Terpenes 101

Imagine closing your eyes, sticking your nose into a bouquet of fresh beautiful buds (I’m not just talking about roses people), and inhaling the wonderful aromas of the plant. Have you ever wondered what it is that gives plants their aromatic smell or their delicious taste? If you have you’re in luck because this article is all about terpenes, and if you haven’t wondered what it is, stay tuned because you might actually learn something interesting. Terpenes not only contribute to a plants aromatic smell, they also have many other functions as well. Extraction artists are now using terpenes as additives in certain concentrated forms of cannabis to improve the smell, taste, and potency of the medicine. But first, before we get into that, let me start from the beginning. There is some chemistry involved in this, so for those of you that hated chemistry in high school, don’t flip the page just yet, I’ll make this part as painless and interesting as possible. Try to follow along, it gets easier, I promise. So first, to give you the background, here’s where the chemistry comes in, so stay with me…

What are terpenes and what is their purpose?

Terpenes are classified as organic compounds, which contain carbon and hydrogen atoms. They are a large class of organic hydrocarbons produced by a wide variety of plants as well as some insects and animals. Terpenes are considered to be made up of repeating units of a compound called isoprene. One isoprene unit, chain or ring, contains 5 carbon atoms with 8 hydrogen atoms attached, formula: C5H8 .

Ok, so why do you need to know about isoprenes? Isoprene units are one of nature’s common building blocks. The basic molecular formulas of terpenes are multiples of isoprene units. The amount of isoprene units in the terpene can effect what type of terpene it is.

True terpenes are usually grouped according to how many isoprene units are in the molecule. Here is a quick little chart to give you a little bit of an idea

  • Classification

  • Number of Isoprene units

  • Chemical Formula

  • Terpenes

  • Hemterpenes

  • 1 Isoprene Unit

  • C5 H8

  • N/A     Isoprene

  • Monoterpenes

  • 2 Isoprene Units

  • C10 H16

  • Geraniol, Limonene, Terpineol, Myrcene

  • Sesquiterpenes

  • 3 Isoprene Units

  • C15 H24

  • Humulene, Farnesenes, Farnesol

  • Diterpenesl

  • 4 Isoprene Units

  • C 20H 32

  • Cafestol, Kahweol, Cembrene, Taxadiene

  • Sesterterpenes

  • 5 Isoprene Units

  • C 25H40

  • Geranylfarnesol

  • Triterpenes

  • 6 Isoprene Units

  • C 30H48

  • Squalene

  • Sesquarterpenes

  • 7 Isoprene units

  • C35H56

  • Ferrugicadiol, tetraprenylcurcumene

  • Tetraterpenese

  • 8 Isoprene Units

  • C 40H64

  • Acycilclycopene, Monocyclic gamma-carotene, bicyclic alpha- and beta-carotenes

  • Polyterpenes

  • Many isoprene units

  • N/A

  • Gutta-percha

 

This type of information is kind of confusing; trust me I know, you should have seen me when I was researching this stuff. Unless you have some type of chemistry background (which I don’t) it seems like it’s all a little much to grasp. Right now you’re probably wondering where I’m going with this because I have yet to mention marijuana, don’t worry, we’ll get to that part. By the end of this article everything I’m telling you will tie in together and it will all make sense. But for now, let’s get back to terpenes.

Terpenes are the major components of essential oils and plant resin. They are aromatic compounds which contribute to the color, flavor, and the scent of different plants. They also provide the plant with natural protection from different environmental stresses including fungus, bacteria, and insects to name a few. The odor of the terpenes can attract pollinators, or repel the plants predators. In addition, some terpenes are known to have different medicinal values that work synergistically with cannabinoids to enhance the effects of the medicine.

Terpenes are produced in the trichomes of the plant by the same glands that produce THC. THC and the other cannabinoids are odorless, terpenes and terpinoids largely contribute to the unique smell of cannabis. The fragrance will depend on which terpene is predominate. They are very volatile molecules meaning they evaporate very easily and can be broken down by light, heat, and air. The yield of the terpenes in the plant can be affected by environmental factors, as well as the time of day, age, and maturation of the plant. When terpenes are denatured by oxidation, (drying and curing flowers), or chemically modified in some other way, they result in compounds referred to as terpenoids, (terpinoids contain additional functional groups).

Ok, I don’t want to bore you guys with weird words and confusing chemistry, but… to fully understand cannabis and its medicinal values you do need to know some of its chemistry. I hope you guys have been able to follow along so far. So now, on to terpene profiles….

Terpene Profiles

Scientists have characterized and identified the molecular structure of around 20,000 terpenes, making terpenes the largest category of plant chemicals. Out of these terpenes, there have been more than 120 found in cannabis. Even though only some of them appear in high concentrations, they have been found to have a number of benefits. Different strains of cannabis will have different terpene profiles. Terpene profiles are the distinct terpenes found in a particular plant or strain of cannabis. One plant or strain of cannabis can contain a number of different amounts of terpenes. The aromas a plant can have are determined by the terpene profiles, or the way terpene’s stack against each other.

Terpene profiles not only are affected by the genetics of the plant, but also by the plants environment. The levels of terpenes in the plant, or yields, of specific terpenes are affected by the plants environment. For example: The same variety of marijuana, grown in different types of soil or given different fertilizers, can produce different quantities and possibly even different types of oils. Combinations of cannabis genetics are endless, so the ranges of terpene profiles are immeasurable.

Although there have been a huge number of terpenes reported, there has only been a small minority that have actually been studied. Of the ones that have been studied, scientists have found them to have many medicinal values. Some evidence even suggests that we may be able to identify/verify the type of strain based on its terpene profile. Here are some examples of the primary terpenes found in cannabis and their characteristics.

Myrcene (monoterpene)

  • Boiling point:331-334 degrees F
  • Aroma/flavor: Earthy, musky, and fruity.
  • Most prevalent terpene found in marijuana.
  • Antimicrobial, antiseptic, analgesic, antioxidant, anti-carcinogen, anti-inflammatory, anti-tumor, anti-depressive properties.
  • Allows more THC to reach the brain cells and increases absorption of other terpenes by affecting the permeability of the cell membrane.
  • Also found in mangos, hops, bay leaves, lemon grass, eucalyptus, and many other plants.
  • High levels of myrcene in cannabis (.05% or higher) result in a more indica effect while lower amounts (under .05%) will produce a more energetic high.

Limonene (monoterpene)

  • Boiling point: 349 degrees F
  • Aroma/flavor: Citrus, Bitter in taste
  • Anti-fungal, antibacterial, anti-depressive, anti-anxiety, anticancer properties.
  • Also found in lemon, orange, tangerine, grapefruit and other citrus plants, as well as rosemary, juniper, peppermint, and many others.
  • Plants use limonene to repel predators.
  • Penetrates the cell membrane to promote the absorption of other terpenes and chemicals through the skin, digestive tract, and mucus membrane.
  • Has been used clinically to dissolve gallstones, improve mood, and relieve heartburn and gastrointestinal reflux.
  • Dominant in strains that have a pronounced sativa effect.

B-Caryophyllene (sesquiterpene)

  • Boiling point: 514 degrees F
  • Aroma/flavor: hoppy, sweet, woody, clove odor with a spicy, peppery taste.
  • Major terpene found in black pepper, cloves, and cotton
  • Antiseptic, antibacterial, antifungal, anti-tumor, and anti-inflammatory properties
  • Drug dogs are trained to find one molecule called caryophyllene-epoxide to sniff out marijuana.
  • Has the ability to interact with the body’s endocannabinoid system and bind directly to the cannabinoid receptor CB2

Pinene (Monoterpene)

  • Boiling point: 311 degrees F
  • Aroma/flavor: Pine
  • Also found in rosemary, sage, eucalyptus, and many others.
  • Anti-inflammatory, antiseptic, promotes alertness and memory retention, can increase mental focus and energy, and is also a bronchodilator among other things.
  • Most common, naturally occurring terpinoid in nature.

Terpineol (monoterpene)

  • Boiling point:426 degrees F
  • Aroma/flavor: lilac, citrus, apple blossom/ lime odor
  • Shown to be deeply sedating when inhaled
  • Also found in cypress, juniper berry, Ceylon cardamom, marjoram, thyme, and many others
  • Anti-bacterial, antiviral, and immune system stimulant
  • Used as fragrances in many soaps, perfumes, aromatherapy, and medicines

Humulene (sesquiterpene)

  • Boiling point: 223-225 degrees F
  • Aroma/flavor: Bitter, medium woody, hoppy
  • Powerful anti-inflammatory, analgesic, acts as an appetite suppressant, anti-cancer, anti-bacterial
  • Also found in hops, sage, ginseng and many others.

Geraniol (monoterpene)

  • Boiling point: 466 degrees F
  • Aroma/flavor: Floral, sweet, rosy, fruity with citrus to citronella like odor
  • Anti-oxidant, protective against neuropathy
  • Effective mosquito repellent
  • Also found in geraniums, citronella, mint, apple, pine, lemon, nutmeg, rose, and many others.

Valencene (Sesquiterpene)

  • Boiling point: 253 degrees F
  • Aroma/flavor: Citrus, grapefruit, woody, orange odor.
  • Anti-allergy, used in aromatherapy.
  • Also found in oranges, citrus fruits, mangos, and many more.

Terpinolene (Monoterpene)

  • Boiling point:361-428 degrees F
  • Aroma/Flavor: fresh woody, sweet, pine aroma, sweet citrus taste
  • Used as a flavor and fragrance agent in soaps, detergents, crèmes, lotions, and perfumes.
  • Been shown to exhibit antioxidant, anti-cancer effects, anti-fungal, anti-bacterial, has sedating effect
  • Been shown to repel mosquitoes and weevils
  • Also found in apple, cumin, lilac, tea tree and many others.

Ocimene (Monoterpene)

  • Boiling point: 212 degrees F
  • Aroma/flavor: Fruity, floral aroma
  • Used in perfumes
  • Antiseptic, antiviral, anti-fungal
  • Acts as part of the plants defense
  • Also found in Basil, hops, mango, mint, lavender, and more.

Linalool (Monoterpene)

  • Boiling point:388 degrees F
  • Aroma/flavor: Flora with a hint of spice
  • Anti-inflammatory, anticonvulsant, helps modulate motor movements, anti-anxiety, amplifies serotonin-receptor transmission, antidepressant, sedative effects, analgesic, and more
  • Vapors have been shown to be an effective insecticide against fruit flies, fleas, and cockroaches.
  • Also found in lavender, floral (spring flowers) , mint, cinnamon and more

So, you’re probably wondering why these terpenes are so important, I mean yeah they have medicinal values but what about the way they affect your high. After all it’s just the THC that gets you high rite? WRONG! Terpenes can affect the way animals and plants react to them by forming bonds with different molecules. As I said before these terpenes work synergistically with cannabinoids. Some can even bind directly to your body’s CB1 and or CB2 receptors (part of our body’s endocannabinoid system). This can cause a range of different therapeutic effects and also improves the effects of THC. There have been studies done which suggest that 100% THC is not as effective as a terpene infused cannabis resin. Because of this discovery, extraction artists are becoming more and more interested in terpenes. When making oil, shatter, wax etc. most of the terpenes from the plant are lost in the process. This is why people are now using processes like fractional distillation, vapor distillation, and/or steam distillation to extract terpenes from different plants. By doing this they are able to add them to their concentrates producing a better smelling, better tasting, and more potent medicine.

Alright, I know I’ve overloaded you guys with a lot of information, thanks for sticking with me. Hopefully you guys learned something! So many terpenes have not yet been studied and the evidence found from the ones that have been is huge. Scientists need to continue to study these terpenes to find out their medicinal values and effects. So keep an eye, or should I say nose, out for them. Next time you go to peel a succulent orange, or break up that enticing bud of Super Lemon Haze to smoke, you’ll know that delicious citrusy smell tantalizing your nostrils is primarily the wonderful terpene limonene.

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