Cathinone (/ˈkæθɪnoʊn/; 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.

Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.

Khat has been cultivated in the Horn of Africa and Arabian Peninsula region of the world for thousands of years.

In 1975, the United Nations Narcotic Laboratory analyzed khat leaves from Yemen, Kenya and Madagascar and found evidence of a different alkaloid, cathinone.

[5] The researchers analyzed the participants' moods, activity levels and blood pressure before and after consuming the khat or placebo.

[5] Over 20 million people in the Arabian Peninsula and East Africa chew khat leaves daily.

It is an important piece of the culture and economy in this region, especially in Ethiopia (where khat is said to have originated), Kenya, Djibouti, Somalia and Yemen.

Waiting too long after cultivation to chew the leaf will allow the cathinone to break down into its less potent form, cathine.

However, in the recent years with improvements in road and air transport, khat chewing has spread to all corners of the world.

Substituted cathinones were also often used as the key ingredient of recreational drug mixes commonly known as "bath salts" in the United States.

These neurotransmitters are all considered monoamines and share the general structure of an aromatic ring and an amine group attached by a two-carbon separator.

[30][31] The metabolites of cathinone, cathine and norephedrine, also possess CNS stimulation, but create much weaker effects.

[37][36] TAAR1 activation may auto-inhibit and constrain the monoaminergic effects of monoamine releasing agents possessing TAAR1 agonism.

[5] At approximately 2.3 hours after chewing khat leaves, the maximum concentration of cathinone in blood plasma is reached.

[7] The withdrawal symptoms of cathinone include hot flashes, lethargy and a great urge to use the drug for at least the first two days.

(S)-Cathinone can then undergo a reduction reaction to produce the less potent but structurally similar cathine or norephedrine, which are also found in the plant.

Finally, the acetyl protecting group is removed by heating with hydrochloric acid to form enantiomerically pure S-(-)-cathinone.

[32] Cathinone can be extracted from Catha edulis (khat), or synthesized from α-bromopropiophenone (which is easily made from propiophenone).

Because cathinone is both a primary amine and a ketone, it is very prone to dimerization, especially as a free base isolated from plant matter.

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.