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Cathinone

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Cathinone
Systematic (IUPAC) name
(S)-2-amino-1-phenyl-1-propanone
Identifiers
CAS number	71031-15-7
ATC code	?
PubChem	?
Chemical data
Formula	C₉H₁₁N O
Mol. mass	149.19 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule III(CA) Class A(UK) Schedule I(US)
Routes	?

Indicated for:

Recreational uses:

Yes, used by chewing the leaves of the Khat plant to produce stimulant effects.

Unethical uses:

Other uses:

Contraindications:

Side effects:

Severe:

Atypical sensations:

Cardiovascular:

Ear, nose, and throat:

May cause temporary tinnitis (ringing in the ears)

Endocrinal:

Eye:

Gastrointestinal:

Hematological:

Musculoskeletal:

Neurological:

Psychological:

Respiratory:

Skin:

Urogenital and reproductive:

Miscellaneous:

Cathinone (β-keto amphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). Closely related to ephedrine, cathine and other amphetamines, it is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that its structure is a ketone. Other amphetamines to share this structure include the antidepressant bupropion and the stimulant methcathinone, among others.

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Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances.^[1] Circa 1993, the DEA added cathinone to the Controlled Substances Act's Schedule I in order to fulfill the requirements of international law.

The commerce of Khat is legal in Israel (although synthesized Cathinone is not), in Oman, in Yemen, and in the Horn of Africa.

Chemistry

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 holding a more psychoactive potential.

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

References

^ List of psychotropic substances under international control

v • d • e Amphetamines (N06BA)
Amphetamine/dl-Amphetamine, Dextroamphetamine, Dextromethamphetamine, Levomethamphetamine, 4-FMP, 4-MTA, Benzphetamine, Ethylamphetamine, Propylamphetamine, MDMA, MDA, MDEA, N-methyl-β-hydroxyamphetamine, Parahydroxyamphetamine, Paramethoxyamphetamine, Paramethoxymethamphetamine, Paramethoxyethylamphetamine, Xylopropamine

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