Cannabidiol CBD

The lUPAC name of cannabidiol is 2-[(lS, 6iI)-3-methyl-6-prop-l-en-2-yl-l-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol. Cannabidiol (CBD, 2.9) in its acidic form cannabidiolic acid (CBDA, 2.10) is the second major cannabinoid in C. sativa besides A9-THC. As already mentioned for A9-THC, variations in the length of the side chain are also possible for CBD. Important in this context are the propyl side chain-substituted CBD, named cannabidivarin (CBDV, 2.11), and CBD-C4 (2.12), the homologous compound with a butyl side chain. Related to the synthesis starting from CBD to A9-THC as described in Sect. 3.1, it was accepted that CBDA serves as a precursor for THCA in the biosynthesis. Recent publications indicate that CBDA and THCA are formed from the same precursor, cannabigerolic acid (CBGA), and that it is unlikely that the biosynthesis of THCA from CBDA takes place in C. sativa. 

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There is much interest in the medical applications of Cannabis sativa L. (marijuana). An oral spray consisting of the marijuana constituents, cannabidiol (CBD,19) and A -mzw-tetrahydrocannabinol (THC, 20), has been approved recendy in Canada for the treatment of neuropathic pain associated with multiple sclerosis (MS), and it is possible that this drug will be approved elsewhere in the near future. ... 

Until the mid 1960 s the only plant cannabinoid whose structure was fully elucidated was cannabinol (CBN) — a constituent which actually may represent an oxidation artifact. However, on the basis of CBN, the main cannabinoid structure skeleton became known. Thus, cannabidiol (CBD), which had been independently isolated in pure form by Adams and by Todd, was correctly assumed to be, like CBN, a terpenoid derivative attached to olivetol. But its exact structure was not elucidated. The psychoactive components of cannabis were assumed to be related tricyclic derivatives. On the basis of the tentatively elucidated constituents, Todd suggested that the cannabinoids may be formed initially in the plant by condensation of a menthatriene with olivetol. 

A second cannabis constituent, cannabidiol (CBD) was also isolated, but its structure was only partially clarified. Synthetic tetrahydro-cannabinols, which showed cannabis-like activity in animal tests, were prepared, but they obviously differed from the active natural product, on the basis of their UV spectrum. 

More than 400 chemical compounds have been identified in marijuana. Approximately 60 of these are unique to the cannabis plant, substances called cannabinoids. Of the cannabinoids, a group of isomers (chemically similar substances) called tetrahydro-cannabinols (THC) are thought to be the most psychoactive. These are Ai-THC (also called A9-THC) and A6-THC (also called A8-THC). Other cannabinoids include cannabidiolic acid (CBDA), cannabidiol (CBD), and cannabinol (CBN). Their role in marijuana intoxication is less well understood. The amount of THC produced depends on the strain of cannabis and on environmental factors such as growth, harvest, and storage conditions. 

Phytocannabinoids are natural compounds present in Cannabis sativa, responsible for the pharmacological and toxicological properties of this plant. About 70 compounds belong to this class, the most important are A9-tetrahydrocannabinol (THC), cannabinol (CBN), and cannabidiol (CBD). 

The methods used to identify cannabis products depend upon the nature of the products themselves. Herbal material can be identified on the basis of its morphological characteristics alone, provided that certain of these are present. Where they are not, and in the case of resin and hash oil, the identification is made on the basis of phytochemical identification and the proof of the presence of A -THC (1), its precursor, cannabidiol (CBD) (3) and its breakdown product, cannabinol (CBN) (4). However, it should be remembered that the presence of the breakdown product, CBN, precludes the use of the sample for comparative purposes. 

Cannabidiol (CBD) is a non-psychotropic component of cannabis with possible therapeutic use as an anti-inflammatory drug. Recent studies on both enantiomers of CBD showed enantioselectivity in their interaction with cannabinoid and vanniloid (VRl) receptors as well as on the cellular uptake and enzymatic hydrolysis of anandamide (Bisogno et al. 2001). 

Marijuana, or Cannabis sativa, has been valued for its medicinal as well as its psychotropic properties dating back to ancient times. However, reports from as early as the 1960s have indicated that marijuana and select components also could compromise human health, including the ability to resist infections. Included among these components is a class of compounds collectively known as cannabinoids. At least 60 have been identified. These include cannabidiol (CBD), cannabinol (CBN), cannabigerol (CBG), and A -tetrahydrocannabinol (THC), the major psychoactive ingredient in marijuana that has been implicated as the major immunomodulatory substance. 

Cannabis samples Cannabinol (CBN), Cannabidiol (CBD), A8-and A9-tetra-hydrocannabinol (A8-and A9-THC) in a Cannabis extract Partition ODS-bonded silica Methanol/0.02N sulphuric acid (80 20)... 

Treatment with FBS-NaOFI reagent shows intense red-violet to red-orange zones (vis.). Hashish samples 1 and 3 show two prominent red zones in the R, range 0.45-0,55 due to cannabinol (CBN) and cannabidiol (CBD),... 

Figure 7.10. Phencyclidine is oxidized to an iminium species whose role as an intermediate in the inactivation of P450 enzymes is unclear. The structure of cannabidiol (CBD), which also inactivates P450 enzymes by an undefined mechanism, is also shown.

Modification of the P450 protein is also observed with cannabidiol (CBD) (Figure 7.10), a... 

Classification Marijuana ( grass ) is a collective term for the psychoactive constituents present in crude extracts of the plant Cannabis sativa (hemp), the active principles of which include the compounds tetrahydrocannabinol (THC), cannabidiol (CBD), and cannabinol (CBN). Hashish is a partially purified material that is more potent. 

The proposition that cannabidiol (CBD), a nonpsychoactive component of the cannabis plant, possesses considerable antipsychotic activity (Znardi and Gmmaraes, 1997) is supportive of the self-medication role of cannabis in the disorder, but this action is not via the cannabinoid CBj receptor. 

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