Propyl Cannabinoids

It is especially interesting that the duration of action of the propyl cannabinoids is significantly shorter than that of the pentyl compounds. Smoking marijuana with large amounts of THCV should produce a shorter high than usual, but human ex- 

Cannabinoids and Propyl Cannabinoids of High Potency Strains 

AH values are % of total cannabinoids rounded off to nearest % THCV Tetrahydrocannabivarin CBDV = Cannabidivarin T 1% 

SEED ORIGIN GROWN IN CONDITION THC THCV CBD CBDV 

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Shoyama Y, Hirano H, Makino (nee Tomita) H, Umekita N, Nishioka I, Cannabis. 10. Isolation and strucmres of 4 new propyl cannabinoid acids, tetrahydrocannabivarinic acid, cannabidivarinic acid, cannabichromevarinic acid and cannabigerovarinic acid, from thai cannabis, Meao variant, Chem Pharm... 

Shoyama Y, Hirano H, Nishioka I, Cannabis. Part 16. Biosynthesis of propyl cannabinoid acid and its biosynthetic relationship with pentyl and methyl cannabinoid acids, Phytochemistry 25 1909—1912, 1984. 

The propyl cannabinoids corresponding to A -tetrahydrocannabinol [(424) = A -THC], cannabichromene (425), cannabidiol (426), and cannabivarin (427 R = Pr) have been found, particularly in Asian Cannabis, and methods for their detection, identification, and evaluation have been discussed. 

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. 

In their next study, Shoyama and Nishioka isolated new spirocom-pounds cannabispirol and acetyl cannabispirol. This is in addition to the already known cannabispirone and cannabispirenone from a Japanese hemp variety. The two scientists included them in their biogenetic schema alongside the cannabinoid acids. In a further study, Shoyama et al. dealt with the biosynthesis of propylcannabinoid acids by in vitro incubation with raw enzyme solution from three species of Cannabis sativa KL. A biogenetic schema is presented illustrating the relationship between methyl, propyl and pentyl cannabinoid acids. 

Breimer. Cannabivarichromene, a new cannabinoid with a propyl side chain in Cannabis. Experientia 1973 29 260. 

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... 

Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, Fan P, Makriyannis A, Tius MA (1998) Classical/nonclassical hybrid cannabinoids southern aliphatic chain-functionalized C-6/ methyl, ethyl and propyl analogues. J Med Chem 41 3596-3608... 

Tetrahydrocannabivarinic acid, cannabidivarinic acid, cannabichromevarinic acid, and cannabigerovarinic acid are the C-3" carboxylic acid derivatives of known propyl side-chain cannabinoids, ° and others are propyl homologues of cannabichromanone, cannabielsoin, and cannabielsoic acid Turner et al. have reported an additional triol (240) from Cannabis sativa ... 

Fig. 1. Some naturally occurring cannabinoids. The top three compounds are by far the most important, with the set of three compounds below being identical except that the side chain is shortened by 2 carbon atoms in the cannabidivarol series. Later in the text look for a discussion of the series with the propyl side chain, and see the Appendix for the numbering system used. (Reprinted, by permission, from R. Mechoulam, Mar/yt/ana, 1973.)...

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