Comparison Of Phytocannabinoids
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Cannabinoids () are compounds found in the cannabis plant or synthetic compounds that can interact with the
endocannabinoid system The endocannabinoid system (ECS) is a biological system composed of endocannabinoids, which are neurotransmitters that bind to cannabinoid receptors, and cannabinoid receptor proteins that are expressed throughout the central nervous system ( ...
. The most notable cannabinoid is the phytocannabinoid
tetrahydrocannabinol Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of ''Cannabis'' and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) de ...
(THC) (Delta-9-THC), the primary intoxicating(at too much dose) compound in
cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species be ...
.
Cannabidiol Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in ''Cannabis'', along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat multiple f ...
(CBD) is another major constituent of some cannabis plants.
Conversion of CBD to THC Conversion (chemistry), Conversion of cannabidiol (CBD) to tetrahydrocannabinol (THC) can occur through a ring-closing reaction. This cyclization can be acid-catalyzed or brought about by pyrolysis, heating. Known methods Comparison of phytocanna ...
can occur when CBD is heated to temperatures between 250–300 °C (480 to 570°F), potentially leading to its partial transformation into THC. At least 113 distinct cannabinoids have been isolated from cannabis. This article gives comparative structures of some of the more common natural and synthetic cannabinoids, as well as showing structures of legally banned and sanctioned cannabinoids.


Structures


Legality


Thermal properties


Conversion temperatures


Decarboxylation temperatures

All cannabinoids listed here and their acids are found naturally in the plant to varying degrees. Upon heating, cannabinoid acids
decarboxylate Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...
to give their psychoactive cannabinoid. For example,
Delta-9-tetrahydrocannabinol Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of ''Cannabis'' and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) de ...
(THC) is the main psychoactive compound found in cannabis and is responsible for the "high" feeling when consumed. However, cannabis does not naturally contain significant amounts of THC. Instead,
tetrahydrocannabinolic acid Tetrahydrocannabinolic acid (THCA, 2-COOH-THC; conjugate base tetrahydrocannabinolate) is a precursor of tetrahydrocannabinol (THC), an active component of cannabis. THCA is found in variable quantities in fresh, undried cannabis, but is prog ...
(THCA) is found naturally in raw and live cannabis and is non-intoxicating. Over time, THCA slowly converts to THC through a process of
decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...
over the course of roughly a year, but can be sped up with exposure to high temperatures. When heated under conditions of 110 °C, decarboxylation generally occurs in 30–45 minutes. The decarboxylated THCA (THC) is added to
cannabis edible A cannabis edible, also known as a cannabis-infused food or simply an edible, is a food item (either homemade or produced commercially) that contains decarboxylated cannabinoids (cannabinoid acids converted to their orally bioactive form) fro ...
s, as THCA is not orally active. When consumed orally, the
liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...
breaks down and
metabolizes Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
THC into the more potent 11-hydroxy-THC.


Vaporization temperatures

Dry-herb vaporizers can be used to inhale
cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species be ...
in its flower form. There are 483 identifiable chemical constituents known to exist in the
cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species be ...
plant, and at least 85 different cannabinoids have been isolated from the plant. The aromatic terpenoids begin to vaporize at , but the more bioactive tetrahydrocannabinol (THC), and other cannabinoids also found in cannabis (often legally sold as cannabinoid isolates) like cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN), do not vaporize until near their respective
boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envi ...
s. The cannabinoids listed here are found in the plant but only in trace amounts. However, they have also been extracted and sold as isolates online. Third party certification may help ensure buyers to avoid
synthetic cannabinoid Synthetic cannabinoids, or neocannabinoids, are a class of designer drug molecules that Binding affinity, bind to the same receptors to which cannabinoids (Tetrahydrocannabinol, THC, Cannabidiol, CBD and many others) in cannabis plants attach. Th ...
s.


Structural scheduling


References

{{Cannabinoids Drug-related lists Comparison of psychoactive substances