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Cathinone
Systematic (IUPAC) name
(S)-2-amino-1-phenyl-1-propanone
Clinical data
Pregnancy cat.  ?
Legal status Schedule III (CA) Class C (UK) Schedule I (US)
Identifiers
CAS number 71031-15-7 YesY
ATC code None
PubChem CID 62258
DrugBank DB01560
ChemSpider 56062 YesY
UNII 540EI4406J YesY
KEGG C08301 YesY
ChEBI CHEBI:4110 YesY
Chemical data
Formula C9H11NO 
Mol. mass 149.19 g/mol
 YesY (what is this?)  (verify)

Cathinone[pronunciation?], or benzoylethanamine (marketed as hagigat in Israel[1]), is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors.[2] 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.

Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances.[3] Circa 1993, the DEA added cathinone to the Controlled Substances Act's Schedule I.

The sale of khat is legal in some jurisdictions, but illegal in others — see Khat (Regulation). Synthetic cathinone is also often used as the key ingredient of recreational drug mixes commonly known as 'bath salts' in the United States.[4]

Contents

Chemistry [edit]

The molecular structure of cathinone.

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).

See also [edit]

References [edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ International Narcotics Control Board (2003). "List of psychotropic substances under international control" (pdf). United Nations. 
  4. ^ http://www.pbs.org/newshour/bb/science/july-dec12/bathsalts_09-20.html

External links [edit]


Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Cathinone — Please support Wikipedia.
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25 news items

UPI.com

UPI.com
Tue, 21 May 2013 15:10:18 -0700

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 on the beta position of the side chain. Because its chemical ...
 
SILive.com
Tue, 21 May 2013 04:13:10 -0700

Khat refers to cathinone, a Schedule 1 controlled substance in the United States. It is most typically chewed to experience euphoria and stimulation, though federal authorities say side effects can range from anorexia to heart disease and hypertension, ...
 
Phys.Org (press release)
Fri, 17 May 2013 13:56:19 -0700

Bath salts refers to an emerging family of drugs containing one or more synthetic chemicals related to cathinone, an amphetamine-like stimulant found naturally in the Khat plant. She looked at three possible effects: mortality, feeding patterns and ...
 
ABC Online
Fri, 10 May 2013 14:41:56 -0700

... of cocaine or amphetamines. This never happens in South America as metabolically once one is off the cocaine high one can easily fall asleep. It is the same with the world's second best stimulant Khat.... active ingedient cathinone. Reply Alert ...

PR Web (press release)

PR Web (press release)
Thu, 09 May 2013 00:22:24 -0700

Research indicates that use of the mind-altering drug Khat causes serious side effects to brain chemistry and leaves a person craving its addictive taste. Pronounced “cot,” Khat contains cathinone, a controlled substance with no recognized therapeutic use.
 
Lake County News Sun
Thu, 02 May 2013 14:13:20 -0700

Lake County Metropolitan Enforcement Group (MEG) received a tip that Mohamed would be at Lake Forest Pack and Ship, located at 736 N. Western Ave., Lake Forest, to receive three boxes of cathinone, Lake County State's Attorney spokeswoman Cynthia ...

The Guardian

The Guardian
Fri, 26 Apr 2013 14:01:48 -0700

It was a cathinone: a drug in the amphetamine family that occupied a sweet spot between the bonhomie of ecstasy and the brittle buzz of cocaine. Most of all, it was legal. In recession-hit Britain in 2009, when cocaine purity had plummeted and ecstasy ...
 
Psychiatric Times
Tue, 30 Apr 2013 07:24:31 -0700

Speaking of these drugs as a homogenous group (and the only time this article doesn't do this, the information provided is factually wrong or misleading) is of dubious value, as anyone who has ever prescribed bupropion (another substituted cathinone ...
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