Terpene Profile: β-Caryophyllene

By Mitchell Colbert

This post first appeared on The Leaf Online, October 21st, 2014.

Caryophyllene-The-Leaf-Online

Formula: C15H24

Molecular Mass: 204.35106 g/mol

Boiling Point: 160 °C (320 °F)

Vapor Pressure: 0.01 mmHg ( 25 °C)

LD50 (Lethal Dose): >5g/kg for rats (Compare to Nicotine: for mice – 3mg/kg for humans – 40–60 mg/kg)

 

Last week I profiled the main cannabinoid present in dried cannabis, THC. This week I will profile one of the major terpenes present in Cannabis, caryophyllene. Before we get to the profile itself, let's have a brief organic chemistry lesson to better understand how cannabinoids and terpenes interact with eachother. Cannabinoids are a class of terpenophenolic compounds, part terpenoid and part phenol. All phenols are aromatic hydrocarbons, which means they have a very pronounced scent. Terpenes, on the other hand, are hydrocarbon groups created by various combinations of the isoprene units that make them up, and may be aromatic.  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. 

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. Cannabinoids are a terpenophenolic compound, which is 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 sourcesspeculate 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.

 

Beta-Caryophyllene

 

Therapeutic Uses

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.

Currently Being Studied For

Longevity: A study released just last month shows, for the first time, that BCP can make you live longer; at least in the case of the nematode Caenorhabditis elegans. This small worm has been studied for years, because scientists can use it to model how things will affect humans. This breaking study shows that BCP’s abilities to reduce stress are powerful enough to increase the lifespan of worms and potentially humans.

Maybe a treatment for alcohol abuse: Perhaps the reason caryophyllene led to a longer lifespan is because it helps you stop drinking, maybe not in the case of worms but possibly for humans. This 2014 study discovered that BCP reduced voluntary intake of alcohol by mice and recommended using it for treatment of alcoholism.

Analgesic: Like most cannabinoids and many terpenes, BCP is an analgesic, specially a local anaesthetic. More recent research shows that BCP is “highly effective in the treatment of long lasting, debilitating pain states,” and recommends its use as a dietary aid for chronic pain.

Antioxidant: Research shows that caryophyllene is an antioxidant. Antioxidants are free radical scavengers that roam the body getting rid of damaging free radicals. According to some sources, antioxidants like BCP, may help slow down the effects of aging and promote a longer life. Recent research using Caenorhabditis elegans may have debunked the theory that antioxidants increase your lifespan, but caryophyllene still may.

Anti-Inflammatory: BCP is a powerful anti-inflammatory with “tremendous therapeutic potential in a multitude of diseases.” Trans-caryophyllene has been shown to reduce inflammation in the brain caused by hypoxia. In various forms, caryophyllene joins a host of other terpenes and cannabinoids in being an anti-inflammatory.

Anxiety and Depression: study released in august found BCP relieves the symptoms of anxiety and depression, and suggests further study into how it can be used to treat these conditions. Like many studies on caryophyllene, this is exploratory research and needs further study to back up its findings.

Cancer: This 2007 study found that BCP increased the effectiveness of the chemotherapy drugPaclitaxel. A 2014 study found that BCP had anti-cancer properties of its own, by stimulating apoptosis and by suppressing tumor growth.

Diabetes: Lipid dysregulation is one of the many complex factors that fit together to lead to someone developing diabetes. A 2013 study shows that caryophyllene assists with the regulation of lipids and may thus help mitigate the effects of, or delay the onset of, diabetes.

Inflammatory Bowel Disease: Caryophyllene helps with inflammation throughout the body, including the bowels. A 2011 study found it to be an extremely effective a treatment for Inflammatory Bowel Disease.

Neuro-Inflammation/Brian Ischemia:  As we already read, trans-caryophyllene helps with neuro-inflammation by reducing hypoxia. This builds off a study from 2012 which showed TC reduced the risk of cerebral ischemia, a similar issue where there is a lack of oxygen to the brain.

All phenols are aromatic hydrocarbons, which means they have a very pronounced scent. Terpenes, on the other hand, are hydrocarbon groups created by various combinations of the isoprene units that make them up, and may be aromatic.  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. 

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. Cannabinoids are a terpenophenolic compound, which is 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 sourcesspeculate 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.

 

Beta-Caryophyllene

 

Therapeutic Uses

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.

Currently Being Studied For

Longevity: A study released just last month shows, for the first time, that BCP can make you live longer; at least in the case of the nematode Caenorhabditis elegans. This small worm has beenstudied for years, because scientists can use it to model how things will affect humans. This breaking study shows that BCP’s abilities to reduce stress are powerful enough to increase the lifespan of worms and potentially humans.

Maybe a treatment for alcohol abuse: Perhaps the reason caryophyllene led to a longer lifespan is because it helps you stop drinking, maybe not in the case of worms but possibly for humans. This 2014 study discovered that BCP reduced voluntary intake of alcohol by mice and recommended using it for treatment of alcoholism.

Analgesic: Like most cannabinoids and many terpenes, BCP is an analgesic, specially a local anaesthetic. More recent research shows that BCP is “highly effective in the treatment of long lasting, debilitating pain states,” and recommends its use as a dietary aid for chronic pain.

Antioxidant:Research shows that caryophyllene is an antioxidant. Antioxidants are free radical scavengers that roam the body getting rid of damaging free radicals. According to some sources, antioxidants like BCP, may help slow down the effects of aging and promote a longer life. Recent research using Caenorhabditis elegans may have debunked the theory that antioxidants increase your lifespan, but caryophyllene still may.

Anti-Inflammatory: BCP is a powerful anti-inflammatory with “tremendous therapeutic potential in a multitude of diseases.” Trans-caryophyllene has been shown to reduce inflammation in the brain caused by hypoxia. In various forms, caryophyllene joins a host of other terpenes and cannabinoids in being an anti-inflammatory.

Anxiety and Depression: study released in august found BCP relieves the symptoms of anxiety and depression, and suggests further study into how it can be used to treat these conditions. Like many studies on caryophyllene, this is exploratory research and needs further study to back up its findings.

Cancer: This 2007 study found that BCP increased the effectiveness of the chemotherapy drugPaclitaxel. A 2014 study found that BCP had anti-cancer properties of its own, by stimulating apoptosis and by suppressing tumor growth.

Diabetes:Lipid dysregulation is one of the many complex factors that fit together to lead to someone developing diabetes. A 2013 study shows that caryophyllene assists with the regulation of lipids and may thus help mitigate the effects of, or delay the onset of, diabetes.

Inflammatory Bowel Disease: Caryophyllene helps with inflammation throughout the body, including the bowels. A 2011 study found it to be an extremely effective a treatment for Inflammatory Bowel Disease.

Neuro-Inflammation/Brian Ischemia:  As we already read, trans-caryophyllene helps with neuro-inflammation by reducing hypoxia. This builds off a study from 2012 which showed TC reduced the risk of cerebral ischemia, a similar issue where there is a lack of oxygen to the brain.

Thispost first appeared on The Leaf Online, October 21st, 2014.

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