Cathinone, a Natural Amphetamine

Abstract

Cathinone is an alkaloid that has been discovered some fifteen years ago in the leaves of the khat bush. This plant grows in East Africa and in southern Arabia, and the inhabitants of these regions frequently chew khat because of its stimulating properties. Cathinone, which is S(-)-alpha-aminopropiophenone, was soon found to have a pharmacological profile closely resembling that of amphetamine; indeed, in a wide variety of in vitro and in vivo experiments it was demonstrated that cathinone shares the action of amphetamine on CNS as well as its sympathomimetic effects; thus, for example, drug-conditioned animals will not distinguish between cathinone and amphetamine. These various observations were confirmed by a clinical experiment showing that cathinone also in humans produces amphetamine-like objective and subjective effects. Finally, it was demonstrated that cathinone operates through the same mechanism as amphetamine, i.e. it acts by releasing catecholamines from presynaptic storage sites. Thus, much experimental evidence indicates that cathinone is the main psychoactive constituent of the khat leaf and that, in fact, this alkaloid is a natural amphetamine.

Khat (Catha edulis)-induced apoptosis is inhibited by antagonists of caspase-1 and -8 in human leukaemia cells

“…These phenylpropylamines, structurally related to amphetamine and ephedrine, are considered the major bioactive compounds in khat extract (Kalix, 1992). To our knowledge, these khat-specific phenylpropylamines have not previously been reported to be associated with induction of apoptosis.…”

“…Cathinone is a major alkaloid component in fresh Catha leaves, but is relatively unstable and is rapidly metabolised into norpseudoephedrine (cathine) and norephedrine. Other alkaloid compounds such as the phenylpentenylamines and cathedulines could also contribute to pharmacological effects of khat (Kalix, 1992;Al-Motarreb et al, 2002). Most of their pharmacological effects are suggested as being mediated by release of biogenic amines through preferential binding to the norepinephrine receptor/transporter, but also partly through binding to dopamine and 5-hydroxytryptamine receptors (Rothman et al, 2003).…”

Mephedrone-Related Fatalities in the United Kingdom: Contextual, Clinical and Practical Issues

“…Cathinone is a natural amphetamine-like alkaloid found in the fresh leaves and stems of the African shrub Khat (Catha edulis) (Kalix, 1992). The systematic name of mephedrone is 2-(methylamino)-1-(p-tolyl)propan-1-one(2S)-2-(methylamino)-1-(4-methylphenyl)propan-1-one, in accordance with the International Union of Pure and Applied Chemistry.…”

A comprehensive computational analysis of cathinone and its metabolites using quantum mechanical approaches and docking studies

“…Along with cathinone, other less potent stimulant substances are also present in khat leaves, namely norephedrine and norpseudoephedrine (cathinone) [5]. Taking into account the structural and pharmacological properties of amphetamine and cathinone, it can be concluded that they should act similarly by inducing dopamine releases from central dopaminergic nerve terminals, thus increasing the activity of dopaminergic pathways [6,7].…”