Cathinone

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Cathinone
Cathinone2DACS.svg
Cathinone3DanJ.gif
Systematic (IUPAC) name
(S)-2-amino-1-phenyl-1-propanone
Clinical data
Legal status
Pharmacokinetic data
Half-life 0.7–2.3 h[1]
Identifiers
CAS number 71031-15-7 YesY
ATC code None
PubChem CID 62258
DrugBank DB01560
ChemSpider 56062 YesY
UNII 540EI4406J YesY
KEGG C08301 YesY
ChEBI CHEBI:4110 YesY
ChEMBL CHEMBL2104047
Chemical data
Formula C9H11NO 
Mol. mass 149.19 g/mol
 YesY (what is this?)  (verify)

Cathinone /ˈkæθɨnn/, benzoylethanamine, or β-ketone-amphetamine also known as hagigat (Hebrew: חגיגת‎) in Israel,[2] is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors.[3] 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 amphetamines that share this structure include the antidepressant bupropion and the stimulant methcathinone, among others.

Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances.[4] Circa 1993, the DEA added cathinone to the Controlled Substances Act's Schedule I.

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.[5]

Chemistry[edit]

The molecular structure of cathinone.

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. 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 having more psychoactive effects.

Cathinone can be extracted from Catha edulis, or synthesized from α-bromopropiophenone (which is easily made from propiophenone). Because cathinone is both a primary amine and a ketone, it is very likely to dimerize, especially as a free base isolated from plant matter.[6]

See also[edit]

References[edit]

  1. ^ Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.. Toennes SW, et al. (2003 Jul). Retrieved on 2014-01-30.
  2. ^ Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B (March 2008). "Illicit cathinone ("Hagigat") poisoning". Clin Toxicol (Phila) 46 (3): 206–10. doi:10.1080/15563650701517574. PMID 17852166. 
  3. ^ Kalix P (1981). "Cathinone, an alkaloid from khat leaves with an amphetamine-like releasing effect". Psychopharmacology (Berl.) 74 (3): 269–70. doi:10.1007/BF00427108. PMID 6791236. 
  4. ^ "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. United Nations. 2003. Archived from the original on 2012-08-31. 
  5. ^ "Synthetic Street Drug Camouflaged as Bath Salts Has Dangerous, Bizarre Effects". PBS NewsHour. 20 September 2012. Retrieved 7 December 2013. 
  6. ^ Shulgin, Alexander (7 December 2005). "4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin". Ask Dr. Shulgin Online. Retrieved 10 September 2013. 

External links[edit]