in turmeric and has anti-inflammatory properties and tumor-inhibiting traits that can help treat colon and pancreatic cancers. Farnesene calming effects are also believed to help suppress spasms.

Caryophyllene Oxide is characterized by its peppery, spicy profile found in edible plants like cloves, cinnamon, or black pepper. Due to its affinity to the peripheral CB2 receptors, caryophyllene oxide is often present in anti-inflammatory salves and topical. Its potential medicinal benefits are related to alcohol craving reduction, anti-cancer, anti-anxiety, anti-inflammatory, analgesic, and antidepressant.

A-phellandrene is a monoterpene with a woody, minty, and mildly citrus aroma. It is commonly used in perfumes and a component of Eastern therapies due to its easy absorption. Alpha-phellandrene has several medical benefits, patients trying to manage pain or fighting cancer can benefit from its analgesic and anti-tumor effects. It is considered an anti-cancer and is shown to decrease human liver tumor cells' viability, a fungicide, an anti-inflammatory, and analgesic.

Final Hit: There is still a lot of terpenes science to discover.

Continuously discovering new therapeutic treatments is of tremendous importance to meet current and future public health challenges. Terpenes and terpenoids are an essential component of cannabinoid therapy.

Nature holds great potential in providing us with safer, gentler herbal remedies. As Cannabis laws continue to evolve, research on Cannabis and its therapeutic uses will continue to grow, expanding our ability to treat various conditions with fewer adverse side effects.

Produced in partnership MMJ Knowledge

This information is not intended as medical advice, it is for educational purposes only. As always with medical conditions and symptoms, please consult with your doctor for personalized medical advice.  The statements made regarding these products have not been evaluated by the Food and Drug Administration. The efficacy of these products has not been confirmed by FDA-approved research. These products are not intended to diagnose, treat, cure, or prevent any disease.

References:

Izzo AA, Borrelli F, Capasso R, Di marzo V, Mechoulam R. Non-psychotropic plant cannabinoids: new therapeutic opportunities from an ancient herb. Trends Pharmacol Sci. 2009;30(10):515-27. PDF

Mechoulam R. Plant cannabinoids: a neglected pharmacological treasure trove. Br J Pharmacol. 2005;146(7):913-5. PDF

Russo EB. Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br J Pharmacol. 2011;163(7):1344-64. PDF

Terpenes and Terpenoids: The Ultimate Guide.