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Tetrahydrocannabinol THC is one of at least cannabinoids identified in cannabis. THC is the principal psychoactive constituent of cannabis. THC, along with its double bond isomers and their stereoisomers \\\\\\\\\\\[13\\\\\\\\\\\] , is one of only three cannabinoids scheduled by the UN Convention on Psychotropic Substances the other two are dimethylheptylpyran and parahexyl. It is specifically still listed under Schedule I by US federal law \\\\\\\\\\\[15\\\\\\\\\\\] under the Controlled Substances Act for having 'no accepted medical use' and 'lack of accepted safety'. THC is an active ingredient in Nabiximols , a specific extract of Cannabis that was approved as a botanical drug in the United Kingdom in as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain , spasticity , overactive bladder , and other symptoms. The presence of these specialized cannabinoid receptors in the brain led researchers to the discovery of endocannabinoids , such as anandamide and 2-arachidonoyl glyceride 2-AG. THC targets receptors in a manner far less selective than endocannabinoid molecules released during retrograde signaling , as the drug has a relatively low cannabinoid receptor efficacy and affinity. In populations of low cannabinoid receptor density, THC may act to antagonize endogenous agonists that possess greater receptor efficacy. Due to its partial agonistic activity, THC appears to result in greater downregulation of cannabinoid receptors than endocannabinoids , further limiting its efficacy over other cannabinoids. THC, as well as other cannabinoids that contain a phenol group, possesses mild antioxidant activity sufficient to protect neurons against oxidative stress , such as that produced by glutamate -induced excitotoxicity. In , cannabidiol was isolated and identified from Cannabis sativa , \\\\\\\\\\\[30\\\\\\\\\\\] and THC was isolated and described for its structure and synthesis in As with many aromatic terpenoids , THC has a very low solubility in water, but good solubility in most organic solvents , specifically lipids and alcohols. A total synthesis of the compound was reported in ; that procedure called for the intramolecular alkyl lithium attack on a starting carbonyl to form the fused rings, and a tosyl chloride mediated formation of the ether. Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme to produce cannabigerolic acid, \\\\\\\\\\\[34\\\\\\\\\\\] which is cyclized by the enzyme THC acid synthase to give THCA. The pathway for THCA biosynthesis is similar to that which produces the bitter acid humulone in hops. THC and its OH-THC and THC-COOH metabolites can be detected and quantified in blood, urine, hair, oral fluid or sweat using a combination of immunoassay and chromatographic techniques as part of a drug use testing program or in a forensic investigation. Recreational use of cannabis is now legal in many parts of North America and it has increased the demand for new platforms for monitoring THC for both personal and law enforcement applications. Breath sampling as a noninvasive method is has shown promising results to detect THC. Scientists and industry researchers are commercializing various types of breath analyzers to monitor THC in breath \\\\\\\\\\\[40\\\\\\\\\\\]. Female cannabis plants contain at least cannabinoids, \\\\\\\\\\\[44\\\\\\\\\\\] including cannabidiol CBD , thought to be the major anticonvulsant that helps people with multiple sclerosis ; \\\\\\\\\\\[45\\\\\\\\\\\] and cannabichromene CBC , an anti-inflammatory which may contribute to the pain-killing effect of cannabis. As of October when recreational use of cannabis was legalized in Canada, some dietary supplements and 19 veterinary health products containing not more than 10 parts per million of THC extract were approved with general health claims for treating minor conditions. The status of THC as an illegal drug in most countries imposes restrictions on research material supply and funding, such as in the United States where the National Institute on Drug Abuse and Drug Enforcement Administration regulated sources of cannabis for researchers until August when licenses were provided to growers for supplies of medical marijuana. In April , the American Academy of Neurology found evidence supporting the effectiveness of the cannabis extracts in treating certain symptoms of multiple sclerosis and pain, but there was insufficient evidence to determine effectiveness for treating several other neurological diseases. From Wikipedia, the free encyclopedia. For other uses, see THC disambiguation. US : C Risk not ruled out. IUPAC name. Interactive image. Further information: Dronabinol. Not to be confused with Droperidol. See also: Effects of cannabis , Long-term effects of cannabis , and Cannabis in pregnancy. For a review of the mechanisms behind endocannabinoid synaptic transmission, see Endocannabinoid system. Main article: Cannabis drug testing. Further information: Medical cannabis. Arts Culture. Edibles Smoking Tea. Drug culture Illegal drug trade Psychedelia. Cannabis portal Chemistry portal. Archived from the original PDF on Retrieved Clin Pharmacokinet. In Sean C. Sweetman ed. Pharmaceutical Press. National Center for Biotechnology Information. Retrieved 12 January April Journal of the American Chemical Society. August Isomerization to Tetrahydrocannabinols'. Oxford: Biology. Journal of the International Hemp Association. Economic Botany. Photochemistry and Photobiology. Chemical Communications. Retrieved 14 January US Food and Drug Administration. September UK Electronic Medicines Compendium. March Government of Canada. Retrieved 19 October Archived from the original on 8 November Retrieved 11 June International Journal of Obesity. British Journal of Pharmacology. Appl Environ Microbiol. Br J Psychiatry. Because they are extremely lipid soluble, cannabinoids accumulate in fatty tissues, reaching peak concentrations in 4—5 days. They are then slowly released back into other body compartments, including the brain. Within the brain, THC and other cannabinoids are differentially distributed. High concentrations are reached in neocortical, limbic, sensory and motor areas. Chem Biodivers. THC is highly lipophilic and initially taken up by tissues that are highly perfused, such as the lung, heart, brain, and liver. Drug Testing and Analysis. Life Science. Handbook of Experimental Pharmacology. Clark Bibcode : Sci FEBS Letters. Journal of Experimental Botany. J Pharm Pharmacol. Clinical Chemistry. Journal of Analytical Toxicology. Disposition of Toxic Drugs and Chemicals in Man 9th ed. Journal of Breath Research. February Archived from the original on Chemical Heritage Newsmagazine. Archived from the original on 19 June World Health Organization. Journal of Natural Products. In Kinghorn, A. Progress in the Chemistry of Organic Natural Products. Springer International Publishing. Multidisciplinary Association for Psychoactive Substances. F; Wolff, R. V; Keurentjes, J. Krishnan S ed. WIN 55, Cannabis plant. Outline of cannabis Recreational and medical applications Industrial applications. Autoflowering cannabis Cannabis indica ruderalis sativa Difference between C. Medical cannabis Cannabis product testing History Medical cannabis research Timeline Religious and spiritual use Chalice. Adult lifetime use by country Annual use by country. Cannabis political parties List of British politicians who have acknowledged cannabis use List of American politicians who have acknowledged cannabis use. Ker v. California Leary v. United States Gonzales v. Raich Kyllo v. Cannabis portal Category. Medical and recreational uses. Recreational drug use. Calea zacatechichi Silene capensis. Coffee break Coffeehouse Latte art Tea house. Abuse Date rape drug Impaired driving Drug harmfulness Effects of cannabis Addiction Dependence Prevention Opioid replacement therapy Rehabilitation Responsible use Drug-related crime Fetal alcohol spectrum disorder Long-term effects of cannabis Neurotoxicity Overdose Passive smoking of tobacco or other substances. Alcohol legality Alcohol consumption Anabolic steroid legality Cannabis legality Annual use Lifetime use Cigarette consumption Cocaine legality Cocaine use Methamphetamine legality Opiates use Psilocybin mushrooms legality Salvia legality. See also: Recreational drug use. Diphenidine Ephenidine Fluorolintane Methoxphenidine. Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan. Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D 2 agonists, such as dopamine reuptake inhibitors cocaine , methylphenidate , releasing agents amphetamine , methamphetamine , and precursors levodopa. Glaucine Isoaminile Noscapine Pukateine. Antiemetics A Dronabinol Nabilone Tetrahydrocannabinol cannabis. Atropine Diphenhydramine Hydroxyzine very mild Hyoscyamine Scopolamine. Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol. Appetite stimulants A Ancient anaesthesia. Acetylcholine metabolism and transport modulators. Inhibitors: Hemicholinium-3 hemicholine Triethylcholine Enhancers: Coluracetam. Inhibitors: Vesamicol. Cannabinoid receptor modulators. Agonists: Revosimeline. Glycine receptor modulators. See here instead. Opioid receptor modulators. TRP channel modulators. Dehydroligustilide celery Nicotine tobacco Ruthenium red. Triptolide Tripterygium wilfordii. Ruthenium red. Xenobiotic-sensing receptor modulators. Hidden categories: CS1 errors: missing periodical CS1 maint: archived copy as title Wikipedia articles needing page number citations from January CS1 maint: multiple names: authors list Drugs with non-standard legal status Articles with changed EBI identifier ECHA InfoCard ID from Wikidata Infobox drug articles with non-default infobox title Articles without KEGG source Drugboxes which contain changes to verified fields Drugboxes which contain changes to watched fields All articles lacking reliable references Articles lacking reliable references from March Namespaces Article Talk. Views Read Edit View history. In other projects Wikimedia Commons. By using this site, you agree to the Terms of Use and Privacy Policy. Mostly hepatic by CYP2C \\\\\\\\\\\[3\\\\\\\\\\\]. Consumption Edibles Smoking Tea. Related Drug culture Illegal drug trade Psychedelia. Cannabis portal Medicine portal Agriculture portal. Activators Triptolide Tripterygium wilfordii.
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Tetrahydrocannabinol THC is one of at least cannabinoids identified in cannabis. THC is the principal psychoactive constituent of cannabis. THC, along with its double bond isomers and their stereoisomers \\\\\\\\\\\\\\\\\\\\\[13\\\\\\\\\\\\\\\\\\\\\] , is one of only three cannabinoids scheduled by the UN Convention on Psychotropic Substances the other two are dimethylheptylpyran and parahexyl. It is specifically still listed under Schedule I by US federal law \\\\\\\\\\\\\\\\\\\\\[15\\\\\\\\\\\\\\\\\\\\\] under the Controlled Substances Act for having 'no accepted medical use' and 'lack of accepted safety'. THC is an active ingredient in Nabiximols , a specific extract of Cannabis that was approved as a botanical drug in the United Kingdom in as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain , spasticity , overactive bladder , and other symptoms. The presence of these specialized cannabinoid receptors in the brain led researchers to the discovery of endocannabinoids , such as anandamide and 2-arachidonoyl glyceride 2-AG. THC targets receptors in a manner far less selective than endocannabinoid molecules released during retrograde signaling , as the drug has a relatively low cannabinoid receptor efficacy and affinity. In populations of low cannabinoid receptor density, THC may act to antagonize endogenous agonists that possess greater receptor efficacy. Due to its partial agonistic activity, THC appears to result in greater downregulation of cannabinoid receptors than endocannabinoids , further limiting its efficacy over other cannabinoids. THC, as well as other cannabinoids that contain a phenol group, possesses mild antioxidant activity sufficient to protect neurons against oxidative stress , such as that produced by glutamate -induced excitotoxicity. In , cannabidiol was isolated and identified from Cannabis sativa , \\\\\\\\\\\\\\\\\\\\\[30\\\\\\\\\\\\\\\\\\\\\] and THC was isolated and described for its structure and synthesis in As with many aromatic terpenoids , THC has a very low solubility in water, but good solubility in most organic solvents , specifically lipids and alcohols. A total synthesis of the compound was reported in ; that procedure called for the intramolecular alkyl lithium attack on a starting carbonyl to form the fused rings, and a tosyl chloride mediated formation of the ether. Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme to produce cannabigerolic acid, \\\\\\\\\\\\\\\\\\\\\[34\\\\\\\\\\\\\\\\\\\\\] which is cyclized by the enzyme THC acid synthase to give THCA. The pathway for THCA biosynthesis is similar to that which produces the bitter acid humulone in hops. THC and its OH-THC and THC-COOH metabolites can be detected and quantified in blood, urine, hair, oral fluid or sweat using a combination of immunoassay and chromatographic techniques as part of a drug use testing program or in a forensic investigation. Recreational use of cannabis is now legal in many parts of North America and it has increased the demand for new platforms for monitoring THC for both personal and law enforcement applications. Breath sampling as a noninvasive method is has shown promising results to detect THC. Scientists and industry researchers are commercializing various types of breath analyzers to monitor THC in breath \\\\\\\\\\\\\\\\\\\\\[40\\\\\\\\\\\\\\\\\\\\\]. Female cannabis plants contain at least cannabinoids, \\\\\\\\\\\\\\\\\\\\\[44\\\\\\\\\\\\\\\\\\\\\] including cannabidiol CBD , thought to be the major anticonvulsant that helps people with multiple sclerosis ; \\\\\\\\\\\\\\\\\\\\\[45\\\\\\\\\\\\\\\\\\\\\] and cannabichromene CBC , an anti-inflammatory which may contribute to the pain-killing effect of cannabis. As of October when recreational use of cannabis was legalized in Canada, some dietary supplements and 19 veterinary health products containing not more than 10 parts per million of THC extract were approved with general health claims for treating minor conditions. The status of THC as an illegal drug in most countries imposes restrictions on research material supply and funding, such as in the United States where the National Institute on Drug Abuse and Drug Enforcement Administration regulated sources of cannabis for researchers until August when licenses were provided to growers for supplies of medical marijuana. In April , the American Academy of Neurology found evidence supporting the effectiveness of the cannabis extracts in treating certain symptoms of multiple sclerosis and pain, but there was insufficient evidence to determine effectiveness for treating several other neurological diseases. From Wikipedia, the free encyclopedia. For other uses, see THC disambiguation. US : C Risk not ruled out. IUPAC name. Interactive image. Further information: Dronabinol. Not to be confused with Droperidol. See also: Effects of cannabis , Long-term effects of cannabis , and Cannabis in pregnancy. For a review of the mechanisms behind endocannabinoid synaptic transmission, see Endocannabinoid system. Main article: Cannabis drug testing. Further information: Medical cannabis. Arts Culture. Edibles Smoking Tea. Drug culture Illegal drug trade Psychedelia. Cannabis portal Chemistry portal. Archived from the original PDF on Retrieved Clin Pharmacokinet. In Sean C. Sweetman ed. Pharmaceutical Press. National Center for Biotechnology Information. Retrieved 12 January April Journal of the American Chemical Society. August Isomerization to Tetrahydrocannabinols'. Oxford: Biology. Journal of the International Hemp Association. Economic Botany. Photochemistry and Photobiology. Chemical Communications. Retrieved 14 January US Food and Drug Administration. September UK Electronic Medicines Compendium. March Government of Canada. Retrieved 19 October Archived from the original on 8 November Retrieved 11 June International Journal of Obesity. British Journal of Pharmacology. Appl Environ Microbiol. Br J Psychiatry. Because they are extremely lipid soluble, cannabinoids accumulate in fatty tissues, reaching peak concentrations in 4—5 days. They are then slowly released back into other body compartments, including the brain. Within the brain, THC and other cannabinoids are differentially distributed. High concentrations are reached in neocortical, limbic, sensory and motor areas. Chem Biodivers. THC is highly lipophilic and initially taken up by tissues that are highly perfused, such as the lung, heart, brain, and liver. Drug Testing and Analysis. Life Science. Handbook of Experimental Pharmacology. Clark Bibcode : Sci FEBS Letters. Journal of Experimental Botany. J Pharm Pharmacol. Clinical Chemistry. Journal of Analytical Toxicology. Disposition of Toxic Drugs and Chemicals in Man 9th ed. Journal of Breath Research. February Archived from the original on Chemical Heritage Newsmagazine. Archived from the original on 19 June World Health Organization. Journal of Natural Products. In Kinghorn, A. Progress in the Chemistry of Organic Natural Products. Springer International Publishing. Multidisciplinary Association for Psychoactive Substances. F; Wolff, R. V; Keurentjes, J. Krishnan S ed. WIN 55, Cannabis plant. Outline of cannabis Recreational and medical applications Industrial applications. Autoflowering cannabis Cannabis indica ruderalis sativa Difference between C. Medical cannabis Cannabis product testing History Medical cannabis research Timeline Religious and spiritual use Chalice. Adult lifetime use by country Annual use by country. Cannabis political parties List of British politicians who have acknowledged cannabis use List of American politicians who have acknowledged cannabis use. Ker v. California Leary v. United States Gonzales v. Raich Kyllo v. Cannabis portal Category. Medical and recreational uses. Recreational drug use. Calea zacatechichi Silene capensis. Coffee break Coffeehouse Latte art Tea house. Abuse Date rape drug Impaired driving Drug harmfulness Effects of cannabis Addiction Dependence Prevention Opioid replacement therapy Rehabilitation Responsible use Drug-related crime Fetal alcohol spectrum disorder Long-term effects of cannabis Neurotoxicity Overdose Passive smoking of tobacco or other substances. Alcohol legality Alcohol consumption Anabolic steroid legality Cannabis legality Annual use Lifetime use Cigarette consumption Cocaine legality Cocaine use Methamphetamine legality Opiates use Psilocybin mushrooms legality Salvia legality. See also: Recreational drug use. Diphenidine Ephenidine Fluorolintane Methoxphenidine. Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan. Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D 2 agonists, such as dopamine reuptake inhibitors cocaine , methylphenidate , releasing agents amphetamine , methamphetamine , and precursors levodopa. Glaucine Isoaminile Noscapine Pukateine. Antiemetics A Dronabinol Nabilone Tetrahydrocannabinol cannabis. Atropine Diphenhydramine Hydroxyzine very mild Hyoscyamine Scopolamine. Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol. Appetite stimulants A Ancient anaesthesia. Acetylcholine metabolism and transport modulators. Inhibitors: Hemicholinium-3 hemicholine Triethylcholine Enhancers: Coluracetam. Inhibitors: Vesamicol. Cannabinoid receptor modulators. Agonists: Revosimeline. Glycine receptor modulators. See here instead. Opioid receptor modulators. TRP channel modulators. Dehydroligustilide celery Nicotine tobacco Ruthenium red. Triptolide Tripterygium wilfordii. Ruthenium red. Xenobiotic-sensing receptor modulators. Hidden categories: CS1 errors: missing periodical CS1 maint: archived copy as title Wikipedia articles needing page number citations from January CS1 maint: multiple names: authors list Drugs with non-standard legal status Articles with changed EBI identifier ECHA InfoCard ID from Wikidata Infobox drug articles with non-default infobox title Articles without KEGG source Drugboxes which contain changes to verified fields Drugboxes which contain changes to watched fields All articles lacking reliable references Articles lacking reliable references from March Namespaces Article Talk. Views Read Edit View history. In other projects Wikimedia Commons. By using this site, you agree to the Terms of Use and Privacy Policy. Mostly hepatic by CYP2C \\\\\\\\\\\\\\\\\\\\\[3\\\\\\\\\\\\\\\\\\\\\]. Consumption Edibles Smoking Tea. Related Drug culture Illegal drug trade Psychedelia. Cannabis portal Medicine portal Agriculture portal. Activators Triptolide Tripterygium wilfordii.
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