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  • Cannabeginners: What are Cannabis Alkaloids? | High Times

    Cannabeginners: What are Cannabis Alkaloids? | High Times


    What does cannabis, coca leaf, and all coffee have in common? They all contain alkaloids, a powerful group of medicinal compounds found in plants around the world. While little is presently known about cannabis alkaloids, they are suspected to possess impressive medical benefits like other plant alkaloids. 

    Alkaloids vs. Cannabinoids

    Alkaloids are “one of the most common groups of chemicals that [have] medicinal properties found in plants,” commonly used alkaloids include “morphine, cocaine, nicotine, caffeine, quinine, ephedrine, and many more.” They derive their name, alkaloid, from the word alkali, chemicals that react like bases, counteracting acids. Usually found in the outer tissues of plants, the bitter flavor of alkaloids is believed to be a natural defense in plants to prevent them being eaten by herbivores, similar to cannabinoids and terpenes which both assist in preventing predation. 

    While cannabinoids like THC, CBD, CBG, and THCv, are oily, lipohpilic (binds to fats), and hydrophobic (do not bind to water) compounds, alkaloids are a very different class of chemicals. The biggest chemical difference between alkaloids and cannabinoids is that all alkaloids include a nitrogen atom which binds to additional hydrogen atoms. Cannabinoids, on the other hand, do not have any nitrogen atoms and contain a chain of carbon atoms, which gives them their oily character. 

    Courtesy Duke University

    Despite their differences, efficient methods to extract both alkaloids and cannabinoids from plants is to simply burn the leaves or other parts that contain the chemicals, or perform a chemical extraction. These methods have been used for thousands of years for both types of chemicals; the caffeine in coffee is chemically extracted by brewing with water, cannabis is smoked, and cocaine was originally extracted through chewing or brewed as a tea. 

    Discovery of Alkaloids in Cannabis

    Cannabis is a very complicated plant and “more than 500 compounds have been reported from C. sativa, of which 125 cannabinoids have been isolated and/or identified as cannabinoids.” Non-cannabinoid constituents of cannabis include “42 phenolics, 34 flavonoids, 120 terpenes and 2 alkaloids.” Though, there is some debate over the number of alkaloids which have been identified.

    The discovery of alkaloids in cannabis actually manages to predate the discovery of the first cannabinoid, CBN, back in 1896, by more than a decade. In 1881, the first research on the alkaloid cannabinine was presented at the British Pharmaceutical Conference, and two years later another physiologically active alkaloid, tetanocannabin, was discovered. Cannabis alkaloid research then remained dormant until the 1970s.

    In 1971, a group of scientists isolated four different alkaloids from cannabis, which they named cannabimines A-D. In 1975, two teams of researchers at the University of Mississippi (UMiss) identified and isolated the first spermidine alkaloid, cannabisativine, from the roots, leaves, and stems of both Mexican and Thai cultivars. The next year, the same researchers at UMiss isolated the second spermidine alkaloid, anhydrocannabisativine and showed that cannabisativine could be converted to anhydrocannabisativine. 

    While the cannabis alkaloids cannabisativine and annhydrocannabisativine were first discovered in Mexican and Thai cultivars, anhydrocannabisativine has since been “found in plant samples of Cannabis from 15 different geographical locations.”

    Which Part of The Plant Has the Most Alkaloids?

    Just like how not every part of a cannabis plant has the same amount of cannabinoids, alkaloids are also unequally distributed around the plant. Research has repeatedly shown that, “cannabis roots are not a significant source of cannabinoids or the aforementioned terpenes, but are rich in other compounds, including … alkaloids.” So while terpenes and cannabinoids are concentrated primarily in the trichomes on the leaves, cannabis alkaloids are primarily found in the roots (but can be found in the stems and leaves as well). 

    Medical Effects of Cannabis Alkaloids

    While cannabis alkaloids have a lot of medical potential, the specifics of that potential are unknown. In the case of cannabisativine and anhydrocannabisativine, “no pharmacological information is available,” but it is believed that “there are several compounds in cannabis root with potential anti-inflammatory activity, including alkaloids.” 

    Other researchers have noted that, as a class of compounds, “alkaloids may be used as analgesics, antibiotics, anticancer drugs, antiarrhythmics, asthma medications, antimalarials, anticholinergics, bronchodilators, laxatives, miotics, oxytocics, vasodilators, psychotropics, and stimulants,” and that likely includes cannabis alkaloids. One study of cannabis alkaloids found them to “have diuretic, analgesic, anticancer, antipyretic, and antiemetic effects.”

    In one study, a petroleum ether solution of cannabis alkaloids and cannabinoids had “a course of action comparable to that of atropine,” a drug commonly given to reduce fluid in the respiratory tract during surgery, which “can also treat insecticide or mushroom poisoning.” It is not clear to what extent those observed effects were due to the alkaloids or the cannabinoids. 

    A Quick Hit

    Despite being one of the most common groups of medicinal chemicals found in plants, alkaloids are some of the least known chemicals in cannabis. Early research shows that they may have strong medical benefits as part of the entourage of medicinal compounds in cannabis. 



    Mitchell Colbert

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  • Cannabeginners: CBD for Sleep | High Times

    Cannabeginners: CBD for Sleep | High Times

    One of the most common reasons why people use cannabis or hemp products is for help with sleep. Those who are looking for help sleeping but want to avoid feeling high generally assume CBD will help them sleep without any intoxication, but actually, depending on the dose of CBD they take, it could make it even harder to get to sleep.

    The Discovery and History of CBD

    Though cannabinol (CBN) has the honor of being the first cannabinoid ever discovered, CBD was a close second. In 1940, Roger Adams and his colleagues at the University of Illinois first isolated CBN and then later that same year isolated CBD. At that point, little was known about the effects or the chemical structure. 

    It took until 1963, when Raphael Mechoulam elucidated the chemical structure of CBD, one year before elucidating THC. As soon as THC’s intoxicating effects were discovered by Raphael Mechoulam in 1964, CBD was largely ignored, even by the research community. Then in 2008, with the advent of the first cannabis testing lab in the world, CBD was “rediscovered” and has since been the subject of considerable study. 

    CBD for Sleep

    In 1981, one of the earliest studies to explore CBD’s relationship to sleep showed that “Subjects receiving 160 mg cannabidiol reported having slept significantly more than those receiving placebo.” While some of the volunteers in the study used doses lower than 160mg, those lower doses were not reported to have had as strong of a sedating effect. A 2012 literature review summarized the extent of research over the preceding three decades on CBD and sedation, “clinical trials suggest that high-dose oral CBD (150–600 mg/d) may exert a therapeutic effect for social anxiety disorder, insomnia and epilepsy, but also that it may cause mental sedation.” The following year, a study done on rats found those sedating effects applied to rodents as well as humans, with the rodents experiencing increased “total sleep time, in addition to increasing sleep latency.” 

    Most recently, a 2019 study using people rather than rodents, found sleep benefits for some patients, but their data is limited because the dosing was inconsistent. Still, they observed that “Sleep scores improved within the first month in 48 patients (66.7%) but fluctuated over time,” that fluctuation largely happened once patients were receiving outpatient care and consistent dosing became even more difficult. The researchers did not do a good job reporting what dose of CBD corresponded to what benefit for sleep, but they noted the past research that higher doses did result in a longer “duration of sleep.”

    CBD for Alertness

    Astute readers might now be wondering, if the research is pretty consistent that a high dose of CBD, generally over 160 mg of CBD, produces feelings of sedation, what about a lower dose? That is where the science of CBD and sleep gets really complicated, and is a perfect illustration of the biphasic properties of many cannabinoids (where low doses produce one effect, and higher doses produce a radically different response). 

    In 1977, four years before Carlini and Cunha released their study showing high doses of CBD could improve sleep, Monti demonstrated that CBD could cause rats to sleep less. In 2006, Eric Rodríguez led a team of researchers, including Raphael Mechoulam, on a study which expanded on Monti’s research and showed that low doses of CBD “induces alertness” and suggested “it might be of therapeutic value in sleep disorders such as excessive somnolence.” Rodríguez followed up on his study two years later, which showed CBD was “a wake-inducing compound” at low doses. In 2014, Rodríguez did a literature review of CBD’s effects on sleep, which noted “contradictory results on the effect of CBD on sleep,” going back to the earliest days of CBD research. Rodríguez’ literature review pointed to differences in “route of administration, vehicle used, doses, subjects, etc” as a cause for the paradoxically different effects of CBD on sleep and alertness. In a 2019 study on narcolepsy, Rodríguez and his team suggested that “CBD might prevent sleepiness in narcolepsy.”

    What Do Consumers Actually Want?

    Now that we have dug into the research on CBD’s effects on sleep, let’s take a moment to talk about what it is consumers are actually looking for when they are looking for a CBD product to help with sleep. It is important for individuals to ask themselves, “What is it that is preventing me from sleeping?” Is their core issue a lack of sedation, i.e. they can’t get tired? Or is it racing thoughts, pain, or something else that is preventing them from sleeping? The Budtender’s Guide is a wonderful handbook for aspiring budtenders and consumers alike to have a deeper understanding of different cannabis products and the medical effects of cannabis.

    If someone’s core issue is not getting drowsy, in other words, they do not feel tired, then it is likely that they will need a much higher dose of CBD to achieve their desired outcome. If their main problem is pain, racing thoughts, or one of the myriad of other things CBD can help with, they may be able to use a lower dose to achieve their desired results for sleep but they should take their CBD a couple of hours before bed so the alerting effects have some time to wear off.

    Mitchell Colbert

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  • Cannabeginners: Delta-8, Delta-9, Is All THC Created Equal?

    Cannabeginners: Delta-8, Delta-9, Is All THC Created Equal?

    Delta-8-Tetrahydrocannabinol (delta-8, also seen as ∆8-THC) is a psychoactive and intoxicating cannabinoid similar to Delta-9-Tetrahydrocannabinol (the commonly found THC we all know well). Delta-8 has seen a surge in popularity due to a legal loophole in federal regulations that limits THC to 0.3% in hemp products but has no limit for delta-8.

    The History of Delta-8

    Roger Adams and a team of researchers at the University of Illinois were the first to report partial synthesis of delta-8 in 1941. It wasn’t until 1966, when Dr. Raphael Mechoulam and his colleague Dr. Yechiel Gaoni, achieved a total synthesis of delta-8 as part of their groundbreaking work at Hebrew University. In 2002, Dr. Mechoulam applied for a patent on the conversion of CBD into delta-8 and THC through various methods, which he received in 2008, and expired in 2022. As delta-8 is an isomer of THC, they have a similar chemical structure, and the only difference is the location of a double bond between two carbons. They are both psychoactive chemicals with intoxicating, euphoric properties. 

    A year before Dr. Mechoulam’s patent expired was the first time the American Association of Poison Control Centers “introduced a product code specific to delta-8 THC into its National Poison Data System, allowing for the monitoring of delta-8 THC adverse events.” That would mean that, officially, 2020 was the year that the delta-8 craze began in America. 

    Is Delta-8 Natural or Synthetic?

    The answer to this question is complicated and depends on how you define a synthetic cannabinoid. The National Institute on Drug Abuse says that “Synthetic cannabinoids are human-made mind-altering chemicals … they are similar to chemicals found in the marijuana plant.” In order to be synthetic, a cannabinoid must be made by humans and be similar to chemicals found in the plant. In the case of delta-8, it is not similar to a cannabinoid found in the plant, it naturally is found there in very small amounts. Even though the majority of delta-8 on the market is from a lab, not the plant, the cannabinoids were still made by the plant, they were converted by humans. 

    The FDA’s guidance is a little more complicated. While they note delta-8 is “produced naturally by the cannabis plant,” they are clear that “concentrated amounts of delta-8 THC are typically manufactured from hemp-derived cannabidiol (CBD).” As the word “manufactured” is another way of saying something was “made,” it is ambiguous on if the FDA would view delta-8 as synthetic, and it would likely depend on where it was sourced from (a plant versus a lab). 

    How Most Delta-8 Gets Produced

    As there are only trace amounts of delta-8 found in hemp and cannabis plants, an incalculably high percentage of delta-8 on the market was produced in a lab using the chemical conversion that Dr. Mechoulam discovered. 

    The publication Chemical and Engineering News (CEN) described the process as “refluxing CBD in an organic solvent, such as toluene or heptane, with p-toluenesulfonic acid or another acid that serves as a catalyst.” In a controlled, regulated environment, these reactions would be done by PhD chemists to ensure there are no harmful by-products left in products sold to consumers, but the hemp industry is notoriously under-regulated with no requirements for lab testing. Experts who spoke to CEN described the conversion process as “pretty aggressive” and noted that it used “strong acids,” and in order to neutralize those conditions they would need to use strong bases, metal catalysts, or a number of other methods.

    While it is possible to purify converted delta-8 from unwanted contaminants, reaction leftovers, or other by-products, most people doing those conversions are not chemists and do not properly distill it or use appropriate testing methods. 

    Is Delta-8 Dangerous?

    A literature review published last year found that, “No comprehensive review articles have been published that focus exclusively on Δ8-THC,” meaning their study was the first to focus on delta-8. Rather than finding delta-8 to be more harmful than THC, they found “that Δ8-THC has [a] weaker potency than Δ9-THC.”

    Jeffrey Raber, is a cofounder and the CEO of the Werc Shop, a California-based cannabis contract manufacturing and testing firm, who saw the potential of delta-8 several years ago. “It’s a very interesting molecule, one that has very different physiological activity depending upon the entourage,” said Raber, who is urging regulators to address the testing and purity concerns around delta-8 while still allowing safe use.

    The FDA received 104 reports of adverse events in people who used delta-8 products between December 1, 2020, and February 28, 2022. None of those were fatal, and the events included “hallucinations, vomiting, tremor, anxiety, dizziness, confusion, and loss of consciousness.” Poison control centers around the US received 2,362 cases of delta-8 exposure from January 1, 2021 (when delta-8 was first coded) and February 28, 2022, with one pediatric case that resulted in death. 

    What is not clear is if those negative experiences and that one death were caused by delta-8 itself, or the rampant impurities in delta-8 products. Due to the lack of regulations, much of the delta-8 on the market is tainted with trace amounts of other cannabinoids (possibly THC or even Delta-10-THC, another isomer) and by-products from the chemical conversion. 

    Kyle Boyar is a research associate at the Center for Medicinal Cannabis Research, and has reported that olivetol, a chemical precursor to THC, is a common by-product found in delta-8 products, adding “I don’t think anybody really knows the safe inhalation dose of olivetol.” As there are a range of solvents used for the conversion from CBD, there can be a wide variety of residual solvents in delta-8 products, and some, like dichloromethane and trichloroacetic acid, don’t even have standardized testing methods developed. 

    What Caused the Delta-8 Craze?

    While 2020 was the year of the craze, what was the “why” behind the delta-8 craze? Some sources note that the delta-8 craze began only after the price of CBD plummeted, and hemp companies needed a new way to turn a profit. So was a need to stay profitable the reason behind the delta-8 craze?

    It certainly was a contributing factor, but the real cause of the delta-8 craze, like the CBD craze before it, was cannabis prohibition. If there was no cannabis prohibition, then everyone using less safe hemp products could use legal, lab tested cannabis products. As long as whole plant cannabis containing over a certain amount of THC is illegal, people around the world will look for ways to get around that limit and create legal loopholes, and that is all delta-8 is, a new loophole to circumvent prohibition. 

    The post Cannabeginners: Delta-8, Delta-9, Is All THC Created Equal? appeared first on High Times.

    Mitchell Colbert

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