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It is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone , MDPV , mephedrone and the antidepressant bupropion among others. Khat has been cultivated in the Horn of Africa and Arabian Peninsula region of the world for thousands of years. It is most commonly chewed for the euphoric effect it produces. The active ingredient was first proposed in , when cathine was identified as a predominant alkaloid in the plant. In , the United Nations Narcotic Laboratory analyzed khat leaves from Yemen , Kenya and Madagascar and found the presence of a different alkaloid, cathinone. This finding caused scientists to speculate about whether cathinone was the true active ingredient in khat. A study was conducted in to test the effects of cathinone. Six volunteers who had never chewed khat were given an active khat sample and a cathinone-free placebo sample. This analysis showed that cathinone produced amphetamine-like symptoms, leading the researchers to confirm that cathinone, not cathine, is the active ingredient in khat leaves. Over 20 million people in the Arabian Peninsula and East Africa chew khat leaves daily. It is an important piece of the culture and economy in this region, especially in Ethiopia where khat is said to have originated , Kenya, Djibouti , and Yemen. Men usually chew it during parties or other social gatherings while smoking cigarettes and drinking tea. Farmers and other workers also use khat in the afternoon to reduce fatigue and hunger as the day goes on. It functions like the caffeine in a strong cup of coffee as an anti-fatigue drug. Students and drivers have been known to use it to stay alert for longer periods of time. In order to produce its desired effects, khat leaves should be chewed fresh. The fresh leaves have a higher concentration of cathinone. Waiting too long after cultivation to chew the leaf will allow the cathinone to break down into its less potent form, cathine. Because of the need for quick chewing, it is a habit that has historically been prevalent only where the plant grows. However, in the recent years with improvements in road and air transport, khat chewing has spread to all corners of the world. The cultivation of khat in Yemen is a highly profitable industry for farmers. Khat plants will grow differently depending on the climate they are grown in and each one will produce different amounts of cathinone. In Yemen, the khat plant is named after the region in which it is grown. The Nehmi khat plant has the highest known concentration of cathinone, The sale of khat is legal in some jurisdictions, but illegal in others see Khat Regulation. Substituted cathinones were also often used as the key ingredient of recreational drug mixes commonly known as ' bath salts ' in the United States. Cathinone has been found to stimulate the release of dopamine and inhibit the reuptake of epinephrine , norepinephrine and serotonin in the central nervous system CNS. These neurotransmitters are all considered monoamines and share the general structure of an aromatic ring and an amine group attached by a two-carbon separator. Cathinone induces the release of dopamine from brain striatal preparations that are prelabelled either with dopamine or its precursors. The metabolites of cathinone, cathine and norephedrine also possess CNS stimulation, but create much weaker effects. Cathinone can also affect the peripheral nervous system PNS by blocking adrenergic receptors and inhibiting smooth muscle contraction. Khat leaves are removed from the plant stalk and are kept in a ball in the cheek and chewed. Chewing releases juices from the leaves, which include the alkaloid cathinone. The absorption of cathinone has two phases: The mean residence time is 5. Cathinone has been shown to selectively metabolize into R,S- - -norephedrine and cathine. The reduction of the ketone group in cathinone will produce cathine. This reduction is catalyzed by enzymes in the liver. The spontaneous breakdown of cathinone is the reason it must be chewed fresh after cultivation. The first documentation of the khat plant being used in medicine was in a book published by an Arabian physician in the 10th century. Chronic khat chewing can also create drug dependence, as shown by animal studies. Khat chewing and the effects of cathinone on the body differ from person to person, but there is a general pattern of behavior that emerges after ingesting fresh cathinone: There are other effects not related to the CNS. The chewer can develop constipation and heartburn after a khat session. Long-term effects of cathinone can include gum disease or oral cancer , cardiovascular disease and depression. The synthesis of cathinone in khat begins with L-phenylalanine and the first step is carried out by L-phenylalanine ammonia lyase PAL , which cleaves off an ammonia group and creates a carbon-carbon double bond, forming cinnamic acid. The beta-oxidative pathway produces benzoyl-CoA while the non-beta-oxidative pathway produces benzoic acid. S -Cathinone can then undergo a reduction reaction to produce the less potent but structurally similar cathine or norephedrine, which are also found in the plant. Aside from the beta- and non-beta-oxidative pathways, the biosynthesis of cathinone can proceed through a CoA-dependent pathway. The CoA-dependent pathway is actually a mix between the two main pathways as it starts like the beta-oxidative pathway and then when it loses CoA, it finishes the synthesis in the non-beta-oxidative pathway. In this pathway, the trans-cinnamic acid produced from L-phenylalanine is ligated to a Coenzyme A CoA , just like the beginning of the beta-oxidative pathway. This product then loses the CoA to produce benzaldehyde , an intermediate of the non-beta-oxidative pathway. Benzaldehyde is converted into benzoic acid and proceeds through the rest of the synthesis. Cathinone can be synthetically produced from propiophenone through a Friedel-Crafts Acylation of propionic acid and benzene. A different synthetic strategy must be employed to produce enantiomerically pure S -cathinone. This synthetic route starts out with the N-acetylation of the optically active amino acid , S-alanine. At the same time, a Friedel-Crafts acylation is preformed on benzene with aluminum chloride catalyst. Finally, the acetyl protecting group is removed by heating with hydrochloric acid to form enantiomerically pure S- - -cathinone. Because cathinone is both a primary amine and a ketone , it is very likely to dimerize , especially as a free base isolated from plant matter. The structure of cathinone is very similar to that of other molecules. By reducing the ketone, it becomes cathine if it retains its stereochemistry, or norephedrine if its stereochemistry is inverted. The corresponding alcohol, cathine , is a less powerful stimulant. The biophysiological conversion from cathinone to cathine is to blame for the depotentiation of khat leaves over time. Fresh leaves have a greater ratio of cathinone to cathine than dried ones, therefore having more psychoactive effects. There are many cathinone derivatives that include the addition of an R group to the amino end of the molecule. Some of these derivatives have medical uses as well. Bupropion is one of the most commonly prescribed antidepressants and its structure is Cathinone with a tertiary butyl group attached to the nitrogen and chlorine attached to the benzene ring meta- chemistry to the main carbon chain. Other cathinone derivatives are strong psychoactive drugs. One such drug is methylone , a drug structurally similar to MDMA. From Wikipedia, the free encyclopedia. This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. December Learn how and when to remove this template message. Anlage I Authorized scientific use only UK: Two mechanism of synthesizing Cathinone. Br J Clin Pharmacol. East African Medical Journal. Clinical Pharmacology and Therapeutics. Archived from the original on 12 October Retrieved 20 March International Narcotics Control Board. Archived from the original PDF on Archived from the original on 7 December Retrieved 7 December What you need to know about flakka, the latest drug causing erratic behaviour - National Globalnews. Retrieved 3 August Archived PDF from the original on History, Synthesis, and Human Applications'. Archived from the original on 4 July Retrieved 8 March Archived from the original on 23 April Retrieved 10 March Genetics and Molecular Biology. Archived from the original on 7 September Retrieved 10 September Archived from the original on 17 March Adapromine Amantadine Bromantane Memantine Rimantadine. Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide. SoRI Adrenergic release blockers: Retrieved from ' https: Drugs not assigned an ATC code Cathinones Amphetamine alkaloids Drugs acting on the cardiovascular system Euphoriants Norepinephrine-dopamine releasing agents Stimulants Phenyl compounds. Views Read Edit View history. In other projects Wikimedia Commons. This page was last edited on 3 August , at By using this site, you agree to the Terms of Use and Privacy Policy. Legal — The khat plant leaves are allowed to be chewed and beverages containing khat are legal, but it is illegal to sell pills based on cathinone extracts. Khat is regulated under the Australian Customs Service and a special permit is needed to import it for personal use. The khat plant itself is allowed to be sold and chewed, but it is illegal to sell or make beverages containing khat. Illegal under List I - 'Plants and substances with a high risk to the public health due to their harmful effect of misuse, prohibited for use in human and veterinary medicine' \\\\\\\\\\\\\\\\\[11\\\\\\\\\\\\\\\\\].

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