Terpenes

Set of molecules that interact with the receptors of the Endocannabinoid System

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Terpenes and their importance in medical cannabis

With the advancing research on the cannabis plant and its therapeutic uses, more and more active components present in the plant have been found, however, their functions have not been studied enough. Several studies have shown that at the same dose of cannabinoids, the effects produced by the administration of pure cannabinoids are different from those produced by the administration of whole plant extracts. These facts lead us to the conclusion that the cannabis plant contains other active ingredients that have pharmacological action, and that act synergically and/or antagonistically with cannabinoids. The two groups found so far are terpenes and flavonoids.

Terpenes are volatile compounds that become part of atmospheric gases, but they can also accumulate inside plants.

The wide variety of medicinal properties in these compounds opens up unsuspected development opportunities for scientific research. As research progresses, the complexity of terpene functions and their benefits are discovered.

What are terpenes?

Terpenes are aromatic organic compounds derived from isoprene (hydrocarbon 5 carbon atoms), they are found in all kinds of vegetation and are important in numerous biotic interactions (Goodwin 1971). They exercise primary functions such as protection against various factors like high temperatures, insects or herbivore predators. They have also been found as part of chlorophyll and some carotenoid pigments.

The functions of terpenes at the plant level are varied and are responsible for highly specialised processes that allow plants to have a protection against the elements around it. Among its functions are the colouring, repellent or aromatization that facilitates the pollination of the plants.

Effects of terpenes

Like cannabinoids, terpenes have various effects on humans. Known as essential oils, they are currently used in aromatherapy. Aromatherapy brings together several concepts that, at a therapeutic level, have been attributed to various plants. It offers the idea that when used properly these plants can have relaxing, stimulating of aphrodisiac effects on people.

The terpenes present in the cannabis plant are responsible for the range of aromas that exist between the different varieties, however, it is estimated that they are not the only effects that can be attributed. They seem to have a link in relation to the entourage effect.

Benefits of terpenes

  • Antiseotuc
  • Antifungal
  • Anti-inflamatory
  • Anti-bacterial
  • Anxiety
  • Anti-depression
  • Bronchodilator

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Terpenes in cannabis

The terpenes in the cannabis plant are excreted in the resin. It is thanks to them that there are different types of plants, each with their own unique odours, because this variation is dependent on the terpenes that are present. The terpenes in the cannabis plant allow it to protect itself against high temperatures and due to the viscosity of the resin, the plant can trap insects or maintain its own humidity.

Between the terpenes we can find in big amount within the cannabis there are: Pinene, Myrcene, Limonene, Linalool and Eucalyptol. Following we can also find the Caryophyllene, which is present in every cannabis strain.

El olor y sabor del cannabis y de muchos otros productos depende de la presencia y la proporción de los diferentes terpenos que encontramos en las plantas aromáticas.

Además de los cannabinoides, existen otros compuestos químicos con potencial terapéutico en la planta. Destacan especialmente los Terpenoides, a los que se atribuye parte de las propiedades organolépticas del Cannabis (McPartland y cols., 2014).

Terpenes in cannabis | Kalapa Clinic

Myrcene

Myrcene, or beta-myrcene, is one of the most abundant terpenes in nature, being present in hops, thyme and myrcia among others. It is known to have a sedative effect and therefore is used to reconcile sleep. In cannabis plants, it is mainly present in the Indica varieties and can potentiate the psychoactive effect of THC.

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Main therapeutic effects of myrcene:

  • Sedative, hypnotic and muscle relaxing effects
  • Analgesic effect
  • Anti-Inflammatory effect
  • Antibiotic effect
  • Antitumor effect
  • Antispasmodic effect

Pinene

The name pinene refers to two bicyclic monoterpenes isomers, alpha-pinene and beta-pinene. Present mainly in pine and other conifers, it is one of the terpenes that are also widely present in nature. Its bronchodilator activity facilitates the absorption of cannabinoids at the pulmonary level.

Main therapeutic effects of pinene:

  • Antibacterial and antifungal effects
  • Anti-inflammatory effect
  • Bronchodilator effect

Limonene

Limonene is present especially in the skin of lemons and other citrus fruits. In addition to its own therapeutic effects, it facilitates the absorption of other terpenes thus enhancing its effects. Recent studies indicate that it promotes the GST system of the liver and intestines, mitigating the carcinogenic effects.

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Main therapeutic effects of limonene:

  • Antibacterial and antifungal effects (especially against Aspergillus)
  • Antitumor effect
  • Antidepressant and anxiolytic effects
  • Bronchodilator effect

Eucalyptus

Eucalyptus is a monoterpene present mostly in the leaves of the eucalyptus tree. In the cannabis plant it is mainly present in the sativa strains. It is the only terpene that has shown some activity on the Central Nervous System.

Eucalptus

Main therapeutic effects of eucalyptus:

  • Immunosuppressant effect
  • Local anaesthetic effect

Caryophyllene

When talking about Caryophyllene we refer to the mixture of 3 compounds: alpha-caryophyllene, beta-caryophyllene and caryophyllene oxide. All these components are present in the cannabis plant with caryophyllene oxide being the chemical substance police dogs are trained to detect when trying to find cannabis. Besides cannabis they are also present in hops, cloves and black pepper, among others. As this terpene is less volatile, compared to the others, it is found in larger proportions in cannabis extracts.

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Main therapeutic effects of Caryophyllene:

  • Antibacterial and antifungal effects
  • Antitumoral effect
  • Anti-inflammatory effect

Beta-caryophyllene

Beta-Caryophyllene, also known as BCP, is a terpene that is present in a wide variety of essential oils. BCP especially affects CB2 cannabinoid receptors, which can be called cannabinoid mimetic. [4] This is because the CB2 receptor generates a biological response to its presence, as is the case with cannabinoids. Much like the cannabinoids that act on CB2 receptors, it is being investigated whether this terpene has analgesic effects and works in inflammatory processes or in cases of neuropathic pain[5]

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Main therapeutic effects of Beta-caryophyllene

  • Analgesic
  • Anti-Inflammatory

The terpene entourage effect

The presence of such a high quantity of different compounds in the cannabis plant can lead to pharmacological interactions, either synergistically or antagonistically. Studying these interactions has shown that, both in terms of efficacy and tolerability, treatments with whole plant preparations have been more promising than the use of isolated cannabinoids. This effect, called the “entourage” effect, was first described by Raphael Mechoulam in 1998 (Ben-Shabat, 1998; Russo and Taming, 2011). The best example described so far is the THC-CBD couple whose combination makes THC better distributed, increases bioavailability (our body uses the available amount in the most efficient way) and reduces possible side effects (McPartland et al, 2014). Although there are few studies on the subject, it is believed that the entourage effect is not only due to interactions between different phytocannabinoids, but also to the functional interaction between cannabinoids and noncannabinoid plant components such as terpenes and flavonoids.

If terpenes are combined with cannabinoids, the effects of the latter can be more powerful. Two essential oils composed mainly of limonene have been shown to inhibit the bacteria Propionibacterium acnes, the key pathogen that causes acne, more effectively than triclosan. Similarly, linalool demonstrated a complementary anti-inflammatory effect, while pinene was the most powerful component of the tea tree and eucalyptus in suppressing acne-producing bacteria.

Some studies have also focused on the ability of terpenes to combat methicillin-resistant staphylococcal (MRSA) infections. This is a strain of Staphylococcus aureus bacteria that is resistant to different antibiotics. Pineapple has been shown to be effective in fighting this type of infection and other bacteria that are resistant to antibiotics. In addition, the ability of terpenes to improve skin permeability and the entry of other drugs can further enhance antibiotic benefits.

It was the lack of information on the entourage effect that led Dr Ethan Russo of the University of Massachusetts to publish an essay on the synergy of phytocannabinoids and terpenes in 2011.

Similarly, these two terpenes and pinene may help to increase the effect of THC on dementia in Alzheimer’s patients. Linalool, together with caryophyllene and myrcene, can increase the effects of several cannabinoids on sleep problems. Finally, caryophyllene, myrcene and pinene may be useful in providing adjuvant support in treating addictions

Four basic synergy mechanisms have recently been proposed (Wagner and Ulrich-Merzenich, 2009):

Multi-target effects
Pharmacokinetic effects such as improved solubility or bioavailability
Interactions of agents affecting bacterial resistance
Modulation of the adverse effects that can be achieved by the entourage

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References for Terpenes

[1] Goodwin, T.W. 1971. Aspects of terpenoid chemistry and biochemistry. Academic Press, Londres

[2] Estudio de las emisiones de terpenos por la especie nativa schinus molle l. (pimiento), sus variaciones temporales y su contribución al mejoramiento del inventario de emisiones de la región metropolitana

[3] Mónica Polo, Rosana Crespo, Marianela Galle, Boris Rodenak Kladniev, Sandra Montero Villegas, Margarita García de Bravo Actividades antiprofilerativa y anticolesterogénica de estatinas y monoterpenos.   Acta bioquím. clín. latinoam. vol.47 no.2 La Plata abr./jun. 2013

[4] http://www.pnas.org/content/105/26/9099.long

[5] A.-L. Klauke1, I. Racz, B. Pradier, A. Markert, A.M. Zimmer, J. Gertsch, A. Zimmer. The cannabinoid CB2 receptor-selective phytocannabinoid beta-caryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain  April 2014 Volume 24, Issue 4, Pages 608–620

Imágenes moléculas por Ben Mills and Jynto – Derivative of File:(R)-(−)-carvone-from-xtal-3D-balls-A.png and File:Diketene-from-xtal-3D-balls.png., Public Domain, https://commons.wikimedia.org/w/index.php

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