Cathinone
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220767581
2008-06-21T13:59:56Z
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{{Refimprove|date=December 2007}}
{{Drugbox|
|IUPAC_name = ''(S)''-2-amino-1-phenyl-1-propanone
| image=Cathinone structure.svg
| image2=Cathinone-3d-CPK.png
| width = 175px
| CAS_number=71031-15-7
| ATC_prefix=
| ATC_suffix=
| ATC_supplemental=
| PubChem=
| DrugBank=
| C=9 | H=11 | N=1 | O=1
| molecular_weight = 149.19 g/mol
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion =
| pregnancy_category =
| legal_US = Schedule I
| legal_CA = Schedule III
| legal_UK = Class A
| routes_of_administration=
}}
'''Cathinone''' (''β''-[[ketone|keto]][[amphetamine]]) is a [[monoamine]] [[alkaloid]] found in the [[shrub]] ''[[Catha edulis]]'' ([[Khat]]) and is chemically similar to [[ephedrine]], [[cathine]] and other [[amphetamines]]. Amphetamine induces the release of [[dopamine]] from striatal preparations that are prelabelled either with dopamine or its precursors, and it has been shown that cathinone also does this.<ref>{{cite journal |last=Kalix |first=Peter |year=1981 |month=February |title=Cathinone, an alkaloid from khat leaves with an amphetamine-like releasing effect |journal=Psychopharmacology |volume=74 |issue=3 |pages=269–70 |url=http://www.springerlink.com/content/n7v28h68627245j0/?p=95742099c2304cc9b83799274e8bbcdc&pi=2 |accessdate= 2008-02-11 |doi=10.1007/BF00427108}}</ref>. 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]].<ref>[http://www.incb.org/pdf/e/list/green.pdf List of psychotropic substances under international control]</ref> Circa 1993, the [[Drug Enforcement Administration|DEA]] added cathinone to the [[Controlled Substances Act]]'s Schedule I in order to fulfill the requirements of international law.
The sale of [[khat]] is legal in [[Israel]] (although synthetic cathinone is not), and also in [[Oman]], in [[Yemen]], and in the [[Horn of Africa]].
==Chemistry==
[[Image:Cathinone-3d-sticks.png|left|200px|thumb|The molecular structure of cathinone.]]
Cathinone is structurally related to [[methcathinone]], much like how [[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.<!--Cathinone is easily converted into an [[alcohol]] (C-OH)-- under which conditions? citation needed!--> 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''-[[bromine|bromo]][[propiophenone]] (which is easily made from [[propiophenone]]).
==References==
* Erowid Cathinone Vault [http://www.erowid.org/chemicals/cathinone/]
<references/>
==External links==
*[http://www.guardian.co.uk/israel/Story/0,2763,1296958,00.html Cathinone Popularity Soars in Israel]
{{Amphetamines}}
[[Category:Amphetamine alkaloids]]
[[Category:Amines]]
[[Category:Amphetamines]]
[[Category:Aromatic compounds]]
[[Category:Ketones]]
[[Category:Stimulants]]
[[fr:Cathinone]]
[[nl:Cathinon]]
[[pl:Katynon]]
[[sv:Katinon]]