Recent Advances in the Science of Cannabis

Description

Recent Advances in the Science of Cannabis describes progress in a variety of significant areas of cannabis science. This unique book covers topics in cultivation and secondary metabolites, aroma and chemotypes, cannabinoid structures, physiology and pharmacology, as well as the development of unique topical products. State-of-the-art analytical methods and instrumentation are covered, including current developments in mass spectrometry and chromatography, as well as microbial testing. Given the popularity of smoking and vaporizing cannabis, the chemistry of vaping cannabinoid and terpene concentrates is also presented, along with emerging regulatory issues.  Key Features: A guide to emerging modern cannabis technology in a dynamic regulatory climate and appealing to both novices and specialists. Building upon pioneering studies of terpene and cannabinoid chemistry, this distinctive volume describes current best practices, technological breakthroughs and historical context. Written by researchers in industry and academia, a greater understanding of the risks of exposure to emissions from vaping or dabbing cannabis concentrates is provided here. A selection of the book content reviewing Thermal Degradation of Cannabinoids and Cannabis Terpenes has been included in “Hot 2021” RSC Advances. Cover Half Title Title Page Copyright Page Table of Contents Preface Editors Contributors Chapter 1 Cultivation Stress Techniques and the Production of Secondary Metabolites in Cannabis sativa 1.1 Introduction 1.2 What are Secondary Metabolites? 1.2.1 Types of Secondary Metabolites 1.2.1.1 Phytocannabinoids 1.2.1.2 Terpenes/Terpenoids 1.2.1.3 Flavonoids 1.2.2 Why Secondary Metabolites Are Produced 1.2.3 Metabolic Pathways for Production 1.3 Cultivation 1.3.1 Genetic Potential 1.3.2 Indoors vs Outdoors 1.3.3 Reproduction and Propagation Techniques 1.4 Types of Stresses 1.4.1 Biotic 1.4.1.1 Microbes, Arthropods, and Herbivores 1.4.1.2 Space and Competing Plants 1.4.1.3 Physical Damage 1.4.2 Abiotic 1.4.2.1 Light Stress 1.4.2.2 Carbon Dioxide 1.4.2.3 Drought 1.4.2.4 Thermal Stress 1.4.2.5 Nutrition, Salts, and Heavy Metal Stress 1.5 Other Factors 1.5.1 Time of Harvest 1.5.2 Drying and Curing Process 1.6 Summary Bibliography Chapter 2 Aroma in Cannabis: A Foundation for Chemotype Classification 2.1 Introduction 2.1.1 The Linguistics of Aroma 2.1.2 Terpenoids 2.2 Identifying Cannabis Aroma Categories Based on Terpenoid Content 2.2.1 The 2015 Golden Tarp Awards Competition 2.2.2 Multivariate Analyses of Terpenoids and Aroma Groups 2.3 Validating Cannabis Aroma Categories Using The Dosing Project™ 2.3.1 Cannabis Aroma Category Response Rates Correlate with the Annual Commodity Production Cycle 2.3.2 Cannabis Aroma Category Preferences by Height: A Surrogate for Gender 2.4 Identifying Biochemical Markers that Define Cannabis Aroma Categories 2.5 Summary and Future Directions 2.5.1 Summary 2.5.2 Future Directions 2.6 Acknowledgments Abbreviations Bibliography Chapter 3 Cannabinoid Chemistry of Cannabis 3.1 Introduction 3.2 The Chemistry Behind Cannabinoids 3.2.1 Biosynthesis 3.2.2 Decarboxylation 3.2.3 Oxidation 3.2.4 Isomerization 3.3 Cannabinoids 3.3.1 One-Ring Type 3.3.1.1 Biogenic Compounds 3.3.1.2 Compounds Formed by Heat 3.3.2 Bridged Two-Ring Type 3.3.2.1 Biogenic Compounds 3.3.2.2 Compounds Formed by Heat 3.3.2.3 Thymyl-Type Compounds 3.3.3 Three-Ring[6,6,6] Type 3.3.3.1 Biogenic Compounds 3.3.3.2 Compounds Formed by Heat 3.3.3.3 Aromatic Products of Oxidation 3.3.3.4 Hydroxylated Products of Oxidation 3.3.4 Two-Ring[6,6] Type 3.3.5 Four-Ring[5,4,6,6] Type Cannabinoids 3.3.6 Three-Ring[6,5,6] Type 3.3.7 Miscellaneous Cannabinoids 3.3.7.1 Unusual Structures 3.3.7.2 Epoxides and Esters 3.4 Conclusion References Chapter 4 Use of Mass Spectrometry for the Analysis of Cannabis sativa spp. 4.1 Introduction 4.1.1 Cannabis and Cannabinoids 4.1.2 Gas Chromatography 4.1.3 Liquid Chromatography 4.1.4 Mass Spectrometry 4.2 Cannabinoid Analysis by Gas Chromatography-Mass Spectrometry 4.3 Cannabinoid Analysis by Liquid Chromatography-Mass Spectrometry 4.4 Cannabinoid Analysis by Mass Spectrometry 4.5 Conclusions References Chapter 5 New Trends in the Analysis of Cannabis-Based Products 5.1 Introduction 5.2 Analysis of Cannabis Products: Analyte Classes 5.2.1 Cannabinoids 5.2.1.1 Analysis of ∆9-Tetrahydrocannabinol and Other Psychoactive Cannabinoids 5.2.1.2 Analysis of Non-Psychoactive Cannabinoids 5.2.2 Analysis of Other Specialised Metabolites 5.2.3 Contaminants 5.2.3.1 Herbicides and Other Pesticides 5.2.3.2 Heavy Metals 5.3 Conclusion Bibliography Chapter 6 Cannabis Microbial Testing: Methodologies and Considerations 6.1 Introduction 6.2 Types of Cannabis Microbiological Testing: Total Counts and Pathogens 6.3 The Role of Water Activity in Microbial Growth 6.4 State Regulations for Water Activity 6.5 Total Count Tests and Their Thresholds 6.5.1 Total Yeast and Mold 6.5.2 Total Aerobic Count 6.5.3 Total Coliforms 6.5.4 Bile Tolerant Gram-Negative 6.6 Pathogens of Interest in Cannabis and Cannabis Products 6.6.1 Aspergillus 6.6.2 Salmonella spp. 6.6.3 Shiga-Toxin Producing E. Coli 6.7 Other Potential Organisms of Concern 6.7.1 Botrytis cinerea 6.7.2 Fusarium spp. 6.7.3 Listeria spp. 6.7.4 Legionella 6.7.5 Rhizopus, Mucor, and Rhizomucor 6.7.6 Powdery Mildew 6.8 Methodology: Culture-Based vs. Molecular 6.9 Contaminant Confirmation Using MALDI-TOF-MS 6.10 Insights from the Cannabis Microbiome 6.11 Cultivation Practices That Reduce Harmful Contaminants: The Plight of Organic Growers 6.12 The Importance of Representative Sampling 6.13 To Enrich or Not to Enrich? 6.14 Microbial Remediation Techniques 6.15 Microbial Considerations for Cannabis Extracts 6.16 Solvent Polarity: Why It Matters 6.17 Extraction Solvents 6.17.1 Ice and Cold Water 6.17.2 Hydrocarbons 6.17.3 CO2 6.17.4 Ethanol 6.18 Additional Concerns for Cannabis Extraction: Mycotoxins and Other Contaminants 6.19 Distillation: A Work Around 6.20 Reference Methods and Standardization 6.20.1 American Herbal Pharmacopeia 6.20.2 Association of Official Agricultural Chemists 6.20.3 European Pharmacopoeia 6.20.4 United States Pharmacopeia 6.21 Concluding Statements References Chapter 7 Cannabis Extract Formulations and Devices 7.1 Safety Considerations for Cannabis Concentrates Meant for Inhalation 7.2 Molecules Found Naturally Occurring in Cannabis 7.3 Flavor Additives 7.4 Diluents and Non-Flavor Additives 7.5 Vaping Devices and User Behavior 7.6 Quality Control and Testing 7.7 Conclusion References Chapter 8 Transdermal Delivery 8.1 Introduction 8.2 Overview of the Skin 8.2.1 Structure and Function of the Skin 8.2.2 Existence of the Endocannabinoid System in the Skin 8.3 Cannabis Extracts and Physicochemical Properties 8.3.1 Cannabis Extract Forms 8.3.2 Stability Challenges with Cannabis Extract 8.3.3 Physicochemical Properties of Phytocannabinoids 8.4 Fundamentals of Topical Formulation and Development 8.4.1 Advantages of Topical Cannabis Products 8.4.2 Emulsions and Excipients 8.4.3 Chemical Penetration Enhancers 8.5 Differences in Skin and Cannabis Use Among Biological Sexes 8.5.1 Biological Sex Skin Differences 8.5.2 Biological Sex Differences of Cannabis Intake and Effects 8.6 Vaginal Delivery and Considerations 8.6.1 Introduction and History 8.6.2 Drug Delivery System in Biologically Sexed Female Reproductive Organs 8.6.3 The Endocannabinoid System in Biologically Sexed Female Reproductive Organs 8.6.3.1 ECS and Pregnancy 8.6.3.2 ECS and Cancer 8.6.4 Safety: Ingredients and Dosage 8.6.5 Drug Product Design 8.6.5.1 Oil-Based Suppositories 8.6.5.2 Creams and Salves 8.6.5.3 Oil vs. Water-Based Lubricants 8.6.6 Future of Vaginally Administered Products 8.7 Conclusion Bibliography Chapter 9 Thermal Degradation of Cannabinoids and Cannabis Terpenes: A Review 9.1 Introduction 9.2 Thermal Reactivity of the Cannabinoids 9.3 The Reactivity of Myrcene, a Prevalent Cannabis Terpene 9.4 Cannabis Vaping Chemistry: Background 9.5 The Chemistry of Terpene Dabbing 9.6 THC and Terpene Vaping Chemistry 9.7 THC and Myrcene Reaction Synergy and Mechanisms 9.8 Conclusion References Chapter 10 Cannabis Pharmacokinetics and Pharmacodynamics 10.1 Introduction 10.2 Pharmacokinetics of Cannabinoids 10.2.1 Absorption of Cannabinoids 10.2.2 Distribution of Cannabinoids 10.2.3 Metabolism of Cannabinoids 10.2.4 Elimination of Cannabinoids 10.3 Pharmacokinetic Models of Cannabinoids 10.3.1 Pharmacokinetic Modeling of THC and Metabolites 10.3.2 Pharmacokinetic Modeling of CBD and Metabolites 10.3.3 Significance and Development of a Unified THC Model 10.3.4 Pharmacokinetic Model for THC and Metabolites Including Elimination 10.3.5 Modeling Urine Flow Rate and Void Volume using NHANES Data 10.3.6 Model Evaluation 10.4 Pharmacodynamics of Cannabinoids 10.4.1 Endocannabinoidome and Endocannabinoid Signaling 10.4.2 Localization of Cannabinoid Receptors 10.5 Organism-Level Effects of Cannabinoids 10.5.1 Effects of Cannabis on Driving Skills 10.5.2 Association of THC and Heart Attacks 10.5.3 Anxiolytic Effects of CBD 10.6 Conclusions References Index