Cannabis Tetrahydrocannabinol

Figure 30-29 Structures of the active components of cannabis, tetrahydrocannabinol, and cannabidiol, and structures of endogenous cannabinoids and of the vanilloid lipid capsaicin.

Cannabis is by far the most commonly used illicit drug. Most people who abuse hard drugs such as heroin also abuse cannabis. Tetrahydrocannabinol (acid and A -metabolite) is regulated in the German traffic law (see Table 7-1), and amphetamine, opiates (morphine) and cocaine (as benzoylecgonine metabolite) are also mentioned. 

The two G-protein-coupled receptors for Cannabis psychotropic component, A9-tetrahydrocannabinol... 

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). 

The plant Cannabis sativa produces the psychoactive diug A9-tetrahydrocannabinol (THC). Recreationally, THC is consumed in form of marijuana (dried flowers and leaves) or hashish (resin). The cultivation and possession of Cannabis for recreational use is not... 

Dronabinol (tetrahydrocannabinol), the active principle from cannabis and synthetic cannabinoids, nabilone and levonantradol are effective in treating nausea and vomiting in cancer chemotherapy. The mode of action is unclear but appears to involve cannabinoid CBi receptors. Cannabinoids have been shown to reduce acetylcholine release in the cortex and hippocampus, and have been suggested to inhibit medullary activity by a cortical action. Inhibition of prostaglandin synthesis and release of endorphins may also be involved in the antiemetic effect. A review of trials of dronabinol, nabilone or levonantradol concluded that while the cannabinoids were superior to placebo or dopamine receptor antagonists in controlling emesis... 

Endocannabinoids. Figure 1 Chemical structures of the two most studied endocannabinoids, anandamide and 2-arachidonoylglycerol, of Cannabis sativa psychoactive principle, A9-tetrahydrocannabinol, and of the CB-i receptor antagonist/inverse agonist, rimonabant. 

Teesson M, Lynskey M, Manor B, et al The psychometric properties of BSM-IV cannabis use disorders. Brug Alcohol Bepend 68 235—262, 2002 Tsou K, Patrick SL, Walker JM. Physical withdrawal in rats tolerant to delta 9-tetrahydrocannabinol precipitated by a cannabinoid receptor antagonist. Eur J Pharmacol 280 R13-R15, 1995... 

Szirmai M (1995) Total synthesis and analysis of major human urinary metabolites of dl-tetrahydrocannabinol, the principal psychoactive component of Cannabis sativa L. Dissertation, Uppsala University, Sweden... 

Classical cannabinoids (CCs) are tricyclic terpenoid derivatives bearing a benzopyran moiety. This class includes the natural product (-)-delta-nine-tetrahydrocannabinol (Fig. 8, 1) and the other pharmacologically active constituents of the plant Cannabis sativa. 

Several products are derived from the cannabis plant (table 10.1). Hashish and charas are the dried resin exuded from the female flowers. These have the highest content of A9-tetrahydrocannabinol (TFIC) at 10-20% and have the most potent psychoactive effects. Ganja and sinsemilla are the dried tops of the female plants, which averages 5-8%. Marijuana and bhang are derived from the rest of the plant and have the lowest TFIC concentration (2-5%). 

There are approximately 400 chemicals in the cannabis plant, 61 of which are unique and may be called cannabinoids. The most common psychoactive cannabinoid is A9-tetrahydrocannabinol (A9-THC) (Robbers et al. 1996) (figure 10.4). Other psychoactive cannabinoids include A8-tetrahydrocannabinol (A8-THC), ll-hydroxy-A8-tetrahydrocannabinol (11-OH-A9-THC), and 9-nor-9 j8-hydroxyhexahydrocannabinol p-... 

Cutler MG, Mackintosh JH. (1984). Cannabis and delta-9-tetrahydrocannabinol. Effects on elements of social behaviour in mice. Neuropharmacology. 23(9) 1091-97. 

Edgewood studies in the late 1950s had already demonstrated that delta-9 tetrahydrocannabinol, the active principle of Cannabis indica (a weed that grows in the wild - and sometimes in underground hydroponic farms), was not sufficiently potent to become a chemical weapon. Those studies involved the use... 

One such amide present in chocolate is anandamide (N-arachidonoyl-ethanolamine). Anandamide, together with N-oleylethanolamine and N-linoleylethanolamine, bind to a receptor. In the brain which also binds tetrahydrocannabinol, the psychoactive compound in cannabis. Could this explain the addiction ... 

The psychoactive compounds in the hemp plant. Cannabis sativa, are known as cannabinoids the principal one is tetrahydrocannabinol. It is used as a recreational drug either in the form of dried leaves and flowers (cannabis. 

Hemp Cannabis sativa Flowers, leaves Marihuana tetrahydrocannabinol Smoked Sedative Worldwide Origin China... 

There is much interest in the medical applications of Cannabis sativa L. (marijuana). An oral spray consisting of the marijuana constituents, cannabidiol (CBD,19) and A -mzw-tetrahydrocannabinol (THC, 20), has been approved recendy in Canada for the treatment of neuropathic pain associated with multiple sclerosis (MS), and it is possible that this drug will be approved elsewhere in the near future. ... 

The cannabinoid-type psychoactive principles of marijuana Cannabis sativa L.), have been of interest to pharmacologists for many years. The biological characterization of the major euphoriant principle, (—j-A - wr-tetrahydrocannabinol (THC) (20), has led to an understanding of the molecular mechanisms of these compounds, and ultimately enabled the characterization of the cannabinoid receptor This... 

The advances in isolation methods made possible a clarification of the chemistry of cannabis. In 1963, our group reisolated CBD and reported its correct structure and stereochemistry. A year later we finally succeeded in isolating pure A -tetrahydrocannabinol (A -THC), elucidated its structure, obtained a crystalline derivative and achieved a partial synthesis from CBD. Several years later, a minor psychotomimetically active constituent, A -THC, was isolated from marijuana. Whether this THC isomer is a natural compound, or an artifact formed during the drying of the plant, remains an open problem. 

Turner CE, El-Sohly MA, Constituents of Cannabis sativa L. XVI. Possible decomposition pathway of A -tetrahydrocannabinol to atnn moX, J Pleterocycl Chem 16 1667-1668, 1979. 

Biotransformation of (+)- and -)-cis/trans- etheno s to (-f)-verbenone has been achieved by a cell-free system of Cannabis sativa Callus.The (—)- and (+)-verbenone (via verbenol) were the starting materials for the first synthesis of the (—)- and (+)- enantiomers of A -tetrahydrocannabinol. 

The psychological effects of cannabis are due to cannabinoids such as A -tetrahydrocannabinol (THC) which interact with specific cannabinoid receptors in the brain (Devane et al.,1988 Matsuda et al., 1990). The functions of these receptors are not known but high concentrations are present in sensory and limbic areas, and THC also increases dopamine release from the nucleus accumbens and frontal cortex (Tanda et al., 1987) and decreases the release of acetylcholine (Trzepacz, 2000). 

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