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Cannabinoids, Terpenes & Flavonoids

Dr Raphael Mechoulam


Discovery of THC in 1964, Anandamide in 1992


"Cannabis 101" - Terpenes


Cannabinoid Profiles:

Cannabinoids


THC

Tetrahydrocannabinol




ANANDAMIDE

First isolated in 1992, Anandamide is a neurotransmitter and endocannabinoid, meaning a cannabinoid produced within the body. Anandamide, also known as N-Arachidonoylethanolamine or AEA, is an endogenous cannabinoid that acts as a “key” molecule fitting into the “locks” of the CB1 and CB2 receptors around the body. It’s name is taken from the Sanskrit word ananda, which means bliss, and the word amide, which refers to a type of acid found within the body. Anandamide is thus the bliss amide, though it is more widely called the bliss compound (not to be confused with the spirit molecule, DMT). Very appropriate to the Sanskrit origins of its name, anandamide has been shown to be boosted by doing yoga, which may explain why those yogis are so calm and blissful all the time. Similarly, an anandamide deficiency has been shown to increase anxiety and stress. Anandamide can be thought of as the body’s version of THC, because it has many of the same therapeutic effects and if it weren’t for the presence of anandamide in the body we wouldn’t have the CB1 and CB2 receptors that all cannabinoids interact with. Anandamide doesn’t exist solely in the human body. Outside of the body this endocannabinoid can be found in chocolate. So next time you’re enjoying a chocolate bar, allow that anandamide to jog your memory, and enjoy those sweet cannabinoids.

  • Analgesic – Relieves pain.
  • Angiogenic – Causes new blood vessels to form from pre-existing blood vessels.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Anxiolytic – Relieves anxiety.
  • Euphoriant – Produces feelings of euphoria, promotes happiness and relaxation.
  • Neurogenic – Promotes the growth of new brain cells. Specifically within the Hippocampus, an area of the brain responsible for memory and spatial awareness (just like CBD).

  • THCa

    Tetrahydrocannabinolic Acid

    THCA is the main constituent in raw cannabis. THCA converts to Δ9-THC when burned, vaporized, or heated at a certain temperature. THCA, CBDA, CBGA, and other acidic cannabinoids hold the most COX-1 and COX-2 inhibition, contributing to cannabis’ anti-inflammatory effects. This cannabinoid also acts as an antiproliferative and antispasmodic.
    Found in the trichomes, Tetrahydrocannabinolic acid (THCa) is the acidic precursor to THC, which actually exists in only minute quantities in the living plant. In living cannabis, THCa is the most abundant cannabinoid and terpenoid, potentially reaching over 30% of the dry weight of any cannabis plant. Immediately after harvest, the THCa begins to be converted into THC, a process quickened by exposure to heat and sunlight. One main reason cannabis is cured is to convert the THCa into THC, as well as drying it out to make it easier to burn, thus releasing the remaining THCa as THC. Knowing about decarboxylating cannabis is crucial in making edibles, where one pre-cooks the bud before making it into butter to raise the potency by converting THCa into THC. Like all cannabinoids that exist in the living cannabis plant, THCa is non-psychoactive, though it still stimulates the appetite like THC. It also is a powerful anti-inflammatory, helps fight cancer and other tumors, aids with sleep, and more. Also like THC, an oral test has already been developed to detect THCa. While some sources show THCa to be a stable compound, Aphios research chemicals claims that it is very unstable and will breakdown into THC within weeks. It may have to do with the preparation of synthesized THCa used in their laboratory versus an active live-plant based THCa, but without further research the stability of THCa and how quickly it converts to THC is unknown.

  • Analgesic – Relieves pain.
  • Anti-Emetic – Reduces vomiting and nausea.
  • Anti-Inflammatory – Reduces inflammation.
  • Anti-Insomnia – Aids with sleep.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Antispasmodic – Suppresses muscle spasms.
  • Modulates Immune System – THCa has been shown to both improve and potentially suppress the immune system functions.
  • Neuroprotective – Slows damage to the nervous system and brain.

  • THCv

    Tetrahydrocannabivarin

    THCv is a minor cannabinoid found in only some strains of cannabis. The only structural difference between THCv and THC is the presence of a propyl (3 carbon) group, rather than a pentyl (5 carbon) group, on the molecule. Though this variation may seem subtle, it causes THCV to produce very different effects than THC. These effects include a reduction in panic attacks, suppression of appetite, and the promotion of bone growth.
    THCv is a non-psychoactive variant of THC. The other major difference between the two is that instead of stimulating appetite, the famed ‘munchies,’ THCv actually suppresses appetite. For that reason THCv is being heavily researched as a weight loss tool. Like many cannabinoids it is an anti-inflammatory and an analgesic, though less strong than CBD and THC, but using different mechanisms in the body.

  • Analgesic – Relieves pain.
  • Anorectic – Appetite suppressant, promotes weight loss.
  • Anti-Emetic – Reduces vomiting and nausea.
  • Anti-Epileptic – Reduces seizures and convulsions.
  • Anti-Inflammatory – Reduces inflammation systemically.
  • Bone Stimulant – Promotes bone growth.
  • Euphoriant – Produces feelings of euphoria, promotes happiness and relaxation.
  • Currently Being Studied For:

  • Diabetes: A combination CDB/THCv tincture is in a phase 2 clinical trial as a way to mitigate diabetes. GW Pharmaceuticals, a British company, is a world leader in cannabis research. GW is presently examining CBD/THCv’s abilities to ameliorate insulin sensitivity.
  • Weight Loss: The same mechanisms that allow THCv to combat diabetes combined with THCv’s anorectic properties make it an effective way to combat obesity and control weight gain. GW Pharmaceuticals is also leading this research. GW believes in THCv so much they have even patented its abilities to combat weight gaining and diabetes.
  • Parkinson’s Disease: THCv is a cannabinoid that has been identified that can aid in Parkinson’s Disease by attenuating the motor inhibition caused by 6-hydroxydopamine. It also has various related mechanisms that assist in treating Parkinson’s.
  • Anti-Inflammatory: This study was only done on mice but if other studies are any indication of success it should apply similarly to humans, but THCv shows to be an anti-inflammatory. It works through a different mechanism than other anti-inflammatory drugs, THCv inhibits cyclic AMP production by hCB(2) CHO cells, but does not inhibit other affiliated cells. The whole thing seemed to rely on the CB 2 receptors.

  • CBC

    Cannabichromene

    Evidence has suggested that it may play a role in the anti-inflammatory and anti-viral effects of cannabis, and may contribute to the overall analgesic effects of medical cannabis. A study done in March 2010 showed that CBC along with cannabidiol (CBD) and tetrahydrocannabinol (THC) have antidepressant effects. Another study showed that CBC helps promote neurogenesis.
    Cannabichromene is a little understood non-psychoactive cannabinoid that has recently been the subject of much greater scrutiny. Like THC and CBD, CBC is an end product of CBG being processed into CBGa, and then into other cannabinoids. As a result, CBC has the same chemical formula and weight as CBD and THC but differs from its chemical cousins by the arrangement of its atoms. The heretofore lack of research hasn’t stopped it from being the subject of multiple patents recognizing its wide range of medical uses. Like THC and CBD, CBC is an analgesic and anti-inflammatory, although less potent than these more famous molecules. It is also antibacterial and its variant CBCa has been shown to be an antifungal agent. Like CBD, cannabichomene is both a bone stimulant and neurogenic compound, helping grow both body and mind. Perhaps its most important use is as an anti-proliferative, slowing tumor growth and combating cancer, just like CBD and THC. CBC has also been shown to be ten times as powerful as CBD at reducing anxiety and stress.

  • Analgesic – Relieves pain.
  • Antidepressant – Relieves symptoms of depression.
  • Antifungal – Inhibits the growth of fungus.
  • Anxiolitic – Relieves anxiety.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Bone Stimulant – Promotes bone growth.
  • Neurogenesis – Promotes the growth of new brain cells.
  • Cannabichromene


    CBD

    Cannabidiol

    Must know facts about Cannabidiol (CBD)
    Study: Topical CBD treatment may reduce central nervous system inflammation.
    Study: Cannabidiol (CBD) May prevent Degenerative Disc Disease

    Not all cannabinoids are colorless. One of the most brightly yellow-colored cannabinoids is CBD, a very valuable cannabinoid. CBD has tremendous medical potential. This is particularly true when the correct ratio of CBD to THC is applied to treat a particular condition. CBD acts as an antagonist at both the CB1 and CB2 receptors, yet it has a low binding affinity for both. This suggests that CBD’s mechanism of action is mediated by other receptors in the brain and body.

    Cannabidiol (CBD) is one of the most common non-psychoactive cannabinoids in the cannabis plant, occurring in the largest concentrations after THC and THCa. The reason THC is psychoactive is because it interacts with the CB1 receptor. CBD, on the other hand, has no interaction with the CB1 receptor and instead uses a bunch of other receptor sites. In an interesting reversal of CBD’s ability to calm THC psychoactivity, there is a way to transform CBD into THC. Aside from being non-psychoactive, CBD is a powerful treatment for seizures, pain, inflammation, cancer, auto immune diseases, and numerous other conditions. While THC is also an analgesic and anti-inflammatory, CBD has been shown to even more potent than THC and pharmaceutical drugs. While THC and CBD both cause the user to feel less pain they use entirely different mechanisms of action. THC helps with pain by helping one forget they are in pain, or by distracting them from your pain. CBD works to reduce the amount of pain felt whenever you are hurt, more similar to traditional opiate pain killers. Due to the fact that it is non-psychoactive and has a wide range of medical uses, CBD is highly recommended for treatment of children, the elderly, and anyone who wants to remain clear headed while still getting the medical benefits of cannabis. CBD appears to change how THC affects the body, making it less psychoactive yet preserving the therapeutic benefits. Many people who are new to cannabis edibles report getting too high and having negative experiences, if this ever happens to you, use a CBD-rich tincture to calm down the psychoactive effects of THC and help you sober up. The vast medical benefits coupled with the lack of psychoactivity have prompted over a dozen states to pass CBD-only medical cannabis laws, legalizing a part of the plant while keeping the whole plant illegal. This does a dis-service to patients because even patient who need a CBD-rich regimen of medicine often need THC, THCa, or CBG; pediatric epilepsy patients use very high ratios of CBD:THC, in the range of 28:1, yet they still need THC at times and can see benefits from using THCa and CBG. Combining different cannabinoids together has been shown to have a stronger effect than any of those cannabinoids would have had on their own, this effect has been called the Entourage Effect. Many companies are attempting to cash in on the CBD Green Rush and have put numerous inferior products on the market for inflated prices, ProjectCBD has called these Snake Oil Salesmen “Hemp Oil Hustlers.” The problem has become so bad that in February of 2015, the FDA sent warning letters to numerous companies informing them that their CBD products did not test as high as they claimed and that they are not FDA approved.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-Diabetic – CBD is the only cannabinoid identified that helps lower blood sugar levels.
  • Antidepressant – Relieves symptoms of depression.
  • Anti-Emetic – Reduces vomiting and nausea.
  • Anti-Epileptic – Reduces seizures and convulsions.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Insomnia – Aids with sleep.
  • Anti-Ischemic – CBD is the only cannabinoid identified that reduces the risk of artery blockage.
  • Antipsioratic – CBD is the only cannabinoid identified to treat psoriasis.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Antipsychotic – Tranquilizing effects to relieve symptoms of psychosis, two terpenoids also help (linalool and myrcene).
  • Antioxidant – Prevents the damage of oxidation to other molecules in the body.
  • Antispasmodic – Suppresses muscle spasms.
  • Anxiolitic – CBD is the only cannabinoid identified that relieves anxiety, but two terpenoids also help (linalool and limonene).
  • Bone Stimulant – Promotes bone growth.
  • Immunosuppressive – CBD is the only cannabinoid identified that reduces function in the immune system.
  • Intestinal Anti-Prokinetic – CBD is the only cannabinoid identified that reduces small intestine contractions.
  • Neuroprotective – Slows damage to the nervous system and brain.
  • Vasorelaxant– CBD is the only cannabinoid identified that reduces vascular tension.
  • CBD is also currently being studied for a variety of conditions.
  • Currently Being Studied For:

  • Alzheimer’s Disease/Dementia/Memory Loss: CBD’s strong neuroprotective and antioxidative effects work together to counteract the effects of aging on our brains, fighting off memory loss and dementia.
  • Bone Healing: New research from March 2015 has shown that CBD’s ability to stimulate bone growth is powerful enough to speed up and enhance the healing of broken bones. The same study found that THC had a related role in the healing of broken bones, working in entourage with CBD.
  • Cancer: A study was published in 2007, regarding ongoing research being done at San Francisco’s California Pacific Medical Center, showing that CBD inhibits a particular gene (Id-1) which is responsible for the growth of cancer cells in the body. By inhibiting this gene CBD shuts down the growth of cancer cells, potentially stopping or even reversing tumor growth. While it is premature to say that CBD cures cancer, it is worth further research.
  • Dravet Syndrome/Epilepsy: In October of 2013, the Food and Drug Administration (FDA) approved two clinical trials assessing the therapeutic uses of CBD in treating intractable epilepsy in children. The CBD preparations are being made by British pharmaceutical company GW Pharmaceuticals, makers of Sativex. Dravet is a rare seizure disorder where usually children will have their first intractable seizure before they are even one year old, and in exceptional cases seizures can last over 24 hours. Harborside, where I work, has a famous patient named Jayden, a young boy who uses a CBD-rich tincture to treat his Dravet Syndrome.
  • Depression/Anxiety: CBD stimulates the 5-HT1a receptor in the brain, a region involved in the re-uptake of serotonin and other processes that aid with depression and anxiety. The antidepressant properties of CBD are very similar to the trycyclic antidepressant Imipramine (also being evaluated for panic disorder).
  • Diabetes: CBD was first discovered to mitigate the effects of diabetes in 2006. since then it has been shown to have numerous benefits for people with diabetes, specifically in reducing neurotoxicity and inflammation. In a follow up study done in 2010, it was found that CBD worked as a defense against neurodegeneration. Another 2010 study said CBD had “great therapeutic potential in the treatment of diabetic complications, and perhaps other cardiovascular disorders.”
  • Inflammatory Bowel Disease/Crohn’s Disease: CBD shows a lot of promise for controlling the inflammatory responses and discomfort caused by Crohn’s disease and IBD. CBD has so much potential to regulate these diseases that it is being considered for a new class of IBD drugs.
  • Nausea: In a study done on nausea and vomiting, CBD was shown to have anti-emetic, anti-nausea effects. The same study found that CBG could block these anti-nausea effects, perhaps because moderate doses of CBD and CBG may oppose eachother at the 5HTP1a receptor in the brain.
  • Schizophrenia/Psychosis: CBD is a powerful antipsychotic currently being considered for use in treating schizophrenia and other psychoses. Cannabidiol appears to have a very similar chemical profile to certain atypical antipsychotic drugs.

  • CBDa

    Cannabidiolic Acid

    CBDA, CBD-acid or CBD-a is the main form in which CBD exists in the cannabis plant, along with THCA (THC-acid). CBD is obtained through non-enzymatic decarboxylation from the acidic form of the cannabinoid, this reaction taking place when the compounds are heated. Heating or catalyzing CBDa transforms it into CBD, thereby increasing the total CBD level. Research shows higher concentrations of CBDA displayed more pronounced antimicrobial activity than CBD alone.

  • Antibacterial – Slows bacterial growth.
  • Anti-Emetic – Reduces vomiting and nausea.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.

  • CBDv

    Cannabidivarin

    CBDA, CBD-acid or CBD-a is the main form in which CBD exists in the cannabis plant, along with THCA (THC-acid). CBD is obtained through non-enzymatic decarboxylation from the acidic form of the cannabinoid, this reaction taking place when the compounds are heated. Heating or catalyzing CBDa transforms it into CBD, thereby increasing the total CBD level. Research shows higher concentrations of CBDA displayed more pronounced antimicrobial activity than CBD alone. Like THCV, CBDV differs from CBD only by the substitution of a pentyl (5 carbon) for a propyl (3 carbon) sidechain. Although research on CBDV is still in its initial stages, recent studies have shown promise for its use in the management of epilepsy. This is due to its action at TRPV1 receptors and modulation of gene expression.


    CBG

    Cannabigerol

    A non-psychoactive cannabinoid, CBG’s antibacterial effects can alter the overall effects of cannabis. CBG is known to kill or slow bacterial growth, reduce inflammation, (particularly in its acidic CBGA form,) inhibit cell growth in tumor/cancer cells, and promote bone growth. It acts as a low-affinity antagonist at the CB1 receptor. CBG pharmacological activity at the CB2 receptor is currently unknown.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-Epileptic – Reduces seizures and convulsions.
  • Anti-Inflammatory – Reduces inflammation systemically.
  • Anti-Insomnia – Aids with sleep.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Bone Stimulant – Promotes bone growth.
  • Neurogenic – CBG is the only cannabinoid identified that helps stimulate the growth of new brain cells.
  • Currently Being Studied For:

  • Glaucoma: A 2009 study found both CBG and THC to be very effective for relieving the intraocular pressure from glaucoma. This is an area that will undoubtedly be receiving more research in the years to come.
  • Inflammatory Bowel Disease: Much like CBD, CBG shows a lot of potential for controlling the inflammation that leads to IBD, and like CBD warrants further research.
  • Painkiller and Anti- Inflammatory: Recent research suggests that CBG has anti-inflammatory and analgesic properties and recommends further study.
  • 5-HT1a Receptor Agonist/Antagonist?: CBG appears to do something at the 5-HT1a receptor that is not fully understood. It modulates the effects of other cannabinoids at this brain site, which is the hub of emotions and depression regulation in the brain. Depending on the study, evidence suggests that CBG may help with depression and anxiety, or possibly block certain anti-depressant drugs. One study in rodents showed that if the right combination of CBG and CBD were present the CBG would block some of the anti-nausea effects of the CBD, but it could not quite identify why (other than it related to the 5HT1a receptor).
  • Dravet Syndrome/Seizures: Anecdotal evidence and some current studies suggest that CBG may be beneficial to patients with Dravet and other seizure conditions. A new tincture was just released at Harborside Health Center which is the first CBG-rich tincture on the market. This tincture, named Jayden’s Juice after Jayden David, the young boy with Dravet syndrome made famous by Weed Wars, is currently what Jayden is using to combat his seizures instead of a purely CBD rich tincture. A study from earlier this year also suggests that CBG may help with seizure management, but the mechanisms aren’t fully understood.

  • CBGa

    Cannabigerolic Acid

    Cannabigerolic acid (CBGa) is formed when geranyl pyrophosphate combines with olivetolic acid within the cannabis plant. It is thanks to CBGa that all other medicinal effects of cannabis are possible. Cannabigerolic acid (CBGa) can be thought of as the stem cell cannabinoid, which becomes THCa/THC, CBDa/CBD, CBCa/CBC, and CBG. It does this through different types of biosynthesis, where chemicals combine to form new compounds, examples being the THC biosynthase and the CBD biosynthase. Hemp strains of cannabis have higher amounts of CBG due to a recessive trait, which may imply higher amounts of CBGa present in those strains as well.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth through apoptosis.

  • CBN

    CBN is a mildly psychoactive cannabinoid that is produced from the degradation of THC. There is usually very little to no CBN in a fresh plant. CBN acts as a weak agonist at both the CB1 and CB2 receptors, with greater affinity for CB2 receptors than CB1. The degradation of THC into CBN is often described as creating a sedative effect, known as a “couch lock.”

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-Emetic – Reduces vomiting and nausea.
  • Anti-Epileptic – Reduces seizures and convulsions.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Insomnia – Aids with sleep.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Appetite Stimulant – CBN appears to be a mild appetite stimulant.
  • Bone Stimulant – Promotes bone growth by stimulating osteocytes.

  • Terpene Profiles:

    Limonene

    Limonene is a cyclic monoterpene that has a pronounced citrus odor and flavor, somewhat sweet yet tangy and bitter. Unsurprisingly, limonene is most commonly found in highest concentrations in the rinds of citrus fruit. Most of the research on the medicinal effects of limonene have focused on d-limonene, rather than other constituents of limonene like perillyl alcohol or a-limonene. A terpene with a wide range of uses, limonene is a commonly used terpene in perfumes, household cleaners, food, and medicines. A major reason for limonene’s widespread use is its very low toxicity. While not being toxic to humans, a recent study done in the United Kingdom shows that allergic reactions to limonene and linalool are more common than previously thought. Limonene is a chemical precursor to the terpenoid Carvone, and may be related to α-pinene. Limonene has numerous medicinal benefits including promoting weight loss, aiding digestion, and preventing gastric distress. It has been shown to be an anti-fungal agent, making it a natural remedy for athlete’s foot or outbreaks of yeast. Limonene also shows promise as a treatment for anxiety and depression. Most interestingly, limonene has been shown both to stimulate the immune system and be an effective treatment for cancer.

  • Antidepressant – Relieves symptoms of depression.
  • Antifungal – Inhibits the growth of fungus.
  • Anti-Inflammatory – Reduces inflammation.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Anxiolytic – Relieves anxiety.
  • Gastro-Oesophageal Reflux – Reduces acid reflux.
  • Immunostimulant – Stimulates the immune system.

  • Eucalyptol

    Eucalyptol has been shown to help with more conditions than most other commonly found terpenes, making it a subject of much research and of great therapeutic value. Cineole can be topically applied to the skin, gums, or other areas. It can also be taken orally by being inhaled, drank as a tincture, or eaten. When taken orally or applied topically it is important to dilute the strength of the essential oil. In high enough doses, like with all chemicals, eucalyptol is toxic and can cause death; unlike the other terpenes and cannabinoids I have covered, at least two people have died from cineole overdose. Fun fact – Eucalyptol has been shown to be anti-fungal, something that prevents or hinders the growth of fungus. Despite that fact, a fungus was recently discovered that produces eucalyptol in large amounts which has potential for use in future biofuels. Analgesic – Relieves pain.

  • Antibacterial – Slows bacterial growth.
  • Anti-Fungal – Inhibits the growth of fungus.
  • Anti-Inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Antioxidant – Prevents the damage of oxidation to other molecules in the body.

  • Linalool

    Up until now of these profiles have focused specifically on cannabinoids; this post will be the first that shifts the focus to the larger discussion of terpenoids and terpenes. Cannabinoids are a class of terpenophenolic compounds, part terpenoid and part phenol. 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 scent. 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 scents and flavors. The different combinations of terpenes and cannabinoids found in cannabis are what give strains their distinct flavors and scents, as well as their medicinal properties. In this first terpene profile we’ll discuss linalool, a common terpene in cannabis although best known for giving lavender its distinct scent and flavor. Linalool is also often used in aromatherapy as a sleep aid, a relaxant and as a treatment for anxiety for thousands of years. Linalool is crucial in the production of Vitamin E in the body, which makes it a very important terpene for healthy functioning. Analgesic – Relieves pain.

  • Antidepressant – Relieves symptoms of depression.
  • Anti-Epileptic – Reduces seizures and convulsions.
  • Anti-Inflammatory – Reduces inflammation.
  • Antipsychotic – Tranquilizing effects relieve symptoms of psychosis.
  • Anxiolytic – Relieves anxiety
  • Sedative – Promotes sleep.

  • Pinene

    Pinene is the main terpene in pine trees which gives them their characteristic scent. It’s a major constituent of turpentine and is also found in high amounts in rosemary and cannabis. Although pinene has two main isomers, alpha– and beta-pinene, alpha-pinene is the dominant one found in cannabis and what I will be referring to when I mention pinene within this article. Pinene is one of the most common terpenes in the plant world and is commonly found in higher concentrations in strains like Jack Herer, Chemdawg, Bubba Kush, Trainwreck, and Super Silver Haze. Pinene is also crucial to our bodies because it forms the biosynthetic base for CB2 ligands in the endocannabinoid system. Evidence shows that pinene can be a bronchodilator, increasing airflow to the lungs and helping with conditions such as asthma. Like many terpenes and cannabinoids, pinene is both an analgesic and anti-inflammatory, making it useful for a sufferer of chronic pain. Pinene helps fight cancer by encouraging apoptosis and being an anti-proliferative. Pinene is an antioxidant and even appears to aid in memory retention.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Antioxidant – Prevents oxidation damage to other molecules in the body.

  • Caryophyllene

    Caryophyllene is the primary terpene that contributes to the spiciness of black pepper and also a major terpene in cloves, hops, rosemary, and cannabis. It comes in two main forms, beta caryophyllene, also commonly seen as β-Caryophyllene or abbreviated to BCP, and trans-caryophyllene or TC. While this article primarilly looks at BCP, a couple studies do concern TC, and I will use caryophyllene generically throughout. Caryophyllene is a sesquiterpene, made of three isoprene units, which makes it larger than monoterpenes like pinene, limonene and myrcene, which are made up of only two isoprene units. What makes caryophyllene chemically unique is its inclusion of a cyclobutane ring, which is a rarity in nature and makes it an attractive candidate for biotech research. Some cyclobutanes have already found medical uses, such as the chemotherapy drug Carboplatin. As BCP has also been shown to have cancer fighting properties it could be viable candidate for a new chemotherapy drug. Caryophyllene isn’t only unique for being a cyclobutane, it is unique for being both a terpene and a “dietary cannabinoid,” a food-stuff which acts as a cannabinoid and binds to CB2 receptors. As stated in my first terpene profile, cannabinoids are a terpenophenolic compound, sub-set of terpenes. Since cannabinoids and terpenes are related it is no surprise that terpenes would trigger the body’s endo-cannabinoid receptors. The same 2008 study, which first identified caryophyllene as a cannabinoid, also found it had numerous medicinal benefits, including anti-oxidant, anti-inflammatory, anti-cancerous and local anesthetic effects. Some sources speculate that BCP is so powerful it could threaten existing pharmaceuticals, and synthetic cannabinoids currently being developed, which could be why BCP is so heavily studied.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Antidepressant – Relieves symptoms of depression.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Antioxidant – Prevents oxidation damage to other molecules in the body.
  • Anxiolitic – Helps relieve anxiety.
  • Neuroprotective – Slows damage to the nervous system and brain.

  • Terpinolene

    Terpinolene has a smokey or woody odor and is found in apple, cumin, lilac and tea tree. Terpinolene is also known as δ-terpinene, or delta terpinene. All terpinenes have the same molecular formula, weight and framework, but they differ in the placement of the carbon-carbon double bonds. Terpinolene is neither an analgesic or an anti-inflammatory, which is surprising as most cannabinoids and terpenoids are one of the two, if not both. It does help fight cancer like most other cannabinoids, and it is anti-fungal as well as anti-bacterial. Terpinolene is a sedative which may also be helpful in cancer treatment if patients have difficulty sleeping, possibly in conjunction with other terpenes or cannabinoids like linalool and cannabinol, Outside of the human body, terpinolene has been shown to be an effective natural method to repel both mosquitoes and weevils.

  • Antibacterial – Slows bacterial growth.
  • Anti-Fungal – Inhibits the growth of fungus.
  • Anti-Insomnia – Aids with sleep.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Antioxidant – Prevents oxidation damage to other molecules in the body.

  • Humulene

    Humulene is one of the predominant terpenes in Humulus Lupulus, common hops, from which it gets its name; it’s also found in cannabis, sage, and ginseng. Humulene is also commonly called α-humulene or α-caryophyllene. While humulene is related to β-caryophyllene it is a different isomer with distinct properties, and it has yet to be recognized as a dietary cannabinoid. Like caryophyllene, humulene is a sesquiterpene made of three isoprene units, but it does not contain a cyclobutane ring. Humulene is like most other cannabinoids and terpenes in that it is a powerful anti-inflammatory and an analgesic. It also displays anti-cancer properties. Humulene is unique because, like THCv, it acts as an appetite suppressant, making it promising for weight loss treatments.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Proliferative – Inhibits cancer cell growth.
  • Anorectic – Appetite suppressant, promotes weight loss.

  • Borneol

    Borneol will be the last terpene I profile for this series, rounding out my coverage on all the major cannabinoids and terpenes. Borneol is also commonly known as natural borneol and formerly known as Borneo Camphor. Borneol is described as having a minty, spicy, cooling, or herbal scent and it is found in high concentrations in camphor, rosemary, and mint plants. Borneol is a bicyclic monoterpene, composed of two isoprene rings fused together; this makes it larger than monoterpenes like limonene yet smaller than sesquiterpenes like caryophyllene. Chinese traditional medicine has used borneol as a moxa for acupuncture, topically, and orally, since at least the writing of the Compendium of Materia Medica in the late 1600s, but likely for much longer. The first mention of borneol by western doctors was in 1888 by Dr. Ralph Stockman, who conducted the first documented experiments on it at Edinburgh University. In addition to numerous medicinal properties, borneol also is a natural insect repellent, preventing disease being passed by mosquitoes, fleas and other pests. Research released on January 8th shows that borneol can be an effective disease vector control method to combat West Nile and other mosquito borne pathogens.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth
  • .
  • Anti-Fibrosis – Balances the body’s fibrosis response to injury.
  • Anti-Fungal – Inhibits the growth of fungus.
  • Anti-Inflammatory – Reduces inflammation systemically.
  • Antioxidant – Prevents oxidation damage to other molecules in the body.

  • Myrcene

    Myrcene is a monoterpene, the smallest of the terpenes, it is found in very high concentrations in sweet basil, hops, mangoes and cannabis. Myrcene is described as possessing an earthy, fruity clove-like odor, but can be very pungent in higher concentrations, as in heavily hopped beers. Not surprisingly, hops and cannabis are cousins, both members of the family Cannabaceae. Myrcene gets its name from Myrcia sphaerocarpa, a medicinal shrub from Brazil that contains very high amounts of myrcene which has been used there for ages as a folk remedy for diabetes, dysentery, diarrhea, and hypertension. A 1997 study conducted in Switzerland analyzed various cannabis strains for 16 terpenes and found myrcene to be the most abundant terpene out of those studied (others include Pinene, Limonene, Carene, Humulene, Bergamotene, Terpinolene, and Caryophyllene). For some strains, the myrcene content can be over half the total terpene content. Myrcene is crucial in the formation of other terpenes and it synergizes the antibiotic potential of other terpenes. One reason why myrcene could be so commonly found in cannabis is that it has been shown to change the permeability of cell membranes to allow more absorption of cannabinoids by the brain. This effect of myrcene has been known about since the 1970s and long ago spawned a rumor that eating a ripe mango before smoking would get you higher. According to recent information published by Steep Hill Labs, a major cannabis testing laboratory in the Bay Area, for most people eating a fresh mango 45 minutes before inhaling cannabis will increase the effects of that cannabis. Rev. Dr. Kymron de Cesare of Steep Hill is an advocate of what he calls “overlapping synergies” between myrcene and other terpenes with the various cannabinoids, such as how myrcene makes THC more effective.

  • Analgesic – Relieves pain.
  • Antibacterial – Slows bacterial growth.
  • Anti-Diabetic – Helps mitigate the effects of diabetes.
  • Anti-inflammatory – Reduces inflammation systemically.
  • Anti-Insomnia – Aids with sleep.
  • Anti-Proliferative/Anti-Mutagenic – Inhibits cell mutation, including cancer cells.
  • Antipsychotic – Tranquilizing effects relieve symptoms of psychosis.
  • Antispasmodic – Suppresses muscle spasms.

  • Hashishene

    The November 2014 Journal of Chromatography featured a study entitled “Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L.” While unfortunately this study has nothing to do with traveling to other dimensions, it has some very interesting findings for anyone making dry sieve hash, potentially other forms of hash, and perhaps other plant concentrates as well. The researchers analyzed numerous samples of hashish, a total of “15g of hashish (probably originating from Morocco).” Analysis was made using various techniques including “headspace solid phase microextraction (HS-SPME) and gas chromatography techniques (GC-MS, GC×GC-MS).” Before we go any further, lets talk about how the researchers define hashish. For this study, hashish is a concentrated form of cannabis “produced via a relatively long cottage industry process that consists in successively drying, sieving, and finally pressing the resin-rich buds of cannabis plants that have been harvested at full blooming stage. It results in a medium hard greenish-brownish paste that softens upon heating.” That means these researchers were looking at hashes that were not decarboxylated by anything more than body heat, unlike rosin. They also were not looking at chemical-extracted hashes, like CO2 oils, BHO, or iso hash. Looking at their samples, the researchers found they could tell which samples were dried herb from those that were hashish, because hash contained “remarkable amounts of a rare and unusual monoterpene 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane [1.1 to 14.9% (median value: 10.2 %)].” The researchers were “rather surprising to find [it] in such high abundance among the volatile constituents of hashish samples since the natural occurrence of this compound was reported only once in the past as a minor constituent (< 0.1%) of the essential oil of Mentha cardiaca L [Scotch Spearmint Oil].” Due to its high abundance in hash and relative scarcity elsewhere, the researchers have proposed renaming it hashishene. You may now be wondering, how exactly is this new terpene formed? Hashishene was found to be created by the “light induced rearrangement of β-myrcene during the manufacture of hashish.” In other words, hashishene is a somewhat-degraded form of myrcene; which is why it has the same molecular weight and formula as myrcene, though a radically different chemical structure. The researchers suspect that because “hashish is manufactured according to a lengthy process involving repetitive steps of sieving and drying of the resin-rich female heads of cannabis plants” there is plenty of opportunity for “exposure to sunlight during those drying steps [which] could therefore be reasonably considered responsible for the photolytic formation of [hashishene] from [myrcene].”
    The use of hashishene as a way to detect hash samples has clear value to law enforcement and other government and research groups, as a result the researchers have already submitted “the use of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as volatile marker of hashish” to the European Union for patent protection. But, since hashishene has already been found in at least one other plant, Scotch Spearmint, perhaps use of this method will result in false positives. Since hashishene is a mutated form of myrcene, and myrcene exists widely in nature, in fruit like mangoes and herbs like hops, then theoretically hashishene should exist in other concentrated forms of plants, such as heavily hopped beer or potentially in essential oils used in aromatherapy. Investigating other concentrates, like heavily-hopped beers, could make for interesting follow-up research. Little is known about hashishene, including its medical properties, that will also take further study to know more.


    Flavonoids:

    WHAT ARE FLAVONOIDS?

    The unique smell and flavor of a cannabis strain is produced in part by its flavonoids, the aromatic molecules. Some flavonoids, like quercetin, luteolin and kaempferol, naturally appear in many different plants. But flavonoids that are unique to cannabis are called CANNAFLAVINS, and they don’t just smell good, they are pharmacologically active. For example, cannaflavin A has been found to to reduce inflammation by inhibiting the inflammatory molecule PGE-2, and it does this 30 times more effectively than aspirin. Similar to CBD, flavonoids also modulate the effects of THC. Through complex biochemical mechanisms, flavonoids interact on many different sites in the body. Some interact with estrogen receptors, others act as potent antioxidants or inhibit enzymatic processes.

    Flavonoids are secondary polyphenolic metabolites that commonly have a ketone group and yellowish pigments, after which they are named (from the Latin flavus, “yellow”). Flavonoids can be divided in four main groups: flavonoids, isoflavonoids, neoflavonoids and anthocyanins. Nevertheless, for the sake of simplicity, we will refer to them all with the common term of flavonoids.

    Carnivorous plants as the Dionaea muscipula contain a type of flavonoid in their flowers and leaves that attracts the insects they will eat. Flavonoid biosynthesis follows the phenylpropane metabolic pathway, in which the cumaril-SCoA is formed from the aminoacid known as phenylalanine, which is mixed together with the malonil-CoA form a group of substances known as chalcones. These are the backbone of every flavonoid and anthocyanin's biosynthesis. This reaction is catalysed by the chalcone synthase enzyme, which belongs to the family of the polyketide synthases (PKS). This PKS family also contains olivetol synthase, responsible for the synthesis of cannabinoids. Flavonoids cover a wide range of functions in plants, although they mainly act as yellow pigments in petals and leaves to attract pollinating insects. They might also appear as bluish pigments (anthocyanins) to receive certain wavelengths of light, which permits the plant to be aware of the photoperiod. Many of these flavonoids also protect the plant by being involved in the filtering of ultraviolet light. On a cellular level, flavonoids act as regulators of the cellular cycle. Some of them are synthesised in the plant's roots and have crucial roles in establishing symbiotic fungi or mycorrhyzas, while at the same time they fight the infections caused by pathogenic fungi. Flavonoids have relevant pharmacological activities on 'in vitro' models, such as; antioxidant, anti-inflammatory, antiallergic, antibiotic, antidiarrheal and against cancer. It has not been possible to prove an antioxidant activity on 'in vivo' models, just as it has not been possible to relate it to any effectiveness against cancer. Some studies seem to indicate that a diet rich in flavonoids can diminish the risk of cancer, but there are no significant statistics regarding this claim. We can find different types of flavonoids in the Cannabis plant, such as; cannflavine A, cannflavine B, cannflavine C, vitexin, isovitexin, apigenin, kaempferol, quercetin, luteolin and orientin. The distribution of these in the plant, varies depending on the type of flavonoid, but none have been found in the root system of the Cannabis plant. The total content of flavonoids in the Cannabis' leaves and flowers can reach 2,5% of its dry weight, while it is almost non existent in seeds and roots. Some studies suggest that the distribution and concentration of flavonoids in the Cannabis plant can be useful from a chemical and taxonomic point of view. The following is a brief description on the therapeutic properties of these flavonoids. Most of these compounds are soluble in water, which could explain certain therapeutic effects of the herbal infusions and the decoctions in Cannabis water, as the cannabinoids are partly soluble in water.