3.24 Chemistry of Cannabis

3.24.1 An Introduction to the Cannabis Plant 1034 3.24.1.1 The Different Forms of Cannabis 1035 3.24.1.2 The Botany of Cannabis sativa 1035 3.24.1.3 A Short History of Cannabis 1037 3.24.1.4 Chemical Constituents of Cannabis 1038 3.24.2 Cannabinoids 1039 3.24.2.1 Cannabinoids Defined 1040 3.24.2.2 Biosynthesis of the Cannabinoids 1041 3.24.2.2.1 The acidic cannabinoids 1041 3.24.2.2.2 Occurrence of short-chain cannabinoids and other homologues 1043 3.24.2.3 A Phytochemical Classification of Cannabinoids 1043 3.24.2.4 Chromatographic Analysis of Cannabinoids 1045 3.24.2.4.1 Decarboxylation 1046 3.24.2.4.2 Microscopy 1046 3.24.2.4.3 Color reactions 1046 3.24.2.4.4 Thin-layer chromatography 1046 3.24.2.4.5 Gas chromatography 1046 3.24.2.4.6 High-performance liquid chromatography 1047 3.24.2.4.7 Other techniques 1047 3.24.2.4.8 Spectroscopic and chromatographic data 1048 3.24.3 Sites and Mechanisms of Action of Cannabinoids 1049 3.24.3.1 The Cannabinoid Receptors: CB1 and CB2 1049 3.24.3.2 The Endocannabinoid System 1050 3.24.3.3 Pharmacokinetics of the Cannabinoids (ADME) 1052 3.24.3.4 Structure–Activity Relationships of Cannabinoids 1053 3.24.3.4.1 An alkyl substituent at C-3 1054 3.24.3.4.2 A hydroxyl substituent at C-1 1054 3.24.3.4.3 The substituent at C-9/C-11 1054 3.24.3.4.4 An aliphatic hydroxyl at C-6 1054 3.24.3.5 Administration Forms 1054 3.24.4 Biological Effects of the Cannabinoids 1055 3.24.4.1 Delta-9-Tetrahydrocannabinol 1056 3.24.4.2 Cannabidiol 1057 3.24.4.3 Delta-8-Tetrahydrocannabinol 1058 3.24.4.4 Cannabigerol 1058 3.24.4.5 Cannabinol 1059 3.24.4.6 Cannabichromene 1059 3.24.4.7 Tetrahydrocannabivarin 1059 3.24.4.8 The Acidic Cannabinoids 1059 3.24.5 Noncannabinoid Constituents of Cannabis 1060 3.24.5.1 Terpenoids 1060 3.24.5.1.1 Biosynthesis and composition of Cannabis essential oils 1061 3.24.5.1.2 Biological activities of terpenoids 1061