Don’t worry, Naturally Occurring Molecules can be Chiral but such Phytocannabinoids are Not Making a Political Statement.

Let’s use Cannabichromene (CBC) as an example. First the Facts:

1. CBC is a naturally-occurring so-called “minor” cannabinoid and is increasingly in demand by formulators to make more effective remedies and medicines and may be an important contributor to the entourage effect.

2. CBC has its own properties as well as some overlapping qualities with both CBD and CBG. CBC has and is being studied for potential anti-microbial, anti-fungal and anti-inflammatory effects.

3. CBC is not scheduled as a controlled substance.

4. CBC does not crystallize at high purity levels but remains as an oil.

5. Chemical Description:

Formula: C21H30O2

Molar mass: 314.46 g/mol

ChemSpider ID: 28064

6. PPM produces and purifies CBC, as well as CBN, CBDV, THCV, CBT, CBG, and other minor cannabinoids as bulk ingredients for global supply chains. All PPM extracts, concentrates, and isolates are tested extensively by accredited third-party labs to be clean, pure and identically chiral (read on) to Nature.

Why do we care about CBC’s Right and Left-Handedness?

Naturally derived CBC is one of the rare cannabinoids that is very versatile with many potential health benefits. During the cannabis plant’s life, CBG converts and produces CBC in two different forms by means of an activated enzyme process. These two different CBC molecules are called chiral isomers or enantiomers and have different three-dimensional structures on the carbon atom that is called the stereocenter.

It is like your right hand and your left hand. While they look the same, the fingers of the left hand are opposite of the right hand. They are also called “non-superimposable” mirror images.

CBC is a chiral phytocannabinoid that is typically reported as a rare case of a natural racemate, meaning both enantiomers are present in the plant in equal ratios.

This means that CBC’s two isomers could interact differently with the endocannabinoid receptors. But as of today, in clinical animal trials, it is the mixture of these two naturally derived cannabinoids that is studied for their biological activity and physiological properties. More studies are needed to determine if it is both isomers that are bioactive or just one of the two, or if they work together synergistically through the entourage effect.

Chemistry 101 – Chirality 

Chirality is a property of asymmetry important in several branches of science. The word chirality is derived from the Greek χειρ (kheir), “hand,” a familiar chiral object.

An object or a system is chiral if it is distinguishable from its mirror image. It can’t be superimposed onto it. A chiral object and its mirror image are called enantiomorphs (Greek, “opposite forms”) or, when reffering to molecules, enantiomers. A non-chiral object is called achiral (sometimes also amphichiral) and can be superposed on its mirror image.

Human hands are perhaps the most universally recognized example of chirality. No matter how the two hands are oriented, it is impossible for all the major features of both hands to coincide in all ways.

Chirality in a naturally occurring molecule means that one enantiomer of a chiral drug may be a medicine for particular disease whereas another enantiomer of the molecule may be not only inactive but can also be toxic.

The classic example of why chirality is critical is the powerful drug called thalidomide that was prescribed to pregnant women in Germany in the 60’s to treat nausea and morning sickness. When the women gave birth, their children had severe teratogenic defects. This is when the pharmaceutical industry started paying attention and realized that chiral drugs need to be separated because as in this case one enantiomer treated morning sickness while the other caused devastating birth defects. This incident also started a multi-billion dollar industry in pharmaceutical chiral separation. Thalidomide has now made a comeback for AIDS and leprosy patients.

Without chemists, who would have thought that right-handed or left-handed is not just relevant in sports? It is absolutely mission critical as the concept relates to health and wellness products made from plants, synthetic drug design, testing, and hemp and its portfolio of bioactive phytochemicals.

A big shout out of THANKS to the global scientific community for building our foundation of knowledge which current and future scientists can take to the next level with minor cannabinoids using the advanced technology equipment and testing instrumentation that is now available.

The Research on CBC

Part II of this Newsletter on CBC, its Chiral Nature and its ECS engagement will provide a basic literature review with links to the published research. Stay Tuned.

What Makes PPM Unique:

PPM is led by a team of advanced-degreed scientists with pharmaceutical industry and university research backgrounds representing over 100 years of chemistry and plant medicine experience.

PPM is committed to advancing the science and providing innovative true whole hemp plant extracts with fully customizable cannabinoid profiles, and minor and rare cannabinoid-based ingredients, both 100% hemp-derived and biosynthesized from hemp plant precursors versions including CBN, CBC, CBT, CBDA, THCV, CBDV, etc. to leading consumer product supply chains worldwide.

Clean. Consistent. Compliant.

Krystle Jarrett
[email protected]