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Cathinone (; also known as β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. 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 phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.
A study was conducted in 1994 to test the effects of cathinone. Six volunteers who had never chewed khat were given an active khat sample and a cathinone-free placebo sample. The researchers analyzed the participants' moods, activity levels and blood pressure before and after consuming the khat or placebo. This analysis showed that cathinone produced amphetamine-like effects, leading the researchers to confirm that cathinone, not cathine, is the active ingredient in khat leaves.
In order to produce its desired effects, khat leaves should be chewed fresh. The fresh leaves have a higher concentration of cathinone. Waiting too long after cultivation to chew the leaf will allow the cathinone to break down into its less potent form, cathine. Because of the need for quick chewing, it is a habit that has historically been prevalent only where the plant grows. However, in the recent years with improvements in road and air transport, khat chewing has spread to all corners of the world.
The cultivation of khat in Yemen is a highly profitable industry for farmers. Khat plants will grow differently depending on the climate they are grown in and each one will produce different amounts of cathinone. It generally grows best in coastal, hot climates. In Yemen, the khat plant is named after the region in which it is grown. The Nehmi khat plant has the highest known concentration of cathinone, 342.5 mg/100 g.
The sale of khat is legal in some jurisdictions, but illegal in others (see Khat (Regulation)). Substituted cathinones were also often used as the key ingredient of recreational drug mixes commonly known as "bath salts" in the United States.
The table below shows the legality of khat and cathinone in various countries:
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(2025). 9783319524429, Springer. ISBN 9783319524429 | ||||
| Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The bioassay were done in rat brain and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: | ||||
Cathinone has been found to stimulate the release of dopamine and inhibit the reuptake of epinephrine, norepinephrine and serotonin in the central nervous system (CNS). These neurotransmitters are all considered and share the general structure of an aromatic ring and an amine group attached by a two-carbon separator. Because cathinone is a hydrophobic molecule, it can easily cross cell membranes and other barriers, including the blood–brain barrier. This property allows it to interact with the monoamine transporters in the synaptic cleft between neurons. Cathinone induces the release of dopamine from brain striatal preparations that are prelabelled either with dopamine or its precursors. It is more specifically a norepinephrine–dopamine releasing agent (NDRA) similarly to amphetamine.
The metabolites of cathinone, cathine and norephedrine, also possess CNS stimulation, but create much weaker effects. The effects of cathinone on the body can be countered by a preceding administration of a dopamine receptor antagonist. The antagonist prevents synaptic dopamine released by cathinone from exerting its effect by binding to dopamine receptors.
Cathinone can also affect cholinergic concentrations in the gut and airways by blocking prejunctional adrenergic receptors (α2 adrenergic) and activating 5-HT7 receptors, thereby inhibiting smooth muscle contraction. It can also induce dry mouth, blurred vision and increased blood pressure and heart rate.
Cathinone is a weak agonist of the mouse, rat, and human trace amine-associated receptor 1 (TAAR1). In contrast to cathinone however, most other cathinones are not human TAAR1 agonists. TAAR1 activation may auto-inhibit and constrain the monoaminergic effects of monoamine releasing agents possessing TAAR1 agonism. (2025). 9783319489254, Springer International Publishing. ISBN 9783319489254
Khat chewing and the effects of cathinone on the body differ from person to person, but there is a general pattern of behavior that emerges after ingesting fresh cathinone:
There are other effects not related to the CNS. The chewer can develop constipation and heartburn after a khat session. Long-term effects of cathinone can include gum disease or oral cancer, cardiovascular disease and depression. The withdrawal symptoms of cathinone include hot flashes, lethargy and a great urge to use the drug for at least the first two days.
Aside from the beta- and non-beta-oxidative pathways, the biosynthesis of cathinone can proceed through a CoA-dependent pathway. The CoA-dependent pathway is actually a mix between the two main pathways as it starts like the beta-oxidative pathway and then when it loses CoA, it finishes the synthesis in the non-beta-oxidative pathway. In this pathway, the trans-cinnamic acid produced from L-phenylalanine is ligated to a Coenzyme A (CoA), just like the beginning of the beta-oxidative pathway. It then undergoes hydration at the double bond. This product then loses the CoA to produce benzaldehyde, an intermediate of the non-beta-oxidative pathway. Benzaldehyde is converted into benzoic acid and proceeds through the rest of the synthesis.
The structure of cathinone is very similar to that of other molecules. By reducing the ketone, it becomes cathine if it retains its stereochemistry, or norephedrine if its stereochemistry is inverted. Cathine is a less potent version of cathinone and cathinone's spontaneous reduction is the reason that older khat plants are not as stimulating as younger ones. Cathinone and amphetamine are closely related in that amphetamine is only lacking the ketone C=O group. 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. Advancements in synthesizing cyclic cathinones based on α-tetralone have employed chiral HPLC-CD techniques to determine the absolute configuration of enantiomers, an approach that may contribute to the development of pharmaceutical analogs with antidepressant potential. The corresponding substance 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.
There are many cathinone derivatives that include the addition of an R group to the amino end of the molecule. Some of these derivatives have medical uses as well. Bupropion is one of the most commonly prescribed antidepressants and its structure is Cathinone with a tertiary butyl group attached to the nitrogen and chlorine attached to the benzene ring meta- to the main carbon chain.
Other cathinone derivatives are strong psychoactive drugs. One such drug is methylone, a drug structurally similar to MDMA.
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