CANNABICYCLOVARIN (CBLV)

What is Cannabicyclovarin (CBLV)?

Cannabicyclovarin (CBLV) is a type of Cannabinoid compound that has its boiling Point (F) as 666 ± 88 and boiling Point (C) as 352 ± 31. It belongs to the class of the cannabicyclols in the Cannabinoids locator.

Cannabinoids are one of the many compounds produced by Cannabis and there is over a hundred of it with CBD, THC and CBN being the most common. Most Cannabinoids are not directly produced by the Cannabis plant as there is a biosynthetic pathway that results in the production of these cannabinoid acids.

This pathway synthesizes the cannabinoid acids through the process of decarboxylation because there is a need for the cannabinoid acids to be activated by heat to yield the desired compound which can then subsequently be decarboxylase into the corresponding cannabinoids in which Cannabicyclols (CBL) falls.

Cannabicyclol is a phytocannabinoid which came to be as a result of the myriad compounds synthesized in the resinous trichomes of Cannabis sativa plants.

This class of cannabinoid forms from the breakdown of CBC using the presence of heat and light. This explains why older cannabis has higher levels of CBL than the fresh ones. Even at that, the amount always present is low.

Cannabicyclovarin (CBLV-C3) was first detected by GC-MS and later isolated as optically inactive colorless needles.

Its structure was confirmed by comparison with synthetic CBLV-C3 obtained by irradiation of CBCV-C3. However, before arriving at Cannabicyclovarin acid (CBLV), the compound being in the class of cannabicyclols had undergone many processes just as it was noted by a group of researchers.

Related: What is CBN?

Cannabicyclol (CBL-C5) was first considered to have a THC-type structure , and was therefore named THC III. It was isolated in 1967, renamed to cannabicyclol/cannabipinol and the structure revised.

The photochemical conversion of cannabichromene into cannabicyclol prompted another revision of the structure and speculation about the origin of the compound, i.e., if it is a naturally occurring compound or an artefact Cannabicyclol from the crude plant material shows no apparent optical rotation, although an [a]D 3-was reported , and it could form as a result of natural irradiation in the plant or it could be an artifact formed in the crude extract.

This structure was finally confirmed as the correct structure by NMR and X-ray analysis, although the absolute configuration is not yet known.

HOW IT WORKS

Cannabicyclovarin occurs as a natural cannabinoid in Cannabis sativa. Cannabis sativa is a medicinal plant having a very complex matrix composed of mainly cannabinoids and terpenoids.

Related: CBD vs CBN

THERAPEUTIC BENEFITS

Because very little is known of the CBL due to its low concentration, little can be said of its therapeutic benefits. However, as a family of cannabicyclols (CBL) having CBC as its precursor, Cannabicyclovarin has many essential functions within the body such as increasing the levels of certain helpful chemicals in the body like the endocannabinoids. 

As a phytocannabinoid, it has potential benefits such as the stimulation of appetite, relieving pain and inflammation, reduction of nausea, and a range of other benefits.

INTERESTING FACTS

It helps to maintain a state of balance (homeostasis) in the body.

References

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Crombie, L., Ponsford, R., 1968. Synthesis of hashish cannabinoids by terpenic cyclization. Chemical Communications 15, 894–895.

Kane, V.V., 1971. Structure of cannabicyclol. Detailed NMR study of a synthetic analog. Tetrahedron Letters 44, 4101–4104.

Korte, F., Sieper, H., 1964. Chemical classification of plants. XXIV. Hashish constituents by thin-layer chromatography. Journal of Chromatography 13 (1), 90–98.

Mechoulam, R., Gaoni, Y., 1967. Recent advances in the chemistry of hashish. Fortschritte der Chemie Organischer Naturstoffe 25, 175–213.

Ramesh Jagannathan, “Identification of Psychoactive Metabolites from Cannabis sativa , Its Smoke, and Other Phytocannabinoids Using Machine Learning and Multivariate Methods” AMC Omega, 2020 Jan 3; 5(1): 281–295.

Shoyama, Y., Morimoto, S., Nishioka, I., 1981. Cannabis. XIV. Two new propyl cannabinoids, cannabicyclovarin and D7-cis-iso-tetrahydrocannabivarin, from Thai cannabis. Chemical and Pharmaceutical Bulletin 29 (12), 3720–3723.

Vree, T.B., Breimer, D.D., Van Ginneken, C.A.M., Van Rossum, J.M., 1972. Gas chromatography of cannabis constituents and their synthetic derivatives. Journal of Chromatography 74 (2), 209–224. Whiting, D.A., Begley, M.J., Clarke, D.G., Crombie, L., 1970. X-ray structure of dibromocannabicyclol: structure of bicyclomahanimbine. Journal of the Chemical Society, Chemical Communications 22, 1547–1548.