|This article needs additional citations for verification. (December 2007)|
|Systematic (IUPAC) name|
|Legal status||Prohibited (S9) (AU) Schedule III (CA) Class C (UK) Schedule I (US)|
|Mol. mass||149.19 g/mol|
|(what is this?)|
Cathinone //, benzoylethanamine, or β-ketone-amphetamine also known as hagigat (Hebrew: חגיגת) in Israel, is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors. 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 amphetamines that share this structure include the antidepressant bupropion and the stimulant methcathinone, 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.
- Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.. Toennes SW, et al. (2003 Jul). Retrieved on 2014-01-30.
- Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B (March 2008). "Illicit cathinone ("Hagigat") poisoning". Clin Toxicol (Phila) 46 (3): 206–10. doi:10.1080/15563650701517574. PMID 17852166.
- Kalix P (1981). "Cathinone, an alkaloid from khat leaves with an amphetamine-like releasing effect". Psychopharmacology (Berl.) 74 (3): 269–70. doi:10.1007/BF00427108. PMID 6791236.
- "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.
- Shulgin, Alexander (7 December 2005). "4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin". Ask Dr. Shulgin Online. Retrieved 10 September 2013.
- Erowid Cathinone Vault
- Cathinone Popularity Soars in Israel
- Photos of cathinone before it is extracted from khat