07 March 2015

Cannabis: Terpenes and Their Effects

Terpene1 - any of a large group of volatile unsaturated hydrocarbons found in the essential oils of plants, including cannabis (with over 120 terpenes) which play a large part in the aromas and flavours of plants. Cannabinoids are a class of terpenophenolic (part terpenoid, part phenol) compounds. While terpenes are hydrocarbon groups created by various combinations of the isoprene units that make them up, and may be aromatic, all phenols are aromatic hydrocarbons, which means they have a very pronounced aroma. Terpenoids are compounds related to terpenes but may also include oxygen or have molecules rearranged; the terms are often used interchangeably. Cannabinoids, being half terpene and half phenol, have very pronounced aromas and flavours.

Cannabinoids were originally believed to only exist in family Cannabaceae, but have since been found in other families of plants such as Linaceae (flax), Asteraceae (echinaceae and helichrysum) and at least a dozen plants containing cannabidiol (CBD) have been identified. Not surprisingly, the heated/vaporised 'smoke' of cannabis contains up to 50% terpenes (primary terpenes and terpenoids identified in cannabis are limonene, myrcene, pinene, linalool, eucalyptol, γ-terpinene, β-caryophyllene, caryophyllene oxide, nerolidol and phytol), with cannabinoids usually accounting for 10-20% and others accounting for a further 10-30%. The wide array of medicinal properties of terpenes and the fact that each has many different medical benefits gives rise to the overlapping synergies between them; the strategy of deliberately overlapping benefits greatly increases the chances of good results in treatment. Different strains of cannabis contain different amounts of the various terpenes (including cannabinoids). As a result, different diseases and disorders are more effectively treated by some strains than others.

Jack Herer (strain) Cannabinoid and Terpenoid Profile

At harvest, cannabis contains about 1% essential oil, composed mostly of very volatile monoterpenes2 (80-90%) that evaporate very quickly. Once completely dry, the amount of essential oil is only 0.1% and about 50% of that is sesquiterpenes which are far less volatile. More than 100 different terpenes have been detected in cannabis, but many more are available if variants of each are considered. Terpenes are a major component of essential oils and aromatherapy uses the medicinal properties to regulate mood, address sleep problems, improve acuity and overall health. For example, the essential oil from lavender is calming and relaxing, while rosemary essential oil increases concentration and produces a feeling of well being. It is possible to make essential cannabis oil through steam extraction to use in perfumes, cosmetics, soaps, candles and also as a flavouring agent in cooking, for candies and beverages.

Hops, a member of the family Cannabaceae
ß-Myrcene (Myrcene)
Boiling Point: 168°C (334°F)
Decarboxylation3 Point: 115-145°C (239-293°F)
Myrcene, from Myrcia sphaerocarpa (Brazilian medicinal shrub). A folk remedy for treating type 2 diabetes, dysentery, diarrhoea and hypertension, a 1997 study in Switzerland analysed various cannabis strains for terpenes and found myrcene to be the most abundant (others included pinene, limonene, carene, humulene, bergamotene, terpinolene and caryophyllene). Myrcene is a monoterpene and is crucial in the formation of other terpenes. Found in mango, hops, bay leaves, eucalyptus, lemongrass and many other plants, it smells similar to cloves, with a herbal, balsamic, spicy aroma.
*analgaesic (pain relief) in synergy with ∆9-Tetrahydrocannabinol (THC) *antibacterial *anti-diabetic (stabilises / controls blood glucose levels among diabetics) *anti-inflammatory in synergy with ∆1-Tetrahydrocannabinolic Acid (THC-A) *anti-insomnia (sedative effect to aid sleep) *anti-proliferative / anti-mutagenic (inhibits cancer cell growth and cell mutation) *anti-psychotic / calmative in synergy with CBD and linalool, to relax mentally and physically *anti-spasmodic in synergy with THC, THC-A and CBD.
Myrcene has properties that lower resistance across the blood/brain (hemato encaphalic) barrier, allowing it and many other chemicals to cross the barrier more easily and quickly. In the case of cannabinoids, like THC, it allows it to take effect more quickly. More uniquely still, myrcene can increase the maximum saturation level of the CB14 receptor, allowing for maximum psychoactive effect. For most people, the consumption of a fresh mango, 45 minutes before inhaling cannabis, will result in a faster onset of psychoactivity and greater intensity (myrcene acts in synergy with THC). 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 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%.

D-Limonene (Limonene)
Boiling Point: 176°C (349°F)
Limonene is an abundant monoterpene present in cannabis (second only to myrcene) with a strong citrus odour and a tangy, bitter taste. Unsurprisingly, limonene is most commonly found in highest concentrations in the rinds of citrus. Used in alternative medicine, it has the ability to reduce heartburn and gastric acid reflux; is used widely as a flavour additive in food production, is a common aroma compound in perfumery and the main active ingredient in citrus cleaners. A natural, renewable solvent in cleaning products due to its ability to dissolve oils and other lipids; it is capable of stripping paint and is considered an effective substitute for turpentine (must be handled with care as at high concentrations it can act as an irritant). A major reason for limonene’s widespread use is its very low toxicity to humans.
*aids digestion *antidepressant *anti-fungal (particularly toenail fungus, athlete's foot, yeast infections) *anti-inflammatory *anti-proliferative (inhibits cancer cell growth) *anxiolytic (relieves anxiety) *immuno-stimulant (similar to garlic) *increases attention, mental focus, well-being and the human sex drive *prevents gastric distress *promotes weight loss *protects from aspergillus (a common infective fungus/mould) *protects from carcinogens in smoke *topical antiseptic agent *treats gastric acid reflux and oesophageal ulcers.
Limonene quickly and easily penetrates the blood-brain (hemato encaphalic) barrier which increases systolic pressure. Limonene assists in absorption of other terpenoids and chemicals through skin, mucous membranes and digestive tract. Limonene is one of two major compounds formed from α-Pinene.

Pinene (α-pinene and β-pinene)
Boiling Point: 155°C (311°F)
Pinene is one of the most common monoterpenes which occurs naturally as two isomers8 (α-pinene and β-pinene). Usually sourced from turpentine (dry distillation of coniferous wood) α-pinene makes up 58-65% and β-pinene around 30%. Found in cannabis, pines and other conifers, sage (salvia), sagebrush (artemisia) and eucalyptus, α-pinene is also found in olive, rosemary (memory herb), sassafras, bergamot and β-pinene is also found in hops and cumin. Pinene has been used for centuries in 'alternative' medicine.
*analgaesic (pain relief) *antibacterial *antibiotic *anti-inflammatory *antioxidant (prevents oxidation damage to other molecules in the body) *anti-proliferative (inhibits cancer cell growth) *apoptosis5 *bronchodilator *expectorant
It also crosses the blood-brain (hemato encaphalic) barrier very easily, where it acts to prevent destruction of molecules responsible for transmission of information which results in memory improvement. This terpene, in part, counteracts the effects of THC. The result is that memory fails more with pure THC than with THC mixed with pinene. 'Skunk' strains are recognised for their high levels of pinenes.

βeta–Caryophyllene (β–Caryophyllene)
Boiling Point: 160°C (320°F)
Black peppercorns
β–Caryophyllene, a sesquiterpene is found in many plants including, Thai basil, cloves, rosemary and black pepper, with a rich spicy odour and flavour. This terpene selectively binds to the CB26 receptor and is a functional CB2 agonist7. Intriguingly, β–Caryophyllene is a common constituent of the essential oils of numerous spice and food plants and a major component in cannabis, even though it is not a cannabinoid. Some sources speculate that β–Caryophyllene is so powerful it could threaten existing pharmaceuticals, and synthetic cannabinoids currently being developed.
*active ingredient in cloves and a remedy for toothache *analgaesic (pain relief) *antibacterial *antidepressant *antifungal *anti-inflammatory *antioxidant *antiseptic *anti-proliferative (inhibits cancer cell growth) *anxiolytic (relieves anxiety) *neuroprotective (slows damage to nervous system and brain).
Caryophyllene oxide is the substance in cannabis that is identifiable by drug-sniffing dogs.

Terpinolene (γ-terpinene)
Boiling Point: 183-220°C (361-428°F)
Terpinolene, a monoterpene, has a smoky or woody odour and is found in apple, cumin, lilac, tea tree, various citrus fruits and herbs such as oregano and marjoram.
*anti-bacterial *anti-fungal *anti-insomnia (sedative effect to aid sleep in cancer treatment in synergy with linalool and cannabinol, CBN) *antioxidant *anti-proliferative (inhibits cancer cell growth).
Terpinolene has been shown to be an effective natural method to repel both mosquitoes and weevils and is often found in cannabis strains that have a high level of pinenes, and these aromas can hide the terpinolene scent.

Boiling Point: 213°C (451°F)
Borneol is a monoterpene described as having a minty, spicy, cooling, herbal aroma and is found in high concentrations in camphor, rosemary and mint. Used in Chinese traditional medicine alongside acupuncture, topically and orally since the late 1600's, the first mention by western doctors was in 1888 at Edinburgh University. Borneol is a natural insect repellent, preventing disease being passed by mosquitoes (effective disease vector control method for West Nile and other mosquito borne pathogens), fleas and other pests.
*analgaesic (pain relief) *antibacterial *anti-fibrosis (balance body’s fibrosis response to injury) *anti-fungal *anti-inflammatory *antioxidant.

β–Linalool (Linalool)
Boiling Point: 198°C (388°F)
Linalool is best known for the pleasant floral odour it gives hundreds of different plants including lavender, citrus, cinnamon, laurel, birch, coriander and rosewood. Linalool has been used for thousands of years as a calmative and sleep aid (partly responsible for sedative effects of certain cannabis strains) and is a critical precursor in the formation of Vitamin E.
*analgaesic (pain relief) *anti-depressant *anti-epileptic agent *anti-inflammatory *anti-proliferative (inhibits cancer cell growth) *anxiolytic (relieves anxiety).
Its vapours are an effective insecticide against fruit flies, fleas and cockroaches.

Eucalyptol (1,8 Cineole or Cineole)
Boiling Point: 176°C (348.8° F)
Eucalyptol is a monoterpene, the primary terpene of eucalyptus trees and found in high concentrations in tea trees, mugwort, bay leaves, basil, sage, cannabis and as an ingredient in mouthwash and cough suppressants. It's the characteristic smell of the 'gum' tree.
*analgaesic (pain relief) *anti-bacterial *anti-inflammatory *anti-fungal *antioxidant *anti-proliferative (inhibits cancer cell growth) *controls airway mucus hyper-secretion and asthma *effective treatment for sinusitis *improves concentration and meditation *kills leukaemia cells in vitro *reduces inflammation *taken orally (inhaled, tincture, eaten) *topically on skin and gums.
Eucalyptol has been found to play an important role in the sensory perception of 'eucalyptus' character in some wines. Eucalyptol is an anti-fungal, but despite that, a fungus has been discovered that produces eucalyptol in large amounts which have potential for use in future biofuels.

Nerolidol (known as Peruviol)
Nerolidol is a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers. Nerolidol, with a woody, fresh bark aroma, can be found in neroli (orange flower), ginger, jasmine, niaouli and citronella.
*anti-fungal *anti-leishmaniasis (Leishmaniases are diseases caused by protozoan parasites, transmitted to humans by the bites of infected female sandflies) *anti-malarial *sedative effect.
Nerolidol is currently being investigated as a facilitator for transdermal delivery of drugs (due to its ability to penetrate the skin) and as an inhibitor of Leishmania protozoa.
Vietnamese coriander

α-Humulene (Humulene or α–Caryophyllene)
Boiling Point: 198°C (388°F)
Humulene is a sesquiterpene found in common hops (Humulus lupulus) from which it gets its name. Also found in cannabis, sage, ginseng, Vietnamese coriander and gives beer its ‘hoppy’ aroma, it is well-known to Chinese medicine.
*analgaesic (pain relief) *anti-bacterial *anti-inflammatory (when blended with β–Caryophyllene) *anti-proliferative (inhibits cancer cell growth).
Humulene is unique because, like Tetrahydrocannabivarin (THCv), it acts as an appetite suppressant, making it promising for weight loss treatments.

Phytol is another interesting terpene, different from most others, offering more medicinal options to patients. Phytol is one of the breakdown products of decomposed chlorophyll. Its aroma is floral and balsamic in nature and it is an ingredient of fragrances.
*immuno-suppressant *topical to reduce itching and treat slow-healing tissue wounds.
Phytol is a non-toxic yellow pigment suitable for dying foodstuffs and is used in manufacturing synthetic Vitamins E and K.

Pure Terpenes (Mark Heinrich)
The endless profile possibilities of terpenes are responsible for the variations in taste and effects of cannabis. Some combinations of terpenes can act in synergy (the effects are added) while others are antagonists (the effects inhibit each other). Some terpenes increase the assimilation of THC, while others affect the flow of dopamine and serotonin, two of the main regulators of mood and behaviour.

Unfortunately, current chromatography techniques do not allow accurate identification of all terpenes present in cannabis. This diversity offered by nature is impossible to reproduce for the pharmaceutical industry which attempts to isolate the active principles in order to patent synthetic reproduction. Pure THC causes very different effects than whole cannabis because it is missing all the other cannabinoids and terpenes that modulate its effects. A plant’s age, maturity and time of harvest may also modulate levels of terpenes. Usually, the smell becomes more intense during flowering, but it can vary depending on weather conditions, environment (fertilisers for example) and even plant stress. For example, the scent of a plant is usually stronger at dawn rather than at dusk. Terpenes are responsible for both the flavour and aroma of plants and it is important to remember that a plant with little aroma will always have little flavour.

Glossary of Some Terms
1. Terpene - One of a class of hydrocarbons with an empiric formula of C10H16, occurring in essential oils and resins. Terpenes containing 15, 20, 30, 40 etc, carbon atoms are called sesquiterpenes, diterpenes, triterpenes, tetraterpenes etc
2. Monoterpenes - Hydrocarbons or their derivatives formed by the condensation of two isoprene units, and therefore containing 10 carbon atoms
3. Decarboxylation - a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain.
4. CB1 - cannabinoid receptor type 1 is a G protein-coupled cannabinoid receptor located primarily in the central and peripheral nervous system
5. Apoptosis - Genetically directed cell self-destruction marked by fragmentation of nuclear DNA, activated either by presence of stimulus or removal of suppressing agent or stimulus, and is normal physiological process eliminating DNA-damaged, superfluous, or unwanted cells
6. CB2 - cannabinoid receptor type 2 expressed in the immune system
7. Agonist - a substance which initiates a physiological response when combined with a receptor
8. Isomers - molecules with the same chemical formula but different structures


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  2. Phytol isolated from the leaves of Black tea. It attenuates the inflammatory response by inhibiting neutrophil migration, which is partly caused by reduction in IL-1β and TNF-α levels and oxidative stress. Phytol