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.
Therapeutically
*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.
 |
| Lemongrass |
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.
Therapeutically
*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.
Therapeutically
*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.
Therapeutically
*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.
 |
Lilac
|
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.
Therapeutically
*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.
 |
| Mint |
Borneol
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.
Therapeutically
*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.
Therapeutically
*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.
Therapeutically
*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.
 |
| Neroli |
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.
Therapeutically
*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.
Therapeutically
*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.
Therapeutically
*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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