Different Types of Cannabinoids
Delta 9 THC -Tetrahydrocannabinol (Δ9-THC)Activity: Primary psychoactive cannabinoid.Melting Point: 64 °CBoiling Point: 155 to 157 °Cor 157 to 160 °C (315 to 320 °F) at 0.05
Delta 9 Tetrahydrocannabinol, known as Δ9-THC, is a resinous, golden-brown viscous oil or fatty solid that is the principal psychoactive compound found in cannabis. Δ9-THC is usually only present at low levels in cannabis flowers because it is the product of THCA decarboxylation. The bioavailability, the proportion of a consumed compound that enters into circulation of the body, of Δ9-THC is quite variable, ranging from approximately 1 to 40 percent. The bioavailability through inhalation averages 30 percent, while the bioavailability of oral consumption is between 4 and 12 percent and much more variable. Due to its chemical properties, Δ9-THC accumulates in fatty tissue. It should also be noted that Δ9-THC has particularly poor stability, and Δ9-THC concentration in cannabis tends to decrease when frozen or exposed to light, high temperatures, or air.
Activity: Lesser psychoactive cannabinoid.
Δ8-Tetrahydrocannabinol, or simply Δ8-THC, is an isomer of Δ9-THC, having the same structural formula but a slightly different arrangement of atoms and different properties than Δ9-THC. Δ8-THC arises from the degradation of Δ9-THC, with Δ8-THC being stable in air and less psychoactive than Δ9-THC. The stability of Δ8-THC and the fact that Δ8-THC maintains the psychoactive properties Δ9-THC makes it a compound that is of interest for use in pharmaceutical products.
Tetrahydrocannabinolic acid, or THCA, is the primary cannabinoid of the Δ9-THC terpenoid group that exists in cannabis plants. THCA is known to vary in cannabis plants from approximately 0.3 to 30 percent, and concentrated cannabis products typically average between 50 and 90 percent THCA by weight. THCA is predominantly located in glandular trichomes on the surface of cannabis flowers and is synthesized from cannabigerol acid (CBGA). THCA is an aromatic, carboxylic acid that is and of itself not psychoactive, but it is the direct precursor to Δ9-THC, the primary psychoactive cannabinoid found in cannabis. THCA tends to be the most abundant cannabinoid present in cannabis products, except for concentrated products that have undergone decarboxylation. When THCA undergoes decarboxylation, from degradation during storage, vaporization, or combustion, THCA is converted into Δ9-THC. THCA is also quantitatively decarboxylized to Δ9-THC by heating a THCA-containing product to 200 to 210 °C (392 to 410 °F) for approximately 5 minutes. THCA is highly unstable and can decarboxylate to active Δ9-THC from exposure to air, light, and prolonged storage.
Tetrahydrocannabivarin, known by the acronym THCV, is an analogue of Δ9-THC and typically only occurs in cannabis plants in small amounts. THCV is given a –varin suffix because it belongs to a propyl group of compounds rather than the typical pentyl group based on its structural form. Although THCV's structural form is similar to Δ9-THC's, it has differing properties and it is unclear if THCV is psychoactive. Although it is usually only a minor cannabinoid, rare chemical profiles have been identified where THCV is the predominant compound and certain THCV-rich strains have been developed for research and development purposes.
Tetrahydrocannabivarin Carboxylic Acid, or simply THCVA, is an intermediate cannabinoid that is a precursor to tetrahydrocannabivarin (THCV). Although both THCV and tetrahydrocannabinol (THC) are both created via the THCA synthase pathway, they come from two different intermediate compounds. Unlike THC, CBD, CBG, and CBC, THCV is not synthesized from cannabigerolic acid (CBGA). Instead, THCV follows a different pathway stemming from the other intermediate cannabinoid, cannabigerovaric acid (CBGVA)—which originates from the smaller precursor divaric acid. Once the THCA-synthase enzyme creates THCVA by breaking down CBGVA, THCVA can be decarboxylated with heat or UV light to create THCV.
Cannabidiol, known by the three-letter acronym CBD, is a crystalline compound that is derived from cannabigerol acid (CBGA). CBD is the main non-psychoactive cannabinoid found in cannabis. High concentrations of CBD may lead to the production of purple-colored derivative cannabinoids that are relatively unstable. CBD itself is relatively stable when exposed to air. There is a large variance in the reported melting points of CBD, but it is suspected that CBD is not completely in a melted form until it has reached at least 80 °C. Similarly to THC, the total CBD of a cannabis product can be calculated by adding CBD with CBDA after applying the decarboxylation conversion factor;
Total CBD = CBD + (0.877 × CBDA).
In fact, CBD is actually quite structurally similar to Δ9-THC, but has a distinct biological profile. Acidic treatment can be used to convert CBD into Δ9-THC and Δ8-THC. For example, when CBD is dissolved in cyclohexane or n-hexane it is converted to THC. In general, the interesting structural features of CBD promise great potential for future research.
Cannabidiolic acid, or simply CBDA, is generated from cannabigerol acid (CBGA) and is the carboxylated precursor of cannabidiol (CBD). At its boiling point, CBDA begins to decarboxylate into CBD. CBDA synthesizes into other cannabinoids and derivative compounds as well, however, unlike CBD, CBDA cannot be converted into tetrahydrocannabinolic acid (THCA) in unprocessed cannabis.
Cannabidivarin, also known as cannabidivarol or by the acronym CBDV, is an analogue of cannabidiol (CBD) that has a unique structural form. CBDV belongs to a propyl group of compounds rather than the typical pentyl group, and is therefore given a –varin suffix. CBDV is biosynthetically produced in cannabis plants to modulate their physiological activity and is not psychoactive. Similarly to Δ9-THC and other cannabinoids, CBDV has low water solubility. Additionally, CBDV has relatively low oral bioavailability. Approximately 6 percent of CBDV is absorbed by the body when consumed orally, however, it is absorbed relatively rapidly compared to other cannabinoids.
Cannabidivarin acid, also known by the acronym CBDVA, is the acidic form of cannabidivarin (CBDV), which is in turn the propyl analogue of CBD. There is not much known about the chemical properties of CBDVA and substantial research and development is required to determine more information about the compound.
Cannabichromene, known by its three-letter acronym CBC, can be identified in certain varieties of cannabis. When present, it is suspected that CBC is a by-product from the synthesis of CBCA and Δ9-THC from CBG. CBC has been found in higher levels in vegetative cannabis plants than in mature cannabis flowers, and CBC shows as bluish-white fluorescence spots under UV light. CBC is stable, but has been demonstrated to convert into CBL. Usually, CBC is only present in small amounts. The creation of CBC in cannabis plants is determined by a recessive gene, making varieties of cannabis that are high in CBC rare.
Cannabichromenic acid, or cannabichrome carboxylic acid (CBCA), is the predominant form of cannabichromene (CBC) found in cannabis plants. CBCA has been identified in the leaves of both immature and mature cannabis plants. The CBCA Synthase enzyme converts CBGA present in a cannabis plant to CBCA in a similar manner as the THCA synthase enzyme converts CBGA to THCA, CBDA, and other intermediate cannabinoids. Decarboxylation of CBCA, which occurs rapidly above 105° C, generates CBC. CBCA can be synthesized from cannabidiol (CBD) and tetrahydrocannabinol (THC) through the use of nonenzymatic decarboxylation.
Cannabigerol, known by its three-letter acronym CBG, is typically only present in minute amounts. High concentrations of CBG may lead to the production of certain derivative cannabinoids that are purple-colored and highly unstable. Most of CBG's derivatives are minor or trace constituents of cannabis that are difficult to detect. CBG has the lowest oxidation level of all cannabinoids CBG can be converted to CBD, THC, and CBN. CBG is non-psychoactive. The molecular structures of cannabinoids that are derivatives of CBG inherit CBG's characteristic aromatic ring. CBG has been identified as the predominant compound in certain rare chemical profiles.
Cannabigerol acid, or simply CBGA, is the precursor of all other types of cannabinoids, and the direct precursor of tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA), and cannabichromenic acid (CBCA). CBGA is derived from olivetolic acid and geranyl pyrophosphate and is also relatively easy to synthesize.
Cannabicyclol, known by its three-letter acronym CBL, is not thought to be psychotropic and is not scheduled by the Convention on Psychotropic Substances, the United Nations treaty designed to control psychoactive drugs. CBL belongs to a group of compounds that also includes cannabicyclolic acid A (CBLA) and cannabicyclovarin (CBLV). It is suspected that CBL may not be a genuine cannabinoid, but instead an artifact that is produced by natural irradiation of cannabichromene (CBC) and cannabichromenic acid (CBCA) from light exposure and during storage. The evidence for this is that CBL and its acidic form, CBLA, are found in higher levels when cannabis plants are harvested earlier rather than later.
Cannabinol, known by its three-letter acronym CBN, is a crystalline alcohol that is a minor by-product of Δ9-THC oxidation and not biosynthetically produced by the cannabis plant itself. CBN is a fully aromatized derivative of THC. As cannabis plants become ready to harvest, their glandular trichomes will transition from a clear or milky-white color to brown as Δ9-THC is converted into CBN. After harvest and over time, the concentration of CBN found in cannabis increases as Δ9-THC slowly degrades, however, at a different rate than Δ9-THC decreases. CBN is slightly psychoactive, but much less so than Δ9-THC. CBN is also combustible, will burn easily, and is one of the major metabolites of cannabis consumption. There are a variety of CBN-type cananbinoids, with 10 currently identified. It has been determined that CBN primarily degrades into cannabinodiol (CBND), a weakly psychoactive cannabinoid that is usually only present at very low levels.
Cannabinolic Acid (CBNA) is the acidic precursor to CBN. Unlike other commonly known cannabinoids, CBNA is not derived directly from CBGA or CBGVA, rather it is a metabolite of THCA oxidation. If cannabis products are exposed to heat, air, or UV light for prolonged periods of time, then any THCA that is present can degrade to CBNA, which, when decarboxylated, forms CBN. CBNA can also be synthesized from tetrahydrocannabinolic acid (THCA) by aromatization using selenium dioxide mixed with trimethylsilyl polyphosphate as catalyst in chloroform.