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|Systematic (IUPAC) name|
|Mol. mass||149.19 g/mol|
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Cathinone // (also known as benzoylethanamine, or β-keto-amphetamine also known as hagigat (Hebrew: חגיגת "celebration") in Israel,) is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. 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.
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 is structurally related to methcathinone, in much the same way as amphetamine is related to methamphetamine. Cathinone differs from amphetamine by possessing a ketone oxygen atom (C=O) on the β (beta) position of the side chain. The corresponding alcohol compound 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.
Cathinone can be extracted from Catha edulis, or synthesized from α-bromopropiophenone (which is easily made from propiophenone). 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.
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- Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B (2008). "Illicit cathinone ("Hagigat") poisoning". Clin Toxicol (Phila) 46 (3): 206–10. doi:10.1080/15563650701517574. PMID 17852166.
- "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. United Nations. 2003. Archived from the original on 2012-08-31.
- "Synthetic Street Drug Camouflaged as Bath Salts Has Dangerous, Bizarre Effects". PBS NewsHour. 20 September 2012. Retrieved 7 December 2013.
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