Cathinone

Cathinone, or Benzoylethanamine, 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. 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. Circa 1993, the DEA added cathinone to the Controlled Substances Act's Schedule I.

The sale of khat is legal in Israel (although synthetic cathinone is not), and also in Oman, in Yemen, in the United Kingdom and in the Horn of Africa.

Chemistry


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).

Toxic effects
Excessive cathinone usage can cause loss of appetite, anxiety, irritability, insomnia, hallucinations and panic attacks. Chronic abusers are at risk of developing personality disorders and of sustaining myocardial infarction. Please note that the drug referred to in this article was actually the closely-related mephedrone, a cathinone derivative which does not occur in nature. Mephedrone has more power as a releasing agent of serotonin than of cathinone or methcathinone, hence its use in party pills as a "legal" replacement for MDMA Persons driving under the influence of the drug have had their serum or urine tested for the presence of cathinone and norephedrine, a major metabolite.