Cannabigerol

Cannabigerol (CBG, 2.6) was historically the first identified cannabinoid [9]. It can be comprehended as a molecule of olivetol that is enhanced with... 

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. 

Several additional, non-psychotropic cannabinoids were also identified at that time. The best known are cannabigerol (CBG), cannabichromene (CBC) and cannabicyclol. Cannabinolic acid (CBNA) and cannabigerolic acid (CBGA) were also identified,followed by two... 

Gaoni Y, Mechoulam R, The structure and synthesis of cannabigerol, a new hashish constituent, Proc Chem Soc 82, 1964. 

Mechoulam R, Gaoni Y, The isolation and structure of cannabinolic, cannabid-iolic and cannabigerolic acids. Tetrahedron 21 1223-1229, 1965. 

Shoyama Y, Yamauchi T, Nishioka I, Cannabis. 5. Cannabigerolic acid monomethyl ether and cannabinoHc acid, Chem Pharm Bull 18 1327—1332, 1970. 

Taura F, Morimoto S, Shoyama Y, Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic 2lcsA, J Biol Chem 271 17411—17416, 1996. 

Cannabielsoin, C-3 Resin Cannabielsoin P1CS172 Cannabifuran, dehydro Resin , Pl snz Cannabifuran Pl snz Resin Cannabigerol monomethyl ether Pl siZZ Cannabigerol Resin ° , Pl s i i Cannabigerolic acid monoethyl ether ... 

The oxidocyclization of cannabigerolic acid to tetrahydrocannabinolic acid is catalyzed by tetrahydrocannabinolic... 

Cannabinoids (cannabigerol, cannabidiol, cannabinol, A-9-tetrahydrocannabinol, A-8-tetrahydrocannabinol, cannabichromene, A-9-tetra-hydrocannabinolic acid)... 

Cannabis constituents Cannabicyclol Cannabidiol Cannabigerol Cannabinol... 

Fellermeier, M. and Zenk, M.H. (1998) Prenylation of olivetolateby a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEES Lett., 427, 283-85. 

Two new propyl-side-chain cannabinoids are propyl homologues of cannabi-chromene and cannabigerol. Butyl homologues of A -THC, cannabinol, can-nabidiol, and A -tetrahydrocannabinolic acid have been detected. The structure of cannabispiran (257) has been determined by X-ray analysis. By observing the... 

C]MVA, [l- H]geraniol, and [l- H]nerol were all incorporated into can-nabichromenic acid (120) and tetrahydrocannabinolic acid (121) by Cannabis sativa, and [car oxy- CJcannabigerolic acid (122) labelled these two compounds and also cannabidiolic acid (123). The results probably show that cannabigerolic... 

The major psychoactive substance in marihuana was finally isolated and identified in 1964 by two Israeli chemists, Y. Gaoni and R. Mechoulam, as l-delta-9-trans-tetrahydrocannabinol (delta-9 -THC). Subsequently, a number of other cannabinoids have been identified which either exert some biological effects of their own or else modify the effects of delta-9-THC, among which are delta-8-THC, cannabicyclol, cannabichromene, cannabigerol, cannabivarol, cannabidivarol, and a long list of similar compounds. 

The two major tests up until very recently have been the Beam and Duquenois tests. In the Beam test, cannabis is mixed with alcohol and potassium hydroxide. If a purple color develops, cannabis is presumed present. The Beam test, however, is more sensitive to some cannabinoids (e.g., cannabidiol and cannabigerol) than others, and the mixture will not turn purple if these cannabinoids are missing. The Duquenois test involves mixing the unknown substance with vanillin, acetaldehyde, alcohol, and hydrochloric acid. If a violet color develops, the test substance is presumed to be cannabis. Although the Duquenois test is more sensitive than the Beam test, it is not as specific - a violet color will also develop in the presence of other substances, e.g., coffee. 

Cascio MG, Gauson LA, Stevenson LA et al (2010) Evidence that the plant cannabinoid cannabigerol is a highly potent a2-adrenoceptor agonist and moderately potent 5HTiA receptor antagonist. Br J Pharmacol 159 129-141... 

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. 

On topical application in mineral oil, a somewhat different order of activity was recorded A6-THC > A -THC 3 6a-OH-A -THC > CBD > 7-OH-A -THC > 6,7-dihydroxy-A -THC > 7-OH-A6-THC > 60-OH-A -THC [214], These results do not follow the well-established cannabimimetic SAR. This conclusion is strengthened by the recent observation that the naturally occurring cannabigerol (48), which is not cannabimimetic, reduces IOP in the cat and moreover showed reverse tolerance (in being more effective after chronic administration than in acute one) [215]. 

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