Alibi V.29 No.5 • Jan 30-Feb 5, 2020 

Cannabis Manual

Better Together

Terpenes, cannabinoids and the entourage effect

better together
If you sense that cannabis is greater than the sum of its parts, you’re already well on your way to understanding the so-called entourage effect. Discussion of the entourage effect as it concerns cannabis use centers on the complementary, synergistic nature (and resulting effects) of common volatile organic compounds known as terpenes that work in concert with cannabis plants’ natural phytocannabinoids.

Terpenes are a diverse class of organic elements produced by flora, notably conifers and cannabis (as well as some insects), that serve as a protective mechanism for the plants, deterring herbivores with intense scents that also attract predators and parasites of said herbivores. Of the approximately 20,000 terpenes extant on Earth, cannabis plants boast more than 100. Cannabis’ inherent terpenes—including caryophyllene, humulene, limonene, linalool, myrcene, ocimene, pinene, terpinolene—are not unique to cannabis.

Cannabis’ whole plant synergistic effects involve those terpenes working in tandem with the phytocannabinoids. Researchers have isolated close to 150 of these organic, bioactive elements—from undisputed phytocannabinoid all-star delta-9-tetrahydrocannabinol (THC) to anti-inflammatory cannabidiol (CBD) and far beyond. As cannabis medication and consumerism makes headway across the globe, so does our collective scientific understanding of phytocannabinoids, terpenes and some of the hows and whys of their interaction inside the mammalian brain.

To better visualize how cannabis acts on the human brain, let’s take a cursory look at the endocannabinoid system, which science from the past quarter-century has revealed plays vital roles in the development of the central nervous system, synaptic plasticity (or change that occurs at the junctions between neurons that facilitate neuronal communication) and our response to both endogenous and environmental insults. The endocannabinoid system is made up of cannabinoid receptors, endogenous cannabinoids and the enzymes responsible for synthesis and degradation of the aforementioned endocannabinoids. This system is vital for maintaining homeostasis.

Kelvin Rodolfo, Emeritus Professor of the Department of Earth and Environmental Sciences at the University of Illinois at Chicago, defines homeostasis as “how a person under conflicting stresses and motivations can maintain a stable condition.” To wit, a malfunctioning endocannabinoid system has been linked to issues and health conditions involving: appetite and digestion, metabolism, chronic pain, inflammation and other immune system responses, mood, learning and memory, motor control, sleep, cardiovascular system function, muscle formation, bone remodeling and growth, liver and reproductive system function and stress. In reference to endocannabinoids, “endo” refers to natural production in the human body and “cannabinoid” refers to a cannabis-like substance. The British Journal of Pharmacology published a review of our current scientific understanding of the entourage effect in “Taming THC: Potential cannabis synergy and phytocannabinoid-terpenoid entourage effects.”

In that review, author and doctor Ethan B. Russo reports that terpenes display “unique therapeutic effects that may contribute meaningfully to the entourage effects of cannabis-based medicinal extracts.” Russo describes terpenes and phytocannabinoids’ pharmacology-based potential for synergistic effects, referencing both CBD and CBG’s inhibition of the staph infection MRSA and theorizing enhanced effectiveness if CBD and CBG were to be combined with pinene, a terpene that also fights off MRSA, as well as terpenes that increase skin permeability. The review also posits the following synergistic interaction: pinene may help counteract memory issues caused by THC; caryophyllene may work in concert with CBD to benefit addiction treatment; limonene and CBD might work together to alleviate anxiety; and THC plus CBN could yield enhanced sedation.

Indeed, science is emerging at a consistent rate and pace that furthers our understanding. Earlier in the year 2020, on Jan. 6, Italian scientists published their discovery of a new phytocannabinoid in Scientific Reports. In “A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol,” researchers describe how their attempts to “define the phytocannabinoids profile that characterizes a medicinal cannabis variety” led to the accidental discovery of the naturally occurring THC homolog Δ9-Tetrahydrocannabiphorol, “a new phytocannabinoid with the same structure of Δ9-THC but with a seven-term alkyl side chain.”

As research into the entourage effect gains steam—produced largely by scientific perspiration and motivated by the profitability of commercial and medical cannabis—our collective understanding of individual terpenes and phytocannabinoids as well as their synergistic, collaborative effects may well provide new and innovative physiological and psychological applications for human medicine.

terpenes

Terpenes

Caryophyllene: This terpene possesses a woodsy, gingery, peppery scent, and it’s also a prime terpenoid in cinnamon, black pepper, sage and clove. Studies show that beta-caryophyllene (BCP) is in the sesquiterpene class, which consist of three isoprene units and possess 15 carbon atoms. University of Bonn scientists published “Beta-caryophyllene is a dietary cannabinoid” in 2008, confirming that “BCP selectively binds to the [THC] binding site ... in the CB2 receptor, leading to cellular activation and antiinflammatory effects.” As a functional CB2 agonist, BCP offers a pristine example of the entourage effect. Results of mice studies on analgesia and relief from anxiety encouraging. Strains reported to be high in BCP include the Cookies family—GSC, Platinum GSC and Candyland—OG Kush, Death Star and White Widow.

Humulene: This terpene is also of the sesquiterpene class. It shares a chemical formula with close relative beta-caryophyllene (BCP) but they are structured differently. Many plants containing BCP—including clove, basil and sage—also contain humulene and the two share a twinning scent profile. Named for the hops plant (aka Humulus lupulus), humulene exhibits antibacterial and anti-inflammatory traits and notably protects cannabis plants by deterring agricultural pests and staving off fungal infections. Humulene adds a specific, subtle earthy, woodsy, ever so slightly spicy aroma. Strains that feature humulene as third chair include Bubba Kush, Candyland, Death Star, GSC, Sour Diesel and White Widow.

Limonene: This monoterpene serves a defensive purpose for plants, a warning that wards off predation by invading insects in a variety of plants. Limonene is abundant in citrus fruit rinds (especially oranges and lemons) as well as in rosemary, peppermint, juniper and pine needles. It’s important to note that a lemony smell might not always be indicative of high limonene content. That said, give Super Lemon Haze, Lemon Kush and Lemon Skunk a try for some bright and sunny—and possibly even immune-boosting—limonene-y cannabis goodness.

Linalool: These two enantiomers (stereoisomers that mirror one another) of a natural terpene alcohol are found in more than 200 plant species, ranging from the families Lamiaceae (mint and other herbs), Lauraceae (laurels, cinnamon and rosewood) and Rutaceae (citrus fruit) to birch trees and other plants native to tropical to boreal climates, including fungi. Primary research and commercial applications have focused on linalool’s pleasant lavender-floral scent and its tendency to foster relaxation and improvement of mood. Strains such as Do-Si-Dos, Fire OG, Scooby Snacks and Zkittlez feature linalool most prominently.

Myrcene: This terpene is common to and dominant in many recreational and medical cannabis strains as well as being present in hops, mango, lemongrass and thyme. For a strain that’s high in myrcene—which is believed to promote calming effects and possess anti-inflammatory, antibiotic, antimutagenic, analgesic and sedative properties—give OG Kush, Blue Dream, Grape Ape, Granddaddy Purps, Tangie or Harlequin a try.

Ocimene: This terpene is responsible for the sweet, herbaceous flavors and woody or citrus undertones of certain cannabis strains. Ocimene is also found in parsley, mint and orchids and while our current knowledge of the terpene indicates that its primary palliative effects are caused by its exquisite, earthy aroma, featured prominently in many commercial perfumes, we may learn still more about the science of this uplifting terpene in the future. For ocimene-y strains, consider Amnesia and Dutch Treat.

Pinene: While myrcene tends to dominate in the cannabis world, this terpene is the most common terpene in the overarching natural world. It smells like a deep breath taken in a pine forest and is also a constituent of orange peel, turpentine, pine needles, rosemary, dill, basil and parsley. Research into pinene’s effects indicate the following effects: anti-inflammatory, anti-anxiety, a bronchodilator (helps to open airways), pain relief and to combat THC-associated short-term memory impairment. For a pinene-y buzz, go for strains such as Snoop’s Dream, Cannatonic, Cotton Candy Kush, Critical Mass, God’s Gift, Grape Ape, Harlequin and Kosher Tangie.

Terpinolene: This terpene, contrariwise, is probably the least pervasive in both the realm of cannabis and the larger natural world but it still contributes mightily to the taste, flavor and even effects of cannabis strains. It is believed to produce uplifting psychological effects and exhibit antibacterial and antifungal properties. Terpinolene is also present in plants that range from lilac, tea tree and nutmeg to cumin and apples. To sample terpinolene in cannabis strains, seek out Dutch Treat, Jack Herer, XJ-13, Golden Pineapple, Golden Goat, Ghost Train Haze and Orange Cookies.

 
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