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Cathinone
Systematic (IUPAC) name
(S)-2-amino-1-phenyl-1-propanone
Identifiers
CAS number 71031-15-7
ATC code none
PubChem 62258
Chemical data
Formula C 9H11NO 
Mol. mass 149.19 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule III (CA) Class C (UK) Schedule I (US)
Routes  ?

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.[1] 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.[2] 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 United Kingdom and in the Horn of Africa.

Chemistry

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. 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

External links








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