Cathinone

Cathinone
Systematic (IUPAC) name
(S)-2-Amino-1-phenyl-1-propanone
Clinical data
Pharmacokinetic data
Half-life 0.7–2.3 h[1]
Identifiers
71031-15-7 Yes
None
PubChem CID 62258
DrugBank DB01560 Yes
ChemSpider 56062 Yes
UNII 540EI4406J Yes
KEGG C08301 Yes
ChEBI CHEBI:4110 Yes
ChEMBL CHEMBL2104047 
Chemical data
Formula C9H11NO
149.19 g/mol
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Cathinone /ˈkæθɨnoʊn/ (also known as benzoylethanamine, or β-keto-amphetamine also known as hagigat (Hebrew: חגיגת‎ "celebration") 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. 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.

Legality

Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances.[3] 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.[4][5][6]

Pharmacology

Cathinone induces the release of dopamine from freshly-killed rabbit brain striatal preparations that are prelabelled either with dopamine or its precursors.[7]

Chemistry

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.[8]

Racemic cathinone from propiophenone via the α-brominated intermediate

See also

References

  1. ↑ Toennes SW, Harder S, Schramm M, Niess C, Kauert GF (2003). "Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves". Br J Clin Pharmacol 56 (1): 125–130. doi:10.1046/j.1365-2125.2003.01834.x. PMC 1884326. PMID 12848785.
  2. ↑ Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B (2008). "Illicit cathinone ("Hagigat") poisoning". Clin Toxicol (Phila) 46 (3): 206–10. doi:10.1080/15563650701517574. PMID 17852166.
  3. ↑ "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. United Nations. 2003. Archived from the original (PDF) on 2012-08-31.
  4. ↑ "Synthetic Street Drug Camouflaged as Bath Salts Has Dangerous, Bizarre Effects". PBS NewsHour. 20 September 2012. Retrieved 7 December 2013.
  5. ↑ The Guardian: Drugs and dance as Israelis blot out intifada | World news | The Guardian, accessdate: 4/19/2015
  6. ↑ National | Globalnews.ca: What you need to know about flakka, the latest drug causing erratic behaviour - National | Globalnews.ca, accessdate: 4/19/2015
  7. ↑ 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.
  8. ↑ 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