Prediction and Discovery of Cannabidiol Crystal Polymorph Form 2.

The article puts into perspective the recent discovery of cannabidiol crystal polymorph Form 2.

Luminescence enhancement by deuterium.

Created literally at the dawn of time, deuterium has been extremely valuable in so many chemistry roles. The subject of this review focuses on one deuterium application in particular: its enhancement of luminescence in many substances. After providing general overviews of both deuterium and luminescence, the early exploration of deuterium's effect on luminescence is described, followed by a number of specific topics. These sections include a discussion of deuterium-influenced luminescence for dyes, proteins, singlet oxygen, and the lanthanide elements, as well as anomalous inverse deuterium luminescence effects. Future directions for this important research topic are also proposed, as well as a summary conclusion.

Delta-9-Tetrahydrocannabinolic Acid B: A Mechanism for its Formation in Cannabis.

There appears to be consensus among Cannabis biologists that delta-9-tetrahydrocannabinolic acid A (THCA-A) is the exclusive product of the enzyme THCA synthase. This then leaves an open question for formation of the THCA-A structural isomer, delta-9-tetrahydrocannabinolic acid B (THCA-B), discovered as a minor product in Cannabis in 1969. With no reasonable biochemical pathway to explain the presence of THCA-B in Cannabis, a synthetic route was next considered. Using established literature precedent, a photochemical mechanism has been proposed for the conversion of THCA-A to cannabidiolic acid (CBDA), followed by conversion of CBDA to THCA-B employing bond-breaking and bond-forming reactions.

Cannabinoid Photochemistry: An Underexplored Opportunity.

Photochemistry is a powerful synthetic tool resulting in the construction of unique substances. Remarkably, photochemistry has been relatively underexplored in the cannabinoid area and represents a valuable opportunity for further discovery.

Radiolabelling of bisphenol A and several related analogues.

This paper describes the synthesis and characterization of bisphenol A and several closely associated derivatives with 14C and tritium.

Cannabinoid crystal polymorphism.

Because cannabinoids are usually amorphous solids, the thought that some of them may also exist in distinctly different crystal polymorphic forms might at first seem unusual. However, this commentary provides compelling evidence and precedent for the likely existence of cannabinoid crystal polymorphism.

A synthesis of [14 C]formamidine acetate.

The one-step synthesis of [14 C]formamidine acetate from [14 C]barium cyanamide is described with product characterization by TLC and proton NMR.

Acidic Cannabinoid Decarboxylation.

Introduction:Cannabis is a valuable plant, cultivated by humans for millennia. However, it has only been in the past several decades that biologists have begun to clarify the interesting Cannabis biosynthesis details, especially the production of its fascinating natural products termed acidic cannabinoids. Discussion: Acidic cannabinoids can experience a common organic chemistry reaction known as decarboxylation, transforming them into structural analogues referred to as neutral cannabinoids with far different pharmacology. This review addresses acidic and neutral cannabinoid structural pairs, when and where acidic cannabinoid decarboxylation occurs, the kinetics and mechanism of the decarboxylation reaction as well as possible future directions for this topic. Conclusions: Acidic cannabinoid decarboxylation is a unique transformation that has been increasingly investigated over the past several decades. Understanding how acidic cannabinoid decarboxylation occurs naturally as well as how it can be promoted or prevented during harvesting or storage is important for the various stakeholders in Cannabis cultivation.

MicroED and cannabinoid research.

MicroED has recently emerged as a convenient and powerful tool for the unequivocal structure determination of small molecules and it could likely be used in cannabinoid research as well.

Tritium labelling of two potent dopamine D2 receptor agonists at high specific activity.

An efficient method is described to radiolabel several dopamine D2 receptor agonists with tritium at high specific activity.

Chirality in Cannabinoid Research.

Mankind has long utilized Cannabis for diverse purposes. However, it has only been since the late 19th century that its individual cannabinoids began to be isolated, analyzed, and synthesized. By the mid-20th century it was discovered that many cannabinoids were asymmetric, with chirality often controlling their pharmacology. Increasingly accurate measurement and understanding of cannabinoid chirality will facilitate their synthesis and accelerate their medicinal applications.

An effective and scalable 14C radiolabelling of several biogenic indole derivatives at high specific activity.

An efficient method is described to radiolabel several biogenic indole derivatives with carbon-14 at high specific activity.

S-(4-nitrobenzyl)-6-thioinosine: Tritium labelling at high specific activity.

The one-step tritiation of S-(4-nitrobenzyl)-6-thioinosine is described with characterization of the product by tritium NMR as well as mass spectrometry. The storage, stability, and repurification of [benzyl methylene-3 H]S-(4-nitrobenzyl)-6-thioinosine are also discussed.