Throughout the entire cannabis species, you will find a host of therapeutic molecules – Such as cannabinoids, terpenes, and flavonoids; collectively offering over a thousand varieties, with the most abundant being the cannabinoids THC (tetrahydrocannabinol), and CBD (cannabidiol). In this article, I will guide you through the cannabinoid, CBD and its molecular analogues.
To fully understand the different analogues of CBD, I recommend that you learn a little about the lifecycle of cannabinoids and their avenues of mutation.
The Transformation Of Cannabinoids
Among wildlife and specifically modified growing facilities, there are over 40 thousand unique cannabis cultivars. Combined, this vast range plays host to in excess of one hundred unique cannabinoids. Regardless of the species, only a few cannabinoids are present at the beginning of their lifecycle.
Before we get to the dominant cannabinoids such as THC, and CBD, the plant’s journey begins with either of the analogues to “the mother of all cannabinoid” CBG (cannabigerol): CBGA (cannabigerolic acid) and CBGVA (cannabigerovarinic acid). These cannabinoid precursors are prevalent in almost every cannabis seed.
During the crop period, the cannabinoid precursors create a whole catalogue of acidic cannabinoids. The resulting acidic cannabinoids are determined by the breed of seed. Amidst a collection of newly spawned cannabinoids, you’ll find the first two analogues of CBD: CBDVA (cannabidivarinic acid) and CBDA (cannabidiolic acid).
The metamorphosis of cannabinoids continues after processes known as decarboxylation and oxidation, thus mutating the cannabinoids into either a neutral or oxidative state. Whether induced manually or by mother nature, the results are the same: Additional cannabinoids, and plenty of them!
The Cannabinoid Molecular Analogues
After the primary cannabinoids THC and CBD, there’s CBG (cannabigerol), which is steadily joining the duo as a dominant cannabinoid. Next on the list, you’ll find “lesser” cannabinoids, such as CBC (cannabichromene) and CBL (cannabicyclol). All of which feature in the three primary families of researched cannabinoid analogues: Acidic, neutral, and varinoid. But… there are more!
The cannabinoids CBD and CBDA are analogues of one another, and likewise with THC and THCA, or CBG and CBGA.
Analogues vary largely because of the length of their molecular alkyl side chain and the number of carbon atoms present.
Currently, eight-core analogues have been identified:
- CBD (cannabidiol)
- THC (tetrahydrocannabinoil)
- CBG (cannabigerol)
- CBC (cannabichromene)
- CBN (cannabinol)
- CBT (cannabitriol)
- CBL (cannabicyclol)
- CBE (cannabielsoin)
As a result of the “Marijuana Tax Act”, cannabis scientific research was restricted and had barely scratched the surface, however, with recent legislation changes, the brakes have been lifted.
We most likely still haven’t yet discovered every molecular analogue, and consequently, every cannabinoid. For instance, in the twilight hour of 2019, Italian researchers discovered two additional cannabinoids, THCP (tetrahydrocannabiphorol) and CBDP (cannabidiphorol).
Not only did this discovery add two further cannabinoids to the inventory, but also a whole new analogue!
The researchers acclaimed for the discovery have dubbed the new cannabinoid analogue as “phoral”.
What Are CBD’s Molecular Analogues
The discovery of THCP and CBDP welcomed a new cannabinoid analogue to the family, but to date, whether minor cannabinoids such as CBG, CBC, and CBL, have a “phoral” equivalent remains a mystery.
In recent years, CBD is possibly the most researched cannabinoid. Let’s take a look at its analogues:
CBDA – Cannabidiolic acid
In CBD dominant cannabis strains, CBDA is the most commanding cannabinoid, pre-decarboxylation. Every neutral cannabinoid has its acidic precursor – In this instance, cannabidiolic acid is the direct predecessor of cannabidiol.
Additionally, CBDA can convert into a whole new core analogue. If a process known as photo-oxidation occurs, CBDA will transform into CBEA (cannabielsoic acid) – which is the acidic analogue of CBE.
In hemp, CBDA is one of the first cannabinoids to materialise during the crop period, the cannabinoid naturally mutates and descends directly from CBGA.
CBDVA – Cannabidivarinic acid
In a similar fashion to CBDA – CBDVA evolves from its precursor during the crop period. Only this time, its mother cannabinoid is CBGVA.
Once again, the complex science continues to impress as CBDVA is another cannabinoid that can remodel itself and generate a second ancestor of CBE, by transforming into CBEVA-B (cannabielsovarinic acid B).
CBDVA is both acidic and a varinoid and is the cannabinoid precursor of CBDV.
CBD – Cannabidiol
The cannabinoid that everyone is talking about – CBD is the second most abundant cannabinoid within the cannabis family after decarboxylation.
Although powerful in presence, CBD plays a small role in the lifecycle of cannabinoids. Its only ancestor is its acidic equivalent, CBDA, and its only offspring is CBE – which again, occurs after the process known as photo-oxidation.
CBD will also go down in history as the first cannabinoid to be approved as a pharmaceutical ingredient in GW Pharmaceuticals, Epidiolex. The drug has been manufactured for the treatment of seizures associated with two rare and severe forms of epilepsy, Lennox-Gastaut syndrome, and Dravet syndrome, in patients two years of age and older.
CBDV – Cannabidivarin
CBDV is the neutral-varin offspring of CBDVA. Given time and oxygen, CBDV can go on creating two additional cannabinoids, as oxidation will alter CBDV’s molecular structure and create CBEV (cannabielsovarin) or CBNDV.
As CBDV offers additional attributes of CBD, regarding its potential to aid with the treatment of epilepsy, it too is under the radar of GW Pharmaceutical and could well be the second cannabinoid to be an FDA approved cannabinoid as an ingredient to a pharmaceutical product.
CBDB – Cannabidibutol
A new arrival to the world of cannabinoids is CBDB. The cannabinoid was discovered last year by a group of Italian researchers, CBDB was discovered along with THCB (tetrahydrocannabutol).
Not much is known about CBDB as it is in low quantities and as far as we know, indigenous to one cannabis strain: FM2, a Cannabis Sativa variety produced by the Military Pharmaceutical Plant in Florence.
All that research has told us thus far is that the new cannabinoids exist from an entirely new analogue, dubbed as “butol”.
CBDP – Cannabidiphorol
The latest revelation from the cannabis species is the entirely new analogue “phoral”. The same group of Italian scientists behind the “butol” discovery struck again when they discovered THCP (tetrahydrocannabiphorol) and CBDP.
THCP is a mouthwatering prospect for cannabis researchers as it showcases a potent affinity with the CB1 receptor. Whereas CBDP shows little affection to bond with the receptor, so don’t expect any groundbreaking research with cannabidiols “phoral” equivalent.
Are There Any Other CBD Analogues?
Although the cannabis plant consists of over 100 cannabinoids, the reality is that we don’t know much about the majority of them.
More CBD derivatives have been explored, such as CBDM (cannabidiol monomethyl ether), which also has an acidic equivalent: CBDAM (cannabidiolic acid monomethyl ether). The rare cannabinoid has been successfully isolated from a Japanese hemp strain – Minamioshihara No. 1.
My research has also brought CBDD (cannabidiol dimethyl ether), CBD-C1 (Cannabidiorcol), and CBD-C4 (cannabidiol-C4) to my attention, but the information is currently scarce.
This further reinforces the cannabis plants’ marvel, as studying the plant only opens up further questions. To quote Einstein – “The more I learn, the more I realise how much I don’t know”.
The entire life-cycle of cannabinoids is fascinating. With well over 100 cannabinoids confirmed to date, the fact that the journey begins with only the acidic analogues of “the mother of all cannabinoids” CBG is incredible.
Dependant on the cannabis seed and processes such as decarboxylation, oxidation, and photo-oxidation – the molecular structure of cannabinoids can alter into a collection of acidic, acidic-varins, neutral, or oxidative cannabinoids.
And let’s not forget that cannabis-based research is accelerating at a staggering pace. With eight core analogues, CBD and its molecular analogues are just the tip of the iceberg.
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