Cannabinol/cannabidiol

Chesher GB and Jackson DM (1985). The quasi-morphine withdrawal syndrome Effect of cannabinol, cannabidiol and THC. Pharmacology, Biochemistry and Behaviour, 23, 13-15. 

As shown in Table 2, cocaine concentrations are detected in almost all the studies targeting psychoactive substances or drugs of abuse in the literature, with the exception of Algiers and Serbia, where cannabinoids were found whilst cocaine was not (Tables 3 and 4). In the literature, cannabinoid concentrations are either expressed as A -tetrahydrocannbinol (THC) or as the sum of cannabinol, cannabidiol and THC (known as CBs). 

Fig. 2 Top Cocaine and CBs levels in the metropolitan region of Rome, detected during field campaigns in 2009-2010. COC cocaine, CBs cannabinol + cannabidiol + A -tetrahydrocannabi-nol). BEL Belloni Street, CIP Cipro Street, FRA Francia Boulevard, MLB Montelibretti, CIA Ciampino, CIV Civitavecchia, CEE Colleferro, GUI Guidonia. Bottom Heroin and THC levels in three Spanish cities, detected during field campaigns in 2008...

Fig. 3 Mean, maximum and minimum airborne concentrations of THC and cannabinoids (CBs) at urban and rural locations around the world. CBs sum of cannabinol, cannabidiol and THC...

The main active ingredients of cannabis are cannabinol, cannabidiol and several isomers of tetrahydrocannabinol, of which delta-9-tetrahydro-cannabinol (THC) is probably responsible for most of the psychoactive effects of the various preparations. It is of interest to note that THC does not contain nitrogen in its three-membered ring system. The structure of THC is shown in Figure 15.8. 

Cannabis (A9-THC-COOH) Cannabis (A9-THC, A9-THC-COOH, cannabinol, cannabidiol)... 

Mechoulam, R., Gaoni, Y. Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids. Tetrahedron 1965, 21, 1223-1229. 

The amount of A °-tetrahydrocannabinol and of structurally related, nonpsychotropic compounds (e.g. cannabinol, cannabidiol and cannabidiolic acid) varies considerably. In contrast to the tropical culture forms, H. from European hemp contains little A -tetrahydrocannabinol and much cannabidiol and cannabidiolic acid. 

Table 13.1 shows the average atmospheric concentrations of cocaine, THC, cannabinol, cannabidiol, nicotine, and caffeine in samples collected in Milan, Bari, and Taranto. Milan is in northern Italy, while Bari and Taranto are in the south, the three cities having different drug consumption patterns (Cecinato et al., 2009a). In Milan, measurements were repeated from June 2006 to Febmary 2007 in order to explore the variability over time. The ratio of cocaine to benzo[a]pyrene (CO/BaP) is also reported to illustrate the relationship between illicit substances and other anthropogenic pollutants. 

Group of compounds which naturally occur in the hemp plant, Cannabis saiiva. Most of them are unsoluble in water. The most abundant cannabinoids are A9--tetrahydrocannabinol (THC), its precursor cannabidiol and cannabinol, which is formed spontaneously from THC. Cannabinoids exert their effects through G-protein coupled cannabinoid receptors (CBi/CB2). 

Oxidation of the phenol ring of cannabidiol (73) or cannabinol to a qui-none ring has been shown to afford compounds with anti-tumour activity. However, these compounds do not bind to the CBi receptor and their mechanism of action is unclear [128],... 

There are over 400 constituent compounds in marijuana. More than 60 of these are pharmacologically active cannabinoids, of which 4 are the most important. The most psychoactive is delta-9-tetrahydrocannabinol (A-9-THC). The other three important natural cannabinoids are A-8-THC, cannabinol and cannabidiol (Kumar et al., 2001). In addition, some of the metabolites of THC, such as 11-hydroxy-A-9-THC, are also psychoactive. As a consequence and contrary to many other drugs, the metabolism of THC in the liver does not decrease intoxication, rather it prolongs it. 

A few studies have been conducted on cannabis and its derivatives. Alozie et al. (3) measured the radioactivity accumulated in various brain areas following the intravenous injection of 3H-THC, 3H-cannabinol, and 3H-cannabidiol to adult male rats. Five minutes after injection, these three labeled compounds exhibited a homogeneous distribution in brain, suggesting that no specific binding occurred. Such studies must be completed by examining the time course of the evolution of 3H-cannabis derivatives in various brain areas before any firm conclusion can be drawn. 

HHC) (Tripathi 1987). Unless stated otherwise, THC will be used to refer to A9-THC throughout the remainder of this chapter. Other cannabinoids that are not psychoactive include cannabinol and cannabidiol. More recently, endogenous substances have been identified that activate these receptors, and are referred to collectively as endocannabinoids (table 10.2). 

Gas chromatography coupled to tandem mass spectrometry (GC-MS/MS [49]) prior to analysis of the three primary active components of cannabis (THC, cannabidiol and cannabinol) by this technique, airborne particulates were extracted in an ultrasonic bath with chloroform. The extracts were combined and concentrated under a stream of nitrogen. The residue was filtered through pre-washed disposable PTFE membranes, dried and finally reconstituted with cyclohexane. After separation and solvent partitioning, the extracts were analysed by GC-MS/MS. 

Until the mid 1960 s the only plant cannabinoid whose structure was fully elucidated was cannabinol (CBN) — a constituent which actually may represent an oxidation artifact. However, on the basis of CBN, the main cannabinoid structure skeleton became known. Thus, cannabidiol (CBD), which had been independently isolated in pure form by Adams and by Todd, was correctly assumed to be, like CBN, a terpenoid derivative attached to olivetol. But its exact structure was not elucidated. The psychoactive components of cannabis were assumed to be related tricyclic derivatives. On the basis of the tentatively elucidated constituents, Todd suggested that the cannabinoids may be formed initially in the plant by condensation of a menthatriene with olivetol. 

A second cannabis constituent, cannabidiol (CBD) was also isolated, but its structure was only partially clarified. Synthetic tetrahydro-cannabinols, which showed cannabis-like activity in animal tests, were prepared, but they obviously differed from the active natural product, on the basis of their UV spectrum. 

Jacob A, Todd AR, Cannabis indica. Part 11. Isolation of Cannabidiol from Egyptian Hashish. Observations on the Structure of Cannabinol, J Chem Soc... 

Adams R, Pease DC, Cain CK, Baker BR, Clark JH, Wolff H, Wearn RB, Conversion of cannabidiol to a product with marihuana activity. A type reaction for synthesis of analogous substances. Conversion of cannabidiol to cannabinol, J Amer Chem Soc 62 2245—2246, 1940. 

Cannabis chinensis Del. C. sativa L. Huo Ma Ren or Da Ma Ren (Hemp) (fruit, seed) Vitamin Bj, vitamin B2, muscarine, choline, trigonelline, l(d)-isoleucine betaine, cannabinol, tetra-hydrocannobinol, cannabidiol.33-450 Purgative, stimulate intestinal mucosa causing an increase in secretions and peristalsis. 

At least 60 bioactive compounds are contained in herbal cannabis. A9-Tetrahydrocannabinol (A9-THC) (Mechoulam and Gaoni, 1967), cannabidiol and cannabinol are the major psychoactive or adjuvant ingredients. Cannabinoids act through at least two different G-protein coupled receptors named CBi and CB2 receptors. 

Among the long list of diverse structures reported to possess central antitussive activity is Ahtetrahydrocannabinol (THC) [1972-08-3] (68), the principal psychoactive component of marijuana (see PSYCHOPHARMACOLOGICALAGENTS). This compound was found to be comparable to codeine against electrically induced cough in the anesthetized cat (90). Two other naturally occurring cannabinoids, cannabidiol and cannabinol, are inactive. 

More than 400 chemical compounds have been identified in marijuana. Approximately 60 of these are unique to the cannabis plant, substances called cannabinoids. Of the cannabinoids, a group of isomers (chemically similar substances) called tetrahydro-cannabinols (THC) are thought to be the most psychoactive. These are Ai-THC (also called A9-THC) and A6-THC (also called A8-THC). Other cannabinoids include cannabidiolic acid (CBDA), cannabidiol (CBD), and cannabinol (CBN). Their role in marijuana intoxication is less well understood. The amount of THC produced depends on the strain of cannabis and on environmental factors such as growth, harvest, and storage conditions. 

The psychoactive and medicinal chemical compounds found in the resin of the marijuana plant are known as cannabinoids. The cannabis plant contains more than 460 known compounds over 60 of these have a cannabinoid structure. The only cannabinoid that is highly psychoactive and present in large amounts in the resin of the cannabis plant is tetrahydrocannabinol, or THC. The other two major cannabinoids are the cannabidiols and the cannabinols. It appears that the cannabis plant first produces the mildly active cannabidiols, which are converted to the more psychoactive THCs and then broken down to relatively inactive... 

Phytocannabinoids are natural compounds present in Cannabis sativa, responsible for the pharmacological and toxicological properties of this plant. About 70 compounds belong to this class, the most important are A9-tetrahydrocannabinol (THC), cannabinol (CBN), and cannabidiol (CBD). 

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