Cathinone

Drugbox
IUPAC_name = "(S)"-2-amino-1-phenyl-1-propanone

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CAS_number=71031-15-7
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C=9 | H=11 | N=1 | O=1
molecular_weight = 149.19 g/mol
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legal_US = Schedule I
legal_CA = Schedule III
legal_UK = Class A
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Cathinone ("β"-ketoamphetamine) 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. [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] . 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. [ [http://www.incb.org/pdf/e/list/green.pdf List of psychotropic substances under international control] ] Circa 1993, the 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

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. 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).

References

* Erowid Cathinone Vault [http://www.erowid.org/chemicals/cathinone/]

External links

* [http://www.guardian.co.uk/israel/Story/0,2763,1296958,00.html Cathinone Popularity Soars in Israel]