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Cathinone

Cathinone
Cathinone2DACS.svg
Cathinone-3d-CPK.png
Clinical data
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Biological half-life 0.7–2.3 h
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.163.927
Chemical and physical data
Formula C9H11NO
Molar mass 149.19 g/mol
3D model (Jmol)
 NYesY (what is this?)  

Cathinone /ˈkæθnn/ (also known as benzoylethanamine, or β-keto-amphetamine) 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 among others.

Khat has been cultivated in the Horn of Africa and Arabian Peninsula region of the world for thousands of years. It is most commonly chewed for the euphoric effect it produces. The active ingredient was first proposed in 1930, when cathine was identified as a predominant alkaloid in the plant. Cathine was thought to be the main active ingredient in khat until the 1960s, when it was found that the amount of cathine in the khat leaves is insufficient to produce the effects observed. In 1975, the United Nations Narcotic Laboratory analyzed khat leaves from Yemen, Kenya and Madagascar and found the presence of a different alkaloid, cathinone. Cathinone is a similar molecule to cathine, but is much more abundant in younger plants. This finding caused scientists to speculate about whether cathinone was the true active ingredient in khat.


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