CBD hydroxyquinone photo-isomerises to a highly reactive intermediate.

The legalisation of hemp has led to wide commercial availability of cannabidiol (CBD)-containing products. Here we show that the CBD-hydroxyquinone (HU-331), a readily formed oxidation product and common impurity in CBD isolates, undergoes a previously unknown photo-isomerisation to produce a highly reactive intermediate in solution. Studies supported by calculations indicate that this intermediate rapidly reacts with oxygen to form a multitude of cannabinoid products. The purple colour observed in light-aged CBD-containing solutions is largely due to the anions of these by-products and is not significantly due to the HU-331 anion. Our findings suggest that these uncharacterized cannabinoid derivatives can be present in CBD-containing e-liquids and solutions that have been stored under ambient light conditions, calling for quality control processes that manage HU-331 contamination.

Simulations of Test Reduction Using Pooled Heavy Metals Analysis in Cannabis.

BACKGROUND: Cannabis species have a propensity to bioaccumulate toxic heavy metals from their growth media. Increased testing for these metals is required to improve the safety of the legal medical and recreational cannabis industries. However, the current methods used for mandated heavy metals tests are not efficient for a large framework. As a result, there is limited testing capacity, high testing costs, and long wait times for results across North America. OBJECTIVE: This study aimed to demonstrate that pooling strategies can be used to increase the throughput in cannabis testing labs and reduce some of the strain on the industry. METHODS: This paper presents an algorithm to simulate different pooling strategies. The algorithm was applied to real world data sets collected from Washington and California state testing labs. RESULTS: Using a single pooling method, a pool size of three samples on average resulted in a 23.8% reduction in tests required for 100 samples for the Washington lab. For the California lab, pooling four samples on average resulted in a 54.1% reduction in tests required for 100 samples. CONCLUSION: The algorithms generated from the Washington and California lab data demonstrated that pooled testing strategies can be developed on a case-by-case method to reduce the time, effort, and costs associated with heavy metals tests. HIGHLIGHTS: The benefits of pooled testing will vary depending on the region and rate of contamination seen in each testing lab. Overall, our results demonstrate pooled testing has the potential to reduce the fiscal costs of testing through increased efficiency, allowing increased testing, leading to greater safety.

A Randomized, Triple-Blind, Comparator-Controlled Parallel Study Investigating the Pharmacokinetics of Cannabidiol and Tetrahydrocannabinol in a Novel Delivery System, Solutech, in Association with Cannabis Use History.

Background: An oral route of administration for tetrahydrocannabinol (Δ9-THC) and cannabidiol (CBD) eliminates the harmful effects of smoking and has potential for efficacious cannabis delivery for therapeutic and recreational applications. We investigated the pharmacokinetics of CBD, Δ9-THC, 11-OH-THC, and 11-nor-9-carboxy-Δ9-THC (THC-COOH) in a novel oral delivery system, Solutech™, compared to medium-chain triglyceride-diluted cannabis oil (MCT-oil) in a healthy population. Materials and Methods: Thirty-two participants were randomized and divided into two study arms employing a comparator-controlled, parallel-study design. To evaluate the pharmacokinetics of Δ9-THC, CBD, 11-OH-THC, and THC-COOH, blood was collected at pre-dose (t=0) and 10, 20, 30, and 45, min and 1, 1.5, 2, 2.5, 3, 4, 5, 6, 8, 12, 24, and 48 h post-dose after a single dose of Solutech (10.0 mg Δ9-THC, 9.76 mg CBD) or MCT (10.0 mg Δ9-THC, 9.92 mg CBD). Heart rate and blood pressure were measured at 0.5, 1, 2, 4, 6, 8, 12, 24, and 48 h. Relationships between cannabis use history, body mass index, sex, and pharmacokinetic parameters were investigated. Safety was assessed before and at 48 h post-acute dose. Results: Acute consumption of Solutech provided a significantly greater maximum concentration (Cmax), larger elimination and absorption rate constants, faster time to Cmax and lag time, and half-life for all analytes compared to MCT-oil (p<0.001). In addition, cannabis use history had a significant influence on the pharmacokinetic parameters of CBD, Δ9-THC, 11-OH-THC, and THC-COOH. On average, participants with later age of first use had higher Δ9-THC, CBD, and THC-COOH Cmax and later time-to-Cmax and half-life for Δ9-THC, CBD, THC-COOH, and 11-OH-THC than those with earlier age of first use (p≤0.032). Those with more years of recreational cannabis use had higher area under the curve for Δ9-THC and CBD, Cmax for CBD, and longer 11-OH-THC half-life than those with less (p≤0.048). Conclusion: This study demonstrated that consumption of Solutech enhanced most pharmacokinetics parameters measured compared to MCT-oil. Participant's cannabis use history, including their age of first use and number of years using cannabis significantly impacted pharmacokinetic parameters investigated. Acute consumption of both products was found to be safe and well tolerated. The results suggest that Solutech may optimize bioavailability from cannabis formulations.

Healthy and Concentrated Cannabis Plants: How to Use Acronyms to Optimize Production.

In an industry that has only recently and slowly moved out of the shadows of illegality, regulations and guidelines for cannabis product safety are just catching up to the standards of other industries. Often, our industry has had to introduce best practices and self-regulation to ensure the safety of our products and customers, as well as to help any regulating body in building such frameworks. This article will focus on how OutCo has implemented Hazard Analysis and Critical Control Point (HACCP) protocols to ensure the safety of every aspect of the production pipeline. The prevention of mold growth in drying flowers would be a classic example of food safety and is our prime example of how HACCP has informed our approach to this task. HACCP also contributed to the prevention of pesticide contamination, worker safety, and cannabis oil formulation.

Enantioselective allylic thioetherification: the effect of phosphoric acid diester on iridium-catalyzed enantioconvergent transformations.

You'll take the high road and I'll take the low road: Enantioenriched allylic thioethers have been synthesized from chiral racemic allylic alcohols. The combination of an Ir-(P,alkene) complex and dibutyl phosphoric acid are required to attain high selectivities. Mechanistic studies uncover an enantioconvergent transformation in which substrate enantiomers react along different pathways to give the same product (see scheme; cod=1,5-cyclooctadiene).

Direct, enantioselective iridium-catalyzed allylic amination of racemic allylic alcohols.

The direct route: iridium-catalyzed direct conversion of branched allylic alcohols into enantioenriched branched primary allylic amines is highly regio- and enantioselective.

Stereospecific substitution of allylic alcohols to give optically active primary allylic amines: unique reactivity of a (P,alkene)Ir complex modulated by iodide.

A stereospecific allylic amination of unactivated secondary (secondary)-allylic alcohols is reported. The primary (primary)-allylic amine can be isolated directly or protected in situ. Spectroscopic studies have shed light on the structure of the catalytically active Ir x (P,olefin)2I complex.