Without oversight of hemp products, delta-8-THC, other cannabinoids flourish in unregulated market
glowing CBD sign hangs in the store window. Inside are an array of products claiming to contain cannabinoids derived from hemp.
But the products for sale go far beyond nonintoxicating cannabidiol (CBD), known for its calming, antianxiety, and pain relief properties. Psychoactive chemicals like ∆8-tetrahydrocannabinol (delta-8-THC) and hexahydrocannabinol are for sale in gummies, tinctures, vaping oils, and other products intended to be ingested or inhaled.
Also for sale are products that have nothing to do with hemp. Some are analogs of delta-9-THC, the main ingredient in cannabis responsible for making users high. These chemicals differ only in the length of the molecule’s carbon chain. The longer the chain, the more psychoactive—up to about eight carbons. Beyond eight carbons, the psychoactivity starts to decrease. Products containing tetrahydrocannabiphorol (THCP) and tetrahydrocannabioctyl (THCjd), which have a seven-carbon and an eight-carbon chain, respectively, are more intoxicating than delta-9-THC, which has a five-carbon chain.
Companies that produce hemp-derived cannabinoids are also acetylating THC and THCP, making THC-O-acetate and THCP-O-acetate. These chemicals are potentially 100 times as psychoactive as delta-9-THC, warns Christopher Hudalla, president and chief scientific officer of ProVerde Laboratories, an analytical testing firm.
“It actually gets very scary with some of the modifications they’re doing. There’s no thought to consumer safety,” Hudalla says. People who have eaten THCP-O-acetate gummies claim they were nonfunctional for 3 days, he says.
Some people say these emerging cannabinoids are exempt from the US Controlled Substances Act because they are made from hemp. But not all these products could possibly come from hemp, Hudalla argues. “There’s no way you can make THCP from hemp,” he says.
Hudalla explains that a cannabinoid with a seven-carbon tail can be synthesized only from a starting material with a seven-carbon tail. Hemp contains no chemical with a seven- or eight-carbon tail in any significant quantity, he says. THCP and THCjd are synthesized from commercial chemicals, he emphasizes.
Shops that sell intoxicating products under the guise of “hemp derived” are prevalent throughout the US. Unlike cannabis products sold in state-regulated marijuana dispensaries, these are not subject to quality and safety requirements.
Chemists like Hudalla have been sounding the alarm about contaminantsin delta-8-THC products for several years. In the absence of federal regulations, they say the contamination problem has gotten worse and—with the proliferation of new cannabinoids—more urgent. “We see new structures all the time. There are 400 structures I’ve identified that might be in the consumer market,” Hudalla says.
Delta-8-THC is typically made from CBD. The process involves heating pure CBD in an organic solvent with a strong acid. Delta-8-THC is often considered a milder intoxicant than delta-9-THC. The only difference between them is the location of a double bond between two carbons. The chemical itself is unlikely to pose a safety risk, but contaminants and unintended reaction by-products are raising concerns.
Hudalla and colleagues have tested thousands of delta-8-THC items, including gummies and vape cartridges. They all contained by-products and impurities, he says. For some products, unintended cannabinoids made up as much as 40% of the total cannabinoids, according to Hudalla. Many of them do not exist naturally in cannabis and carry no safety information.
Some of those by-products are cannabinoids that are hard to identify using standard methods like high-performance liquid chromatography (HPLC) because their retention times and ultraviolet absorbance are similar to that of delta-8-THC, says Mark Scialdone, an organic chemist and founder of BetterChem Consulting, which specializes in the fine chemical and cannabis industries.
Two cannabinoids—∆8-iso-THC and ∆4(8)-iso-THC—are often confused with delta-8-THC when labs use HPLC, leading them to overestimate the amount of delta-8-THC in a product. But the three compounds can be distinguished by gas chromatography, Scialdone says. The R&D firm Cayman Chemical has even developed reference standards for the two iso THC compounds to help commercial labs analyze delta-8-THC products.
One of the newer cannabinoids on the scene is hexahydrocannabinol (HHC). It is less common than delta-8-THC, but it is widely available online and increasingly showing up in vape shops. HHC can be synthesized from delta-8- or delta-9-THC. The reaction involves hydrogenation to remove the double bond in THC. It requires hydrogen gas, which is flammable, and metal catalysts, which can leave behind toxic metals.
Recent research by chemists at the University of California, Los Angeles, suggests that the R isomer of HHC has similar bioactivity to delta-9-THC but that the S isomer does not (ACS Chem. Biol. 2023, DOI: 10.1021/acschembio.3c00254). HHC products on the market are a mixture of the two isomers, and the amount of each varies widely, the researchers report.
HHC isomers were first synthesized in the 1940s, but until the UCLA study there was little information about their binding affinity to cannabinoid receptors and bioactivity in the human body.
“The compounds have been tested in animals before, but the basic binding assays of each isomer were somehow not done or not reported,” study author Neil Garg, an organic chemist at UCLA, says in a press release. “That is unusual for a product that’s widely available to consumers, and it reflects the need for more fundamental research in this rapidly evolving field.”
The surge in synthetic cannabinoids began in 2018, when Congress legalized hemp in the farm bill. At the time, lawmakers were focused on unleashing the CBD market and giving farmers a new cash crop.
Major food and beverage manufacturers were anxious to start adding CBD and other hemp-derived ingredients to their products. But shortly after passage of the 2018 farm bill, the US Food and Drug Administration declared that it is illegal to add CBD to food and beverages or to sell it as a dietary supplement.
Continue at: https://cen.acs.org/biological-chemistry/natural-products/Waiting-CBD-regulations-US/101/i28
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