Cannabinoids and terpenes

What is caryophyllene?

• Name: Caryophyllene, β-Caryophyllene
• Formula: C15H24
• IUPAC name: 4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene
• Molecular mass: 204.36 g/mol
• Boiling point: 130°C (403K)
• Vaporization temperature: 199ºC

First synthesized in the laboratory in 1964 by EJ Corey, caryophyllene (also called β-caryophyllene) is a bicyclic sesquiterpene found in various plants, including basil, thyme, rosemary, oregano, hops, pepper, and, of course, also in cannabis. It is known for its anti-inflammatory and antioxidant properties, and research has been focusing on it in relation to various health benefits.

In fact, caryophyllene is one of the most common terpenes found in marijuana, along with other terpenes like limonene, linalool, and pinene. As you probably already know, terpenes are volatile compounds found in the trichome glands of cannabis, responsible for the aroma and flavor of the plant. Let's delve a little into the properties and effects of this interesting compound!

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As you probably know, THC or tetrahydrocannabinol is the main psychoactive substance present in cannabis. Yes, among the more than 100 phytocannabinoids identified in this plant, THC is, by far, the one with the greatest presence as a psychotropic component. Although this compound has a series of more than interesting medicinal properties, its medicinal aspect has always been in the shadow of its psychoactive capacity, a capacity that historically has not exactly played in its favor in legislative matters.

However, THC has different types called isomers or analogs; For example, the THC we usually talk about is the isomer called Delta-9 THC, although other similar names may sound familiar to you, such as Delta-8 THC or Delta-10 THC, even THCV or THCP. In this article, we are going to talk about the main types of THC that you can find in your cannabis and see its main characteristics and effects.

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What is HHC or hexahydrocannabinol?

• Name: Hexahydrocannabinol
• Formula: C21H32O2
• IUPAC name: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
• Molecular mass: 316.485 g·mol−1
• Melting point: 560.44K
• Boiling point: 837.1K

Recently, a new cannabinoid that until recently had not been heard of has started making headlines in the cannabis press. This is HHC or hexahydrocannabinol, a compound with properties similar to those of Delta-9 THC and Delta-8 THC that is seeing its popularity skyrocket thanks precisely to the effect it causes, which is somewhat softer than that of its THC analogue.

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The endocannabinoid system (ECS) is an intercellular communication system that is made up of endogenous cannabinoid receptors and endocannabinoids (those produced by our own body) and that can also interact with the cannabinoids produced by the cannabis plant (phytocannabinoids).

Cannabinoid receptors are located mostly in the brain and spinal cord (central nervous system), the peripheral nervous system, and in many tissues and organs in our body. These receptors are activated when stimulated by endocannabinoids: their ligands. These molecules fit perfectly with them and allow them to send cellular signals to regulate all kinds of functions in our body. In a similar way, these receptors "listen" to conditions outside the cell and transmit information about those changing conditions to the interior of the cell, initiating the appropriate response.

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Cannabis flowers are consumed for medicinal and recreational purposes based on the properties of their specialised metabolites (such as cannabinoids and terpenes). The metabolites are abundantly produced within the glandular trichomes of the female flowers, which represent the essence of the prized cannabis bud. But despite the economic and medicinal importance of cannabis glandular trichomes, the relative properties and contributions of the different types of trichomes remain poorly understood.

The term trichome comes from the Greek ('thrix', 'trichos', hair or hair) and in many plant species, they form a small hairy covating. Trichome shape ranges from straight or spiral, to globular, which are those that have the greatest interest in cannabis. Trichomes perform various defensive and protective functions, and can be quite specialised; for example, the hair-like cells in carnivorous plants that trigger the trap to close on an unsuspecting insect are derived from trichomes.

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What is Linalool?

• Name: Linalool
• Formula: C10H18O
• IUPAC name: 2,6-dimetil-2,7-octadien-6-ol
• Molar mass: 154.25 g/mol
• Melting point: -20 °C (253.15 K)
• Boiling point: 198.6 °C (471.75 K)
• Appearrance at ambient temperature: Colourless oil

Linalool is a monoterpenoid (chemically we would speak of it as an alcohol) that s found in more than 200 plant species such as citrus or labiatae - and also in cannabis - which gives them a pleasant minty and floral aroma. You will have already appreciated its smell when near thyme, lavender, laurel, cinnamon, pine, birch or mint plants. It can also be found in extracts of lemon, orange, verbena and many other essential oils. Widely used in the cosmetics industry to scent products, it is also used in detergents and soaps to give them a natural, "clean" smell.

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The maned wolf (Chrysocyon brachyurus), also known as the aguará guazú, which means 'big fox' in Guaraní, is the tallest canid in existence. Its name alludes to the long black hairs on the top of its neck, but it is also known as the 'wolf on stilts' because it has thin, endless legs (like socks and stockings) that help it to walk in pastures or flooded terrain and raise its head above the undergrowth in which it moves. Undoubtedly, the perfect result of millions of years of evolution to adapt to its environment, the extensive savannah of Brazil, although it is also found in the pampas of Peru and the scrublands of Paraguay and the northern part of Argentina.

It is a very enigmatic animal, solitary by nature (unlike other large canids, the maned wolf does not form packs) and a species rarely photographed in its environment and for which very little information exists. In fact, it is listed as endangered by the International Union for Conservation of Nature, due to intense deforestation of its habitat, a vast territory once dominated by wild grasslands that are now cultivated with eucalyptus, pine, soya bean and sunflower plantations.

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Before we start talking about the different consumption methods available, it is worth mentioning that they all have something in common: the cannabis is heated. During this process, high temperatures cause the cannabinoids to decarboxylate, turning them into pharmacologically active compounds.

Decarboxylation is a chemical reaction that removes a carboxyl group (-COOH) from a compound in the form of carbon dioxide (CO2). This process activates the plant’s cannabinoids, which are found in their acid form (like THCA and CBDA) and transforms them into the cannabinoids that we know (THC and CBD).

It is important to highlight that cannabis decarboxylation is necessary for cannabis to produce its psychoactive effects, because THC in its acid form (THCA) does not produce the psychoactivity traditionally associated with marijuana. Therefore, even when it’s being ingested, it is advisable to first heat the cannabis (cooking it in some way) to activate its components.

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From the fuel flavoured OG Kush to the citric Lemon Haze or the typically skunky Sour Diesel, there is a plethora of flavours from which marijuana lovers can choose their favourite weed.

The main components of the cannabis plant responsible for its characteristic aroma and flavour are terpenes. They are divided into monoterpenes (10 carbon atoms) and sesquiterpenes (15 carbon atoms). Depending on their proportion, variety, and combination, they can generate thousands of different organoleptic profiles. Terpenes, along with cannabinoids, develop in the plant’s resin glands (trichomes). The higher the number of trichomes, the more intense the aromatic combination.

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What is Delta-8-THC?

• Name: Delta 8 Tetrahydrocannabinol, Δ8-THC
• Formula: C21H30O2
• IUPAC name: (6aR, 10aR) -6,6,9-trimethyl-3-pentyl-6a, 7,10,10a-tetrahydrobenzo [c]chromen-1-ol
• Molecular mass: 314.5 g/mol
• Boiling point: 383.5 ± 42.0 ° C

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The cannabis that we consume today is much more potent than it was 40 years ago. If you follow the news about the industry you've most likely heard someone express some version of that sentiment. And it appears that the figures can confirm this: records show that, in the 80s, cannabis had THC levels of 2 to 5%, while today, we find many varieties that reach 20% THC on average, which backs up the claim that today's cannabis is 4-5 times more potent than it was in the 1980s.

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Many people believe we can only get CBD from cannabis, and the hemp industry has taken huge advantage of this misconception. Some consumers think they are limited to this type of CBD (cannabidiol) which can be prone to contamination, legality, and consistency issues.

Hemp-derived CBD is very cheap and useful in the right context. However, like with all things in life, it's always nice to have different options.

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What is myrcene?

• Name: Myrcene, β-myrcene
• Chemical formula: C10H16
• IUPAC name: 7-Methyl-3-methyleneocta-1,6-diene
• Density: 794kg/m3
• Molar mass: 136,23g/mol
• Boiling point: 167ºC
• Appearance: Yellowish non-water soluble oily liquid

Myrcene is one of the main terpenes found in the cannabis plant, often the most common, and certainly one of the most researched. As we already saw in our article on cannabis terpenes, these non-psychoactive organic compounds give the plants their characteristic aroma and flavour, and have different properties with a huge therapeutic potential. Terpenes - sometimes known as isoprenoids - are molecules derived from isoprene, so they are considered as hydrocarbons. They can contain 10 carbon atoms (like the compound we are discussing here - and then we’ll be talking about monoterpenes), or 15 carbon atoms, which are the so-called sesquiterpenes.

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Δ9-Tetrahydrocannabiphorol: the new holy grail of cannabis?

Towards the end of 2019, a team of Italian scientists investigating the properties of cannabis came upon something totally unexpected: two new and important cannabinoids.

These cannabinoids turned out to be very similar to regular THC (Tetrahydrocannabinol) and CBD (Cannabidiol), but with a greater number of carbon atoms in their alkyl side chain, which means their properties and even their potency are modified.

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The many different varieties of cannabis contain hundreds of compounds (the exact number is hard to calculate), each with its own characteristics and properties. You'll most likely have heard of cannabinoids, terpenes and flavonoids as components of the plant, with the first two occupying much of the general interest. However, it is estimated that flavonoids represent 10% of the total substances produced by the plant, and 2.5% of the dry weight in leaves and flowers. But what are flavonoids? What is their purpose, and how do they act? In this article we will answer these questions.

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What is CBG?

• Name: Cannabigerol
• Formula: C21H32O2
• IUPAC name: 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentylbenzene-1,3-diol
• Molecular mass: 316,48 g/mol
• Boiling point: Not available
• Apearance: White powder/crystals

Discovered by Gaoni and Mechoulam in 1964, CBG or cannabigerol is one of the cannabinoids exclusively produced by the cannabis plant, which is stored in the trichome heads with the rest of cannabinoids and terpenes. While the CBG content in most plants is often low or very low - in most cases lower than 1% - this particular compound is crucial for cannabinoid synthesis, as we have known for the past 4 decades ( (Shoyama, Yagi and Nishioka, Phytochemistry Journal, October 1975). As a general rule, hemp contains higher amounts of CBG than commercial, narcotic cannabis strains.

CBG is a non-psychoactive phytocannabinoid, which means it is produced by plants and does not "get you high". It is believed that it has multiple medicinal properties which can be used to treat different conditions, and is also precursor - its acid form, to be exact - to the main cannabinoids (THCA, CBDA, CBCA) secreted in the trichome heads, which in turn explains the low percentage of CBG found in mature plants when compared to their THC or CBD content.

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