Tag Archives: Interest

Pesticide Remediation by CPC

By Arpad Konczol, PhD
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Like any other natural product, the biomass of legal cannabis can be contaminated by several toxic agents such as heavy metals, organic solvents, microbes and pesticides, which significantly influence the safety of the end products.

Let’s just consider the toxicological effects. Since cannabis products are not only administered in edible forms but also smoked and inhaled, unlike most agricultural products, pesticide residue poses an unpredictable risk to consumers. One example is the potential role of myclobutanil in the vape crisis.

Unfortunately, federal and state laws are still conflicted on cannabis-related pesticides. Currently, only ten pesticide products have been registered specifically for hemp by the U.S. Environmental Protection Agency. So, the question arises what has to be done with all pf the high-value, but also contaminated cannabis, keeping in mind that during the extraction processes, not only the phytocannabinoids get concentrated but the pesticides as well, reaching concentrations up to tens or hundreds of parts per million!

Currently, there are three different sets of rules in place in the regulatory areas of Oregon, California and Canada. These regulations detail which pesticides need to be monitored and remediated if a certain limit for each is reached. Because the most extensive and strict regulations are found in Canada, RotaChrom used its regulations as reference in their case study.

Centrifugal Partition Chromatographic (CPC) system

To illustrate that reality sometimes goes beyond our imagination, we evaluated the testing results of a THC distillate sample of one of our clients. This sample contained 9 (!) pesticides, of which six levels exceeded the corresponding action limits. The most frightening, however, regarding this sample, is that it contained a huge amount of carbofuran, a category I substance. It is better not to think of the potential toxicological hazard of this material…

The CPC-based purification of CBD is a well-known and straightforward methodology. As the elution profile on the CPC chromatogram of a distillate shows, major and minor cannabinoids can be easily separated from CBD. At RotaChrom, this method has been implemented at industrial-scale in a cost effective and high throughput fashion. In any case, the question arises: where are the pesticides on this chromatogram? To answer this, we set ourselves the goal to fully characterize the pesticide removing capability of our methodologies.

Our results on this topic received an award at the prestigious PREP Conference in 2019. The ease of pesticides removal depends on the desired Compound of Interest.

Here is a quick recap on key functionalities of the partition chromatography.

  • Separation occurs between two immiscible liquid phases.
  • The stationary phase is immobilized inside the rotor by a strong centrifugal force.
  • The mobile phase containing the sample to be purified is fed under pressure into the rotor and pumped through the stationary phase in the form of tiny droplets (percolation).
  • The chromatographic column in CPC is the rotor: cells interconnected in a series of ducts attached to a large rotor
  • Simple mechanism: difference in partition

Let’s get into the chemistry a bit:

The partition coefficient is the ratio of concentrations of a compound in a mixture of two immiscible solvents at equilibrium. This ratio is therefore a comparison of the solubilities of the solute in these two liquid phases.

The CPC chromatogram demonstrates the separation of Compounds of Interest based on their unique partition coefficients achieved through a centrifugal partition chromatography system.

CPC can be effectively used for pesticide removal. About 78% of the pesticides around CBD are very easy to remove, which you can see here:

In this illustration, pesticides are in ascending order of Kd from left to right. CBD, marked with blue, elutes in the middle of the chromatogram. The chart illustrates that most polar and most apolar pesticides were easily removed beside CBD. However, some compounds were in coelution with CBD (denoted as “problematic”), and some compounds showed irregular Kd-retention behavior (denoted as “outliers”).

If pesticides need to be removed as part of THC purification, then the pesticides that were problematic around CBD would be easier to remove and some of the easy ones would become problematic.

To simulate real-world production scenarios, an overloading study with CBD was performed, which you can see in the graph:

It is easy to see on the chromatogram that due to the increased concentration injected onto the rotor, the peak of CBD became fronting and the apparent retention shifted to the right. This means that pesticides with higher retention than CBD are more prone to coelution if extreme loading is applied.

To be able to eliminate problematic pesticides without changing the components of the solvent system, which is a typical industrial scenario, the so-called “sweet spot approach” was tested. The general rule of thumb for this approach is that the highest resolution of a given CPC system can be exploited if the Kd value of the target compounds fall in the range of 0.5-2.0. In our case, to get appropriate Kd values for problematic pesticides, the volume ratio of methanol and water was fine-tuned. Ascending mode was used instead of descending mode. For the polar subset of problematic pesticides, this simple modification resulted in an elution profile with significantly improved resolution, however, some coelution still remained.

In the case of apolar pesticides, the less polar solvent system with decreased water content in ascending mode provided satisfactory separation.

Moreover, if we focus on this subset in the three relevant regulatory areas, the outcome is even more favorable. For example, myclobutanil and bifenazate, dominant in all of the three regulatory regions, are fully removable in only one run of the CPC platform.

Based on these results, a generic strategy was created. The workflow starts with a reliable and precise pesticide contamination profile of the cannabis sample, then, if it does not appear to indicate problematic impurity, the material can be purified by the baseline method. However, if coeluting pesticides are present in the input sample, there are two options. First, adjusting the fraction collection of the critical pesticide can be eliminated, however the yield will be compromised in this case. Alternatively, by fine-tuning the solvent system, a second or even a third run of the CPC can solve the problem ultimately. Let me add here, that a third approach, i.e., switching to another solvent system to gain selectivity for problematic pesticides is also feasible in some cases.

In review, RotaChrom has conducted extensive research to analyze the list of pesticides according to the most stringent Canadian requirements. We have found that pesticides can be separated from CBD by utilizing our CPC platform. Most of these pesticides are relatively easy to remove, but RotaChrom has an efficient solution for the problematic pesticides. The methods used at RotaChrom can be easily extended to other input materials and target compounds (e.g., THC, CBG).

Political & Corporate Lobbying Influences Emerge in Cannabis

By Cannabis Industry Journal Staff
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In a press release sent out this morning, a new coalition announced their launch to “end the prohibition, criminalization, and overregulation of cannabis in the United States.” The Cannabis Freedom Alliance (CFA) says their core values include federal descheduling, criminal justice reform, “reentry and successful second chances,” promoting entrepreneurship in free markets and reasonable tax rates.

Who’s Behind the CFA?

The organizations that founded the CFA are Americans for Prosperity (AFP), Mission Green/The Weldon Project, the Reason Foundation, and the Global Alliance for Cannabis Commerce (GACC). Take a look at that list and see if you recognize the names. AFP is a well-known conservative and libertarian political lobbying group founded and funded by the Koch brothers. The Reason Foundation, another Libertarian think-tank and an advocate for prison privatization, also listed the Koch brothers as some of their largest donors in disclosures filed in 2012.

The Koch family business, Koch industries, makes hundreds of billions of dollars a year in the oil and gas industry and has held massive political influence for decades. They regularly donate hundreds of millions of dollars to Republican campaigns. Historically, they’ve played a major role in opposing climate change legislation. They’re widely known as conservative advocates for lower corporate taxes, less social services and deregulation.

Interestingly enough, prominent criminal justice reform advocate Weldon Angelos and rapper Snoop Dogg appear to have joined forces with the Koch-backed group, CFA, following a Zoom meeting where Charles Koch told them he thinks all drugs should be legalized, according to Politico. “We can’t cut with one scissor blade. We need Republicans in order to pass [a legalization bill],” Angelos told Politico. The tie between cannabis legalization and traditional Republican and Libertarian values is obvious: their free market, personal liberties and small government ideology fits well within the legalization movement.

Big Oil, Alcohol and Tobacco, Oh My!

The Coalition for Cannabis Policy, Education and Regulation (CPEAR) is a group that was founded in March 2021. Two of the founding members are Altria, the company that makes Marlboro cigarettes, and Molson Coors, a multinational alcohol company. The CPEAR website says that they want to work on responsible federal reform. “We represent a vast group of stakeholders — from public safety to social equity — focused on establishing a responsible and equitable federal regulatory framework for cannabis in the United States.”

Founding members of CPEAR also include: The Brink’s, a private security firm, the National Association of Convenience Stores, the Council of Insurance Agents & Brokers and the Convenience Distribution Association. In other words, the group is made up of large and powerful corporate interest groups that represent the alcohol, tobacco, insurance and security industries.

Both NORML and the Drug Policy Alliance (DPA) have spoken out against CPEAR. Erik Altieri, executive director of NORML, says it’s a matter of corporate interests coming in and working to change laws for their companies to capitalize on legalization. “We’ve seen how big corporate money and influence have corrupted and corroded many other industries,” says Altieri. “We can’t let the legal marijuana industry become their next payday.”

The DPA also released a statement opposing CPEAR. Kassandra Frederique, executive director of the DPA, says that she urges caution to elected officials in taking counsel from these corporate powers. “We have long been concerned about the entry of large commercial interests into the legal marijuana market,” says Frederique. “Big Alcohol and Tobacco have an abysmal track record of using predatory tactics to sell their products and build their brands – often targeting low-income communities of color and fighting public health regulations that would protect people.”

While their motives and desired outcomes remain unclear, it is apparent that we’re reaching a new age in the cannabis legalization movement, one where powerful corporations outside of the cannabis space want in. Whether its oil and gas, insurance, security, tobacco or alcohol, these groups are using their power and money to influence cannabis policy reform.

Cannabis M&A in the Post-COVID Era

By Jose Sariego
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After a slow start following a disappointing 2019, M&A in the cannabis space closed 2020 with a bang, with more than $600 million in deals announced immediately following the November elections. Prospects for the New Year are expected to continue the explosive year-end trend with a backlog of nearly $2 billion in deals heading into 2021. The COVID-19 pandemic boosted sales of cannabis products, and election results opening up five new states to legal cannabis use and possible federal regulatory reform are further boosting prospects. Analysts now predict the U.S. cannabis market is poised to double by 2025.

Growth is expected to be led by multi-state operators who have achieved scale, cleaned up their balance sheets and stockpiled dry powder for roll-up acquisitions. Cannabis companies raised nearly $134 million in the two weeks before Election Day, a 185% increase over the same period last year. Most of the money flowed to multistate operators. In addition, the biggest stocks by market capitalization saw a roughly 20% bump ahead of the election and now are trading at record volumes, providing plenty of stock currency for further acquisitions.

Among the headline acquisitions last year:

  • Curaleaf continued its multi-state expansion with two of its largest acquisitions – the all-stock purchases of its affiliated cannabis oil company Select and of Grassroot, another MSO player. Curaleaf is now the largest cannabis company in the world based on annualized revenues, with annualized sales of $1 billion and operations in 23 states and 96 open dispensaries. Curaleaf also raised $215 million privately last year end for further expansion.
  • Close behind, Aphria and Tilray announced in December that they will merge, creating what they say will be the largest cannabis company in the world with an equity value of roughly $3.8 billion. The combined entity will have facilities and offices in the U.S., Canada, Portugal and Germany. The deal is expected to close during the second quarter of this year.
  • Also in December, Illinois-based Verano Holdings LLC unveiled plans to go public at a $2.8 billion valuation through a reverse takeover of a Canadian shell company. That deal followed the announcement that Verano will merge with Florida-based AltMed.
  • In addition, publicly traded New York cannabis firm Columbia Care signed a definitive agreement last month to acquire Green Leaf Medical, a privately held Maryland-based cannabis manufacturer and retailer, for $45 million in cash and $195 million in stock. The acquisition is expected to close this summer. Including Green Leaf’s inventory, the Columbia Care will operate 107 facilities, including 80 dispensaries and 27 cultivation and manufacturing facilities. Columbia Care also took advantage of cannabis fever last year by raising $100 million privately.
  • Also in December, Ayr Strategies announced it would acquire Liberty Health Sciences, one of the largest cannabis companies in Florida, for $290 million in stock, as well Garden State Dispensary, a New Jersey marijuana company for $41 million in cash, $30 million in stock and $30 million in the form of a note. This follows Ayr’s $81 million acquisition of an Arizona medical marijuana operator in November. Voters approved marijuana use in Arizona and New Jersey in November.  Ayr has completed a string of acquisitions in Nevada, Massachusetts, Pennsylvania, Arizona, Ohio and, upon the closing of December’s deals, New Jersey and Florida.

Not all cannabis companies will rely on acquisitions, however. Trulieve, as an example, has focused its efforts on Florida and organic growth. It remains to be seen whether a multi-state approach fueled by acquisitions or a single-state organic growth model will prove the more lasting. Growth and profitability in the short term likely will continue to be hampered by limits on economies of scale due to federal restrictions and differing state laws.

In light of the maturing industry and the 2019 bust, the valuation model for acquisitions in the cannabis space is evolving from one based on sales, typically associated with emerging growth industries, to a more mature industry model based on profits or Earnings Before Interest, Taxes, Depreciation, and Amortization (EBITDA). Most cannabis MSOs have stabilized and generate positive EBITDA, which justifies the evolution away from a sales-driven model.

From a legal standpoint, the same limitations that have vexed the cannabis industry for years will continue to challenge deal makers until there is greater clarity on the federal front. Institutional investor reluctance, financial industry constraints, haphazard state regulation and the unavailability of federal forums such as national copyright and trademark registration will continue to be issues for acquirers and their lawyers in the space.

Acquisition agreements will continue to have to address the federal Damocles’ sword should expected relaxation of federal enforcement under the Biden administration and further legislative relief does not materialize as expected. Although the U.S. House in December passed the “Marijuana Opportunity Reinvestment and Expungement Act” (MORE) to remove cannabis from the Controlled Substances Act, the Senate did not take up the bill in 2020 and it will have to be re-introduced in 2021. Notably, the MORE Act does not affect existing federal regulation of cannabis, such as the Food, Drug and Cosmetics Act, under which the FDA has limited the use of CBD in certain products despite hemp being removed from the Controlled Substances Act in 2018.

The cannabis M&A market is moving into a more mature phase, as MSOs will be choosier in their approach rather than continuing the land-grab mentality of years past. Due to improved financial strength, 2021 should see these MSOs continuing to expand their footprints either within existing states or new ones. Although uncertainties abound, further consolidation and expansion through add-on acquisitions is likely to continue apace in 2021, providing plenty of opportunities for deal makers and their lawyers.