Cannabinoid Discoveries: Cannabicitran and Cannabitriol

In classifying the kinds of cannabinoids there are, three main categories are recognized: the phytocannabinoids, which occur naturally in the cannabis plant, the endocannabinoids, found in the human body, and the chemically-synthesized cannabinoids. Many phytocannabinoids have been identified, and research continues to discover others.

Let’s take a look at one of the most recent discoveries in phytocannabinoid science.

PHYTOCANNABINOIDS

The cannabis plant embodies a cornucopia of chemical compounds, of which their combined effect confers specific traits on the plant via the entourage effect. The percentage content of each of these constituents further divides the plant into three primary types: the type I; characterizing cannabis plants with high-level tetrahydrocannabinol (THC) (>0.3%) and low-level cannabidiol (CBD) (<0.5%), making it psychotropic, the type II kind, with a mixed ratio of CBD and THC, often with the former been predominantly present; thus, subduing the intoxicating effect of the constituent THC, and the type III with a high CBD percentage composition with trace levels of THC. Other types include the type IV and type V; ‘CBG dominant’ and the ‘no cannabinoids’ variants.

There are over 100 cannabinoids and 400 compounds in the cannabis plant, and several of these constituents remain unexplored; however, with favorable modifications to laws regarding the plant, more of these hidden compounds are now being explored – two of which are the cannabicitran and cannabitriol.

CANNABICITRAN AND CANNABITRIOL

In early times, CBG was believed to be the sole precursor molecule in the cannabis’ tree,’ producing several cannabinoids including CBD and THC; but this has been rendered invalid with studies showing Cannabichromene (CBC) (also a phytochemical) further branches into the CBTs – Cannabitriol. Since its discovery in 1966, scientists have analyzed and confirmed the presence of at least nine different types of CBT, each with a slight difference in their molecular structure and base compound.

CANNABICITRAN

Cannabicitran, otherwise known as CBT-C, is one of the many subsets of this compound biosynthesized in cannabis amongst the olivetol series. The compound, found at peak concentrations in distillates (1 – 5%) from the Cannabis sativa (type III), is believed to be synthesized from the precursor molecule CBDA; hence its low psychotropicity.

Before its identification in the Lebanese Hashish, a similar compound, the “cytrilidene cannabis,” had been earlier synthesized by chemist Leslie Crombie in 1971. This compound was called so due to its bearing similarity to a natural product from the cannabis plant – discovered in subsequent years. Since this phytocannabinoid’s isolation, many theories as to what it functions as and its benefits have arisen and been disputed. Nevertheless, a study conducted by Mahmoud Elsohly discovered CBT to reduce eye pressure in rabbits; thus, making it a potential treatment for glaucoma and other related conditions.

As one of many phytocannabinoids, Cannabicitran, classified as a di-ether compound, has an analogous chemical relationship to CBD, as CBD is to THC, and can be said to contribute to the entourage effect of the plant. Thanks to this relationship, it is garnering popularity as a therapeutic element in the hemp industry and is now being formulated into tinctures, oils, extracts, and concentrate forms.

Due to the restrictions on cannabis legislation, there have been limited studies regarding the benefits and adverse effects of cannabicitran. However, in 2007, research to identify THC’s addictive effects – seeking mitigators to the psychoactive components of THC- showed that CBT-C served as an antibody to the chemical transformation caused by THC and will thus serve as an effective dampener to the psychoactive effects of the THC.

The cannabinoid, CBT-C, can also serve as a marker during chromatographic testing of cannabinoids since it is retained the longest on the column during analysis; hence, it is indicative of the completion of sample analysis. The first online reference to CBT-C goes as far back as 1970 when a chemist using the normal-phase flash chromatography, isolated CBG from a CBD-rich hemp distillate. Seeing this technique’s effect, he thought of reversing the process using the reversed-phase flash chromatography, which enabled him to collect other compounds, including Cannabicitran.

In 2011, CBT-C was finally confirmed as a cannabinoid in a journal publication on examining the male Cannabis sativa L. using a modern chromatographic method – the gas chromatography with flame ionization detector and the gas chromatography-mass spectrometry. Contrary to the class affiliated to the compound, it has also been isolated from the Chinese medicinal plant Rhododendron Anthopogonoides, used extensively in treating bronchitis and other respiratory ailments.

More data on the features and benefits of this compound remain quite inadequate, but with the expansion of knowledge and more openness to discovering the hidden treasures, the focus can now turn towards understanding the other minor cannabinoids.

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