A9—tetrahydrocannabinol

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... 

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... 

Synthesis of A9-Tetrahydrocannabinol from Natural Cannabidiol (Semisynthetic A9-THC)... 

A serious problem in the early Western medicinal use of C. sativa, mainly as a tincture, was its highly variable activity and inconsistent results. Medicinal preparations have to handle several particularities due to the structure of the active ingredients of C. sativa. The identity of the main active constituent of C. sativa, A9-tetrahydrocannabinol (INN dronabinol) remained unknown until 1964 [128] standardized C. sativa preparations were not available. The plant itself is found in several different chemotypes, which added to the unpredictable nature of early medicinal preparations. 

Spector S, Lancz G. Suppression of human macrophage function in vitro by A9-tetrahydrocannabinol. J Leukocyte Biol 1991 50 423 426. 

Chen, J., Paredes, W., Lowinson, J.H., and Gardner, E.L., A9-Tetrahydrocannabinol enhances presyn-aptic dopamine efflux in the medial prefrontal cortex, Eur. J. Pharmacol., 190, 259, 1990. 

Chen J, Paredes W, Li J, Lowinson J and Gardner EL (1990a). A9-tetrahydrocannabinol produces naloxone-blockade enhancement of presynaptic basal dopamine efflux in nucleus accumbens of conscious, freely-moving rats as measured by intracerebral microdialysis. Psychopharmacology, 102, 156-162. 

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). 

Marijuana (reefer, pot, grass, weed) is the most commonly used illicit drug. The principal psychoactive component is A9-tetrahydrocannabinol (THC). Hashish, the dried resin of the top of the plant, is more potent than the plant itself. Pharmacologic effects begin immediately and last 1 to 3 hours. 

Bloom, A. S. (1982) Effect of A9-tetrahydrocannabinol on the synthesis of dopamine and norepinephrine in mouse brain synaptosomes. J. Pharmacol. Exp. Ther., 221 97-103. 

Welch, B. L., Welch, A. S., Messiah, F. S., and Berger, H. J. (1971) Rapid depletion of adrenal epinephrine and elevation of telencephalic serotonin by (-)trans-A9-tetrahydrocannabinol in mice. Res. Commun. Chem. Pathol. Pharmacol., 2 382—391. 

Figure 16.4. Quantification of A9-tetrahydrocannabinol (9THC) after TFA and 11-nor-9-carboxy-A9-tetrahydrocannabinol (THCCOOH) after PFP in blood using GC-MS/NCI. Drug-free blood was spiked with 9THC (a) and THCCOOH (b) to the concentrations of 0, 5, 10, and 50 or 20ng/mL and with ISs-9THC-D3 and THCCOOH-D3 to 20ng/mL. Monitoring ions were (m/z) 410.3 for 9THC and 572.3 for THCCOOH. The values of validation parameters, expressed in ng/mL, were LOD, 0.25 LOQ, 0.5 limit of linearity, 0.5 to 100 for both analytes [2].

M. Kala, M. Kochanowski. The Determination of A9-Tetrahydrocannabinol (9THC) and 11-nor-9-Carboxy-A9-Tetrahydrocannabinol (THCCOOH) in Blood and Urine Using Gas Chromatography Negative Ion Chemical Ionisation Mass Spectrometry (GC-MS-NCI), Chemical Analysis (Warsaw), 51, 2006. 

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-... 

The primary psychoactive ingredient in cannabis, A9-tetrahydrocannabinol ( 9- ), affects the brain mainly by activating a specific cannabinoid receptor, CBj. CB receptors are expressed at high levels in many brain regions, and they are primarily... 

Neuropharmacologic classification of addictive drugs by primary target (see text and Table 32-1). DA, dopamine GABA, 7-aminobutyric acid GHB, 7-hydroxybutyric acid GPCRs, G protein-coupled receptors THC, A9-tetrahydrocannabinol. 

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. 

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