9-Tetrahydrocannabinol

The successful isolation and structural elucidation [1147, 1148] of Zl tetrahydrocannabinol (CVII), which is the major active principle of hashish, has at last paved the way for accurate quantitative pharmacological studies in this area, although the absence of animal tests accurately reflecting the CNS-effects 

Preliminary experiments with pure Zl THC have revealed [63, 1147] that it shows an analgesic effect in mice and rabbits and a psychotomimetic action in human beings. Further experiments having bearing on its exact mechanism of action in the CNS are eagerly awaited. 

Up to 65% of the amount consumed is excreted within the first 5 days, and detection of a single consumption of hashish is possible for 12 days by determination of metabolites in the urine. After high-dose or regular consumption of the drug, THC metabolites may often be found in the urine for up to 4 weeks. 

Suitable immunological reagents for the detection of cannabis abuse from urine tests are available from several companies. In normal circumstances, the sensitivity of a test corresponds to a cut-off value of 50 ng/ml based on 11-nor-A9-THC-9-carboxylic acid. The cut-off values of some cannabinoids are listed in Table 8-29. Only U-nor-A9-THC-9-carboxylic acid is relevant to the determination of consumption from urine tests. 

Hemp (Cannabis saliva L.) belongs among the oldest cultivated plants (Fig. 5.64). Originally native to India, Afghanistan and Iran, hemp is now found almost everywhere in the world, at times even in our allotments and in balcony cultivation. 

The utilisation of hemp as a source of fibres was known in China for at least 4,800 years. Also the Egyptians had used it, as documented by texts dating back to the end of the Fifth Dynasty (ca. 2350 BC), carved in pyramid stones, and hemp fibres were found in the tomb of Amenhotep IV (alias Akhenaten or Echnaton, ca.1334 BC). [119] The Greeks encountered hemp only in the 5th century BC 

Around the same time Germanic tribes were also cultivating hemp. The Celts had known hemp since the Hallstatt period (700-450 BC). In the 3rd century BC, the Gauls in the Rhone valley used hemp to manufacture ropes and clothing. Hiero II (308-215 BC), the tyrant of Syracuse, Sicily, imported hemp from there for the production of marine ropes. In Roman literature, hemp is first mentioned by Gains LucUius (180-102 BC). 

On a worldwide basis, cannabis is nowadays the most frequently consumed drug. The United Nations Organisation estimates that between 2.8 and 4.5 % of 

Global licit production of cannabis grew steadily in the last decade and stabilized at a level of about 6 tonnes. After an increase in 2007 (10 tonnes), the production of cannabis declined to 4-5 tonnes in 2010. In 2011, a sharp rise to almost 25 tonnes were registered. [121] 

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Gannabinoids. Like the BZ receptor, the cannabinoid receptor was initially identified using psychotropic alkaloids such as A -tetrahydrocannabinol (A-THC) (78) that were known to affect mammalian CNS function (see PsYCHOPHARMACOLOGiCALAGENTs). The CNS receptor,... 

A great advantage of catalyst 24b compared with other chiral Lewis acids is that it tolerates the presence of ester, amine, and thioether functionalities. Dienes substituted at the 1-position by alkyl, aryl, oxygen, nitrogen, or sulfur all participate effectively in the present asymmetric Diels-Alder reaction, giving adducts in over 90% ee. The reaction of l-acetoxy-3-methylbutadiene and acryloyloxazolidinone catalyzed by copper reagent 24b, affords the cycloadduct in 98% ee. The first total synthesis of ewt-J -tetrahydrocannabinol was achieved using the functionalized cycloadduct obtained [23, 33e] (Scheme 1.39). 

Terolidine 2, 56 Tesicam T79 Tesimide 296 Testolactone 160 Testosterone cypionate 1, 172 Testosterone decanoate T, 172 Testosterone propionate 1, 172 Tetrabenazine 350 Tetracaine 1, 110 Tetracycline 1, 212 Tetrahydrocannabinol, A-1, 1, 394... 

Roger Adams (1889-1971) wa s born in Boston, Massachusetts, and received his Ph.D. in 1912 at Harvard. He taught at the University of Illinois from 1916 until his retirement in 1957, during which lime he had an enormous influence on the development of organic chemistry in the United States. Among many other accomplishments, he established the structure of tetrahydrocannabinol, the active ingredient in marijuana. 

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. 

A9-Tetrahydrocannabinol (THC) Antidiabetic Drugs AMP-activated Protein Kinase Adipokines PPARs... 

The tetrahydrocannabinol carboxylic acid was extracted from the urine by means of a solid state extraction cartridge packed with a Cl 8 reverse phase (octyldecyldimethyl chains). As the urine sample was used direct, and contained no added solvent, the materials of interest were irreversibly adsorbed on the reverse phase solely by dispersive interactions. 

Compton WM, Grant BF, Colliver JD, et al Prevalence of marijuana use disorders in the United States 1991-1992 and2001-2002. JAMA291 2114-2121,2004 Cook SA, Lowe JA, Martin BR CBl receptor antagonist precipitates withdrawal in mice exposed to delta9-tetrahydrocannabinol. J Pharmacol Exp Ther 285 1150— 1156, 1998... 

Lepore M, Vorel SR, Lowinson J, et al Conditioned place preference induced by delta-9-tetrahydrocannabinol comparison with cocaine, morphine, and food reward. LifeSci 56 2073-2080, 1995... 

Lichtman AH, Sheikh SM, Loh HH, et al Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice. J Pharmacol Exp Ther 298 1007—1014, 2001... 

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... 

Wachtel SR, El Sohly MA, Ross SA, et al Comparison of the subjective effects of deltaO-tetrahydrocannabinol and marijuana in humans. Psychopharmacology... 

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