This article is part of Digamma Consulting’s five-part series, "The Federal Hemp Phenomenon," which delves deeper into hemp's fascinating chemical and medical significance.
Understanding the history, laws, and future opportunities surrounding cannabinoid compounds, including state recreational cannabis and federal hemp, requires some basic knowledge of their chemistry. Don’t worry; we’ll break it down so that even non-scientists, especially those interested in the regulatory aspects, can grasp the essentials.
What Are Cannabinoids?
Cannabinoids are compounds found in the cannabis plant. They come in different forms and can be categorized into four main types: natural cannabinoid acids, natural cannabinoid neutrals, semi-synthetic cannabinoids, and fully synthetic cannabinoids.
Cannabinoid Acids
These are the compounds produced directly by the cannabis plant. For instance, THC and CBD, which are the most well-known cannabinoids, are initially in their acid forms—THCA and CBDA—within the plant. Think of these acids as the raw ingredients that the plant makes first.
Natural Cannabinoid Neutrals
These cannabinoids are created from cannabinoid acids through a process called decarboxylation. This is a fancy term for a chemical reaction that removes a carbon dioxide molecule, converting THCA into THC and CBDA into CBD. This transformation happens naturally when cannabis is exposed to heat, like when smoking or baking. This conversion, unlike the synthetic ones covered below, occurs in nature when cannabis plant material is exposed to the sun.
Semi-Synthetic Cannabinoids
These are made from natural cannabinoids through human-made chemical reactions. Examples include d8-THC, THC-O-Acetate, and HHC. These cannabinoids are tweaked versions of what the plant makes naturally.
Fully Synthetic Cannabinoids
These compounds are lab-made from petrochemicals rather than natural cannabinoids and do not occur naturally. They are designed to interact with cannabinoid receptors in the body. But unlike natural cannabinoids, these compounds can be dangerous. Some, like the infamous "legal high" products Spice and K2, have caused serious health issues. Although these products are useful in research experiments, humans shouldn't consume them without further safety and toxicity trials.
The Delta Series: A Closer Look
Back in 2014, farmers were excited about hemp as a “new” crop after the Farm Bill law was passed, exempting hemp from the Controlled Substances Act in a pilot program capacity. They primarily focused on CBD, which is non-psychoactive, and its precursor, CBDA. They wanted to avoid d9-THC due to its psychoactive effects and legal restrictions. At that time, the chemistry landscape was simpler, with fewer known transformations between cannabinoids.
Fast-forward to 2022, and there's been a significant change: Since the 2018 Farm Bill extended the pilot programs from 2014 as a legalization standard for all operators, chemists have found ways to convert CBD into Δ8-THC, a psychoactive compound that is not legally restricted like its analog d9-THC. This transformation uses a type of acid called a Lewis acid, which helps rearrange the structure of CBD. This reaction is illustrated in the image above, which shows the double bond rearrangement that distinguishes the delta-series of THC.
Advanced Cannabinoid Chemistry: New Isomers
Another major development in cannabinoid chemistry between 2014 and 2022 was the creation of HHC (HexaHydroCannabinol). This compound was first introduced at a conference in 2017. HHC is similar to THC but has its own unique effects.
The process to create HHC starts with CBD and involves converting it through Δ8-THC, using hydrogen and a metal catalyst. This method is the same as how plant oils are turned into margarine, which is called hydrogenation. In this process, the double bond in the delta-series is simply removed from the molecule altogether, turning any member of the delta-series into HHC.
Exploring Pentyl Tail Analogues
Traditional cannabinoids like THC, CBD, and CBG have a five-carbon tail, known as a pentyl tail. When swapping this tail for a three-carbon tail, we get new compounds like THCV, CBDV, and CBGV. Replacing it with a seven-carbon tail gives us THCP, CBDP, and CBGP. These changes can significantly alter the cannabinoids' properties and effects.
For instance, THCV is known for suppressing appetite, unlike THC, which stimulates it. The inverse is true, with THCV being non-psychoactive compared with THC. THCP, on the other hand, binds more strongly to cannabinoid receptors than THC, potentially making it more potent and with a longer duration. These variations are shown in the image above, illustrating how small structural changes can lead to big differences in effects. This is often because the similarity in the rest of the structure guarantees the binding to the cannabinoid receptor, but these small changes can reverse whether the effect is agonistic (positive) or antagonistic (negative) at that receptor.
Why Does This Matter? Especially in the federal hemp phenomenon?
Understanding these chemical transformations is crucial for grasping the legal and regulatory challenges of cannabinoid production and distribution. Different forms of cannabinoids have different legal statuses and implications for the cannabis and hemp industries. On a federal level, all of these cannabinoids discussed here are legal hemp products because they comply with the 2018 Farm Bill’s 0.3% d9-THC. This has created a functional loophole in the federal laws prohibiting psychoactive cannabinoids and has encouraged a large industry of “recreational hemp” products, which are far more profitable due to taxes, safety testing, and other overhead than traditional natural dispensaries. Knowing the chemistry helps navigate these complexities and can inform better business and regulatory decisions.
Next week, in part four of Digamma Consulting's five-part blog series “The Federal Hemp Phenomenon,” we'll explore the legal landscape of cannabinoids and how their chemical properties influence regulations and business practices in the cannabis and hemp industries. Stay tuned for more insights into the fascinating world of cannabinoid chemistry and its real-world implications!
For a copy of the white paper delving even deeper into the phenomenon of hemp, click here.
See this article on our sister site at the Emerald Community: https://community.emeraldscientific.com/the-federal-hemp-phenomenon-part-three-the-chemistry-of-hemp-a-simple-guide/
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