Your Guide to Terpenes in Cannabis

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von Jennifer McFarlane

The study of terpenes in cannabis is seriously taking off! But what exactly are terpenes, and what do you need to know?

Terpenes are among the most important organic compounds present on this earth, and their uses are incredibly diverse. Almost all plants produce terpenes or terpenoids in some form or another – and cannabis produces plenty!

While terpenes have many biological functions, one of the most instantly recognizable is their ability to express intense aromas and flavors. They are fundamental to the floral, fruity and spicy fragrances in plants and flowers. The aromatic terpenes in cannabis can be extremely pungent, making it a recognizable plant indeed. It’s no wonder that strains of cannabis have names like Skunk, Cheese, Grapefruit and so on.

What Are Terpenes – The Basics

Furthermore, cannabis is very creative when it comes to combining these terpenes to create new aromas. Many flowering plants, such as roses, smell generally similar – but cannabis has the ability to produce an incredible diversity of fragrances, from fruity and flowery through to spicy, earthy and even chemical. All of these unique and diverse aromas are primarily made up of different combinations of these fascinating molecules – the terpenes.

Terpenes are an extremely large class of organic compounds. When added together with the terpenoids, which are very similar to terpenes and fulfil many similar biological functions, they are the single largest class of naturallyoccurring molecule!

Terpenes and terpenoids are also quite similar to cannabinoids. In fact, cannabinoids are sometimes referred to as “terpenophenolic” compounds. What’s more, there’s a specific part of the cannabis plant that’s responsible for creating both cannabinoids and terpenes – the trichomes. Generally, plants that produce abundant, resin-filled trichomes should be high in both cannabinoids and terpenes.

Terpenes have a basic molecular structure, which is always a multiple of a basic molecular “building block” that is ubiquitous in the plant kingdom. This “building block” is isoprene, which has the structure C5H8 – five carbon atoms and eight hydrogen atoms per molecule.

Monoterpenes, Sesquiterpenes – What Do These Terms Mean?

There are various “groups” of terpenes, which are organized according to how many isoprene units they contain. Isoprene itself is often considered a “hemiterpene” – basically “half a terpene”. When you put two isoprene units together, you get the first group of “true” terpenes.

These are the monoterpenes, and they all have the molecular formula C10H16. There are many different monoterpenes with different aromas, flavors and properties – the only thing that distinguishes them is that their atoms arrange themselves in subtly different ways! Next, there are other groups of terpenes that contain a greater number of isoprene units. Sesquiterpenes are the next group – they have three isoprene units, and the formula C15H24.

There are also diterpenes, sesterterpenes, triterpenes, and so on, all with increasing multiples of isoprene units. But as monoterpenes and sesquiterpenes are by far the most abundant types of terpenes in cannabis, that’s what we’ll focus on in this article.

So What About Terpenoids? How Do They Fit In?

Of course, we can’t go forward without quickly bringing you up to date on what terpenoids are. While terpenes themselves are simple hydrocarbons, terpenoids may contain oxygen, phosphorus or various other atoms within their molecules.

However, they are still based on the same concept of repeating isoprene units – and just like we have monoterpenes, sesquiterpenes and so on, we also have monoterpenoids, sesquiterpenoids and so on!

So... Aside From Pretty Smells, What's the Big Deal?

Terpenes and terpenoids are much, much more than appealing fragrances and flavours. Dozens of scientific studies testify as to the diverse medicinal, biological and industrial potential of these simple compounds.

Of course, the industries that make the most use of terpenes are perfumery and food flavouring. Terpenes are also useful as cleaning agents and solvents, due to their ability to dissolve grease and oil. They are also useful as pesticides – which makes sense, as one of their primary functions in plants is pest defence.

But it's the medicinal potential of terpenes that's causing all the excitement right now. Terpenes may have antibacterial, anti-inflammatory, anti-anxiety, sedative, relaxant, or even anti-cancer effects! What's more, in combination with cannabinoids –compounds that are highly medicinally active too – their effects may be boosted in various intriguing ways.

Important Terpenoids & Terpenes in Cannabis

Mycrene - Monoterpene

● Peppery, fresh, herbaceous aroma - Hops, mango, lemongrass, thyme and cardamom

● Indica-dominant cannabis varieties

● May interact with THC to cause "couchlock" effect

● Motor relaxant and sedative effects

● 1992 and 2009 studies demonstrated antimutagenic effects

Limonene - Monoterpene

● Strong orange aroma

● Lemon, orange, grapefruit, lemongrass, verbena

● Sativa-dominant cannabis varieties

● May interact with CBD to produce powerful anti-acne effects

● Can kill breast cancer cells

● May treat gastrooesophageal reflux

Pinene - Monoterpene

● Woody, pine, resinous aroma

● Coniferous trees, camphorwood, sage, some citrus

● Present in most cannabis strains, generally higher in sativa

● Has anti-inflammatory, bronchodilatory and memory-boosting effects

● Antibiotic, effective at killing MRSA

Caryophyllene

● Sesquiterpene

● Peppery, spicy aroma

● Cloves, black pepper, rosemary, sage, hops

● Caryophyllene oxide is the compound detected by drug-sniffing dogs

● Interacts with the CB2 receptor and is actually classed as a cannabinoid!

● Anti-inflammatory, pain-relieving, neuroprotective, anti-anxiety, antidepressant, and anti-alcoholism properties

Linalool

● Monoterpenoid

● Floral, slightly spicy aroma

● Lavender, mint, rose, jasmine, laurel, birch, coriander

● Possibly higher in purple strains of cannabis

● May interact with CBD to produce powerful anti-acne effects

● May cause damage to human skin in high concentrations

Geraniol

● Monoterpenoid

● Floral, fruity scent

● Rose, geranium, lemongrass, peach, apple, grape, sassafras

● Plants use geraniol as a precursor to make many other terpenoids

● May have anti-inflammatory, analgesic, antibiotic and antifungal effects

Terpene & Cannabinoid Interactions

As you see, terpenes have multiple medicinal uses. But what's really exciting right now is the possibility that terpenes and cannabinioids could interact together to supply enhanced effects. Companies like Eybna, an Israeli startup specializing in terpenes in cannabis, are hard at work looking into these interactions and what they could mean for medical science.

For several decades, medical cannabis research focused mostly on the two most common cannabinoids, THC & CBD. Now, awareness of the importance of this unique group of compounds is starting to catch the industry's spotlight.

"Today, when you walk into a dispensary in Colorado or California and look on the labeling of the different cannabis products, you will most likely see the percentage of the main 3-4 terpenes found in it, in addition to the declaration of it's cannabinoid content. That's a good thing as a start, but there is much more then that, " explains Nadav Eyal, Co-Founder & CEO of Eybna Technologies - one of Israel's first medical cannabis startups. Eybna is researching terpenes and their effects together with industry leading Israeli academics, and specializes in the development of terpene-based solutions.

The prevailing assumption that the unique terpene composition of a specific cannabis phenotype is a main variable in determining its effect on the human body was explained by some of the most veteran scientist in the field: Dr. Lumír Hanuš was already writing about the chemical composition of terpenes in cannabis back in the 70's. Later on, in 2010, Dr. Ethan Russo published his findings about the possible pharmacological activities of cannabinoids and terpenoids. Unfortunately, all of these conclusions did not get much attention up until lately. This knowledge was just enough for Eybna to focus its R&D, which very quickly lead to the implementation of terpene technologies into consumable products.

"The demand for science-based terpene solutions has grown significantly in the last few years," Nadav continues. "Most of the inquiries we get are from highpurity cannabis oil producers wishing to restore the terpene content of their final products, after losing most of it during the extraction process. In the EU market, we work hand-in-hand with the biggest CBD brands, crafting their products with new qualities of smell, taste and potency while significantly improving their user experience - bringing the 'whole plant' principle back to the equation."

So let’s take a look at some of the interactions that have been discovered thus far.

Myrcene & THC

Myrcene is present in many varieties of cannabis that we traditionally call "indica" – the wide-leaved biotype that originates in the mountainous uplands of Afghanistan, Pakistan and parts of other nearby countries. For years, it was thought that the higher percentage of CBD often found in these strains was the cause of their famously sedative, "couch-lock" effect.

However, it turns out that that the compound these varieties have in common is not CBD, but myrcene! This monoterpene interacts with THC to produce an effect profoundly different than the racy, uplifting sensation caused by pure THC. It's not known exactly how this takes place, but the more we learn, the more we are finding that terpenoids can have some surprising effects on the endocannabinoid system.

Caryophyllene Is Actually A Cannabinoid!

Beta-caryophyllene is another important terpene – this time a sesquiterpene – present in many varieties of cannabis. Famously, it produces the compound detected by drug-sniffing dogs, caryophyllene oxide, on contact with air.

Scientists now know that caryophyllene also acts directly on the CB2 receptor, one of the main receptors of the endocannabinoid system. The CB2 receptors have important roles in regulating the immune and gastrointestinal systems, and also help regulate mood, sleep and other fundamental processes. Researchers now think that caryophyllene can have profound effects on anxiety and depression, among other things.

The science of terpenes in cannabis is in its infancy, and as research intensifies, we are likely to find a huge range of as-yet-known interactions between terpenes, cannabinoids and the signalling systems of the human body.