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β-Caryophyllene|Agonist and Antagonist drugs|beta caryophyllene model|beta caryophyllene diagram on leaf|

Terpenes

Terpene Science: β-Caryophyllene

Today's article is about one of the most common, most famous, most studied and potentially most beneficial of the 30,000 terpenes in the plant world. This is β -Caryophyllene (pronounced "beta-carry-off-ill-een" and frequently written as beta-caryophyllene). Studies have shown this compound to have numerous potential health benefits, including:

    • Anxiolytic (lowers anxiety)

    • Anti-depressant

    • Anti-inflammatory

    • Anti-cancer, enhancing apoptosis (cell death)

    • Neuro-protective (protects against permanent neurological damage when taken after injury)

    • Anti-nociceptive (lowers the experience of pain)

    • Anti-alcoholism (lowers desire for alcohol)

    • Anti-smoking (lowers desire for tobacco)


Many of these studies used rats and other non-human animals as the subjects. However, the evidence is rather clear that β -Caryophyllene can be extraordinarily beneficial in a number of ways.

What it is:


The first synthesis of β- Caryophyllene was in 1964. It is a bicyclic sesquiterpene, which means it contains two rings and consists of three connected isoprene units with a molecular formula of C15H24 (15 carbon atoms and 24 hydrogen atoms). Isoprene is the basic building block of all terpenes and has a basic formula of C5H8 (5 carbon atoms and 8 hydrogen atoms). The compound's molecular weight is 204.35 atomic mass units.  width=

Here is a visualization of the structure of β- Caryophyllene - each black sphere is a carbon atom and each gray sphere is a hydrogen atom.

How it Works:


β- Caryophyllene is a CB2 receptor agonist. CB2 receptors are a type of cannabinoid receptor that appears in various parts of the body including our immune system, gastrointestinal system, brain, and peripheral nervous system.

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You can think of a receptor like a lock, for which an antagonist is a key with a specific shape that fits exactly in that lock and blocks anything else from entering. An agonist is more like a bobby pin or lockpick - a compound with a more generic shape that fits in the lock but could also fit other locks (and multiple different agonists can fit into the same receptor).



By this model, β- Caryophyllene activates the CB2 receptor to produce any or all of the physiological effects listed above. Unlike cannabis-derived cannabinoids which also activate CB2 receptors, β- Caryophyllene has not been found to produce psychoactive effects.

β-Caryophyllene Uses:


β -Caryophyllene is an FDA approved food additive and is found widely in the plant world, including black pepper, cloves, basil, lavender, cinnamon leaves, copaiba, rosemary, and hops. It lends both flavor and spiciness to food, chewing gum, soaps, and detergents.



Additional Information:


Below are some references in case you are interested in finding out more about β -Caryophyllene:

β-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice.

Functionalization of β-caryophyllene generates novel polypharmacology in the endocannabinoid system.

Trans-caryophyllene suppresses hypoxia-induced neuroinflammatory responses by inhibiting NF-κB activation in microglia.

The cannabinoid receptor 2 agonist, β-caryophyllene, reduced voluntary alcohol intake and attenuated ethanol-induced place preference and sensitivity in mice.

The cannabinoid CB₂ receptor-selective phytocannabinoid beta-caryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain.

The antioxidant effect of β-caryophyllene protects rat liver from carbon tetrachloride-induced fibrosis by inhibiting hepatic stellate cell activation.

β-Caryophyllene oxide potentiates TNFα-induced apoptosis and inhibits invasion through down-modulation of NF-κB-regulated gene products.

Beta-caryophyllene and caryophyllene oxide, isolated from Aegle marmelos, as the potent anti-inflammatory agents against lymphoma and neuroblastoma cells.

β-Caryophyllene inhibits dextran sulfate sodium-induced colitis in mice through CB2 receptor activation and PPARγ pathway.

Activation of type 2 cannabinoid receptors (CB2R) promotes fatty acid oxidation through the SIRT1/PGC-1α pathway

Wikipedia: Caryophyllene

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