Structure via PubChem · Public domain (PubChem)
(−)-cathinone
Sign in to saveAlso known as D-Cathinone, β-ketoamphetamine, Cathinone, Norephedrone
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.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 447622611
- Drug.IUPAC_name
- (S)-2-Amino-1-phenylpropan-1-one
- Drug.image
- Cathinone.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Cathinone molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.legal_AU
- S9
- Drug.legal_BR
- F2
- Drug.legal_CA
- Schedule III
- Drug.legal_DE
- Anlage I
- Drug.legal_UK
- Class c
- Drug.legal_US
- Schedule I
- Drug.legal_UN
- P I
- Drug.legal_status
- SE: Förteckning I
via Wikipedia infobox
Chemical data
- Formula
- C9H11NO
- Molecular weight
- 149.19 g/mol
- IUPAC name
- (2S)-2-amino-1-phenylpropan-1-one
- SMILES
- C[C@@H](C(=O)C1=CC=CC=C1)N
- InChIKey
- PUAQLLVFLMYYJJ-ZETCQYMHSA-N
- XLogP
- 1.1
- Polar surface area
- 43.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
2,108 papers- Cathinone neurotoxicity ("The "3Ms").Current neuropharmacology · 2015
- Synthetic cathinone adulteration of illegal drugs.Psychopharmacology · 2019
- DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants.ACS chemical neuroscience · 2018
- Neurotoxicology of Synthetic Cathinone Analogs.Current topics in behavioral neurosciences · 2017
- Synthetic cathinone abuse.Clinical pharmacology : advances and applications · 2013
via PubMed
Wikidata facts
- Mass
- 149.084
Show 5 more facts
- chemical formula
- C₉H₁₁NO
- canonical SMILES
- CC(C(=O)C1=CC=CC=C1)N
- isomeric SMILES
- C[C@@H](C(=O)C1=CC=CC=C1)N
- World Health Organisation international non-proprietary name
- cathinone
- Commons category
- Cathinone
via Wikidata · CC0
~17 min read
Article
15 sectionsContents
- History
- Discovery
- Cultural significance
- Legality
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Effects on health
- Chemistry
- Biosynthesis
- Synthetic production
- Structure
- See also
- References
- External links
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.
==History== ===Discovery=== 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 evidence of a different alkaloid, cathinone. Cathinone is molecularly similar to cathine, but is much more abundant in younger plants. This finding caused scientists to speculate that cathinone was the true active ingredient in khat.