Tetrahydrocannabinol compounds

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). 

This compound and its related acidic form, A8-tetrahydrocannabinolic acid (A8-THCA, 2.13) are structural isomers of A9-THC. Although it is the thermodynamically stable form of THC, A8-THC (2.14) contributes approximately only 1% to the total content of THC in C. sativa. In the synthetic production process, A8-THC is formed in significantly higher quantities than in plants. 

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. 

Kupfer D, Levin E and Burstein SH (1973). Studies on the effects of tetrahydrocannabinol and ddt on the hepatic microsomal metabolism of the and other compounds in the rat. Chemical-Biological Interactions, 6, 59-66. 

As it can be observed in Fig. 2, three out of the 16 investigated compounds, namely, heroin, lysergic acid diethylamide (LSD), and its metabolite 2-oxo, 3-hydroxy-LSD (O-H-LSD), were not detected in any wastewater sample. Two other target analytes, 6-acetyl morphine (6ACM) and A9-tetrahydrocannabinol (THC), were only present in influent wastewaters and with low detection frequencies. The most ubiquitous compounds, present in all influent and effluent wastewater samples analyzed, were the cocaine metabolite benzoylecgonine, and the amphetamine-like compounds ephedrine (EPH) and 3,4-methylenedioxymethamphetamine (MDMA or ecstasy). Cocaine, cocaethylene (CE, transesterification product of cocaine formed after the joint consumption of cocaine and ethanol), and morphine (MOR) were detected in all influent, but not in all effluent wastewaters (see Fig. 2). 

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. 

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. 

A -3,4-cis-THC has now been found in Cannabis sativa (Phenotype III) other papers reporting the characterization of compounds from Cannabis sativa concern conclusive identification and synthesis of cannabinodiol, " which is known to result from the photochemical irradiation of cannabinol (Vol. 7, p. 51), and the identification of A -tetrahydrocannabinolic acid " and (+)-cannabitriol (263) " (263) and the corresponding C-2 ethyl ether may be epoxide-derived. " ... 

Cannabis sativa plants contain at least 400 different compounds, of which as many as 60 are structurally related to 5 -tetrahydrocannabinol (5 -THC), the primary psychoactive constituent of cannabis. When cannabis is smoked, hundreds of additional compounds are produced by pyrolysis, which may contribute to both acute and chronic effects (Abood and Martin, 1992). The central nervous system actions of canna-binoids are mediated primarily through the CBj receptor. A second type of cannabinoid receptor, termed the CB2 receptor, is distributed primarily in the periphery (Gifford et ah, 1999). Activation of central cannabinoid receptors modulates neurotransmitter release at... 

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. 

Cannabinoids are the psychoactive components of marijuana, which has the species name Cannabis sativa. Concentrations of cannabinoids vary greatly from plant to plant. The original strains of this plant species contain very little of these psychoactive components and have been used for many centuries for their great fiber qualities. Strains of Cannabis that may be smoked for psychoactive effects on average contain about 4 percent cannabinoid derivatives. The most active of these derivatives is the compound A9-tetrahydrocannabinol (THC), shown in Figure 14.33 on page 504. 

A9-Tetrahydrocannabinol (A9-THC) is considered to be the predominant compound in preparations of C. sativa (marijuana, hashish, bhang) that is responsible for the central nervous system effects in humans. The recognized central nervous system responses to these preparations include alterations in cognition and memory, euphoria, and sedation. Potential therapeutic applications of cannabis preparations that are of either historical or contemporary interest include analgesia, attenuation of the nausea and vomiting of cancer chemotherapy, appetite stimulation, decreased intestinal motility of diarrhea, decreased bronchial constriction of asthma, decreased intraocular pressure of glaucoma, antirheumatic and antipyretic actions, and treatment of convulsant disorders. These effects have been reviewed recently (Howlett, 1995). 

TETRAHYDROCANNABINOLS (THC) A group of cannabinoid compounds thought to cause most of the psychoactive reactions to marijuana use. 

The active principle of Salvia divinorum, salvinorin A, is derived from the leaves of the plant. Chemically, salvinorin A is a neoclerodane diterpene, one of a group of nitrogen-containing terpene compounds that have psychotropic properties. Two other such compounds are tetrahydrocannabinol and absinthe. Purified salvinorin A can be obtained from an ether extract of the leaves, which is then concentrated by chromatography and repeated crystallization. 

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