Cathinone
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| Systematic (IUPAC) name | |
| (S)-2-amino-1-phenyl-1-propanone | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule III (CA) Class C (UK) Schedule I (US) |
| Identifiers | |
| CAS number | 71031-15-7  |
| ATC code | None |
| PubChem | CID 62258 |
| DrugBank | DB01560 |
| ChemSpider | 56062 |
| UNII | 540EI4406J |
| KEGG | C08301 |
| ChEBI | CHEBI:4110 |
| Chemical data | |
| Formula | C9H11NO |
| Mol. mass | 149.19 g/mol |
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Cathinone, or benzoylethanamine (marketed as hagigat in Israel[1]), is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors.[2] 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.[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). Synthetic cathinone is also often used as the key ingredient of recreational drug mixes commonly known as 'bath salts' in the United States.[4]
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[edit] 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).
[edit] Toxic effects
Excessive cathinone usage can cause loss of appetite, anxiety, irritability, insomnia, hallucinations and panic attacks. Chronic abusers are at risk of developing personality disorders and of sustaining myocardial infarction.[5] Please note that the drug referred to in this article was actually the closely related mephedrone, a cathinone derivative which does not occur in nature. Mephedrone is more potent as a releasing agent of serotonin compared to cathinone or methcathinone, hence its use in party pills as a "legal" replacement for MDMA. Persons driving under the influence of the drug have had their serum or urine tested for the presence of cathinone and norephedrine, a major metabolite.[6]
[edit] See also
[edit] References
- ^ 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.
- ^ 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.
- ^ International Narcotics Control Board (2003). "List of psychotropic substances under international control" (pdf). United Nations. http://www.incb.org/pdf/e/list/green.pdf+.
- ^ http://www.pbs.org/newshour/bb/science/july-dec12/bathsalts_09-20.html
- ^ Levy A (2011-08-11), "Top BBC music producer, 53, who composed music for The Office found dead by wife after taking party drug meow meow", Daily Mail (London), http://www.dailymail.co.uk/news/article-2024424/BBC-presenter-53-died-heart-attack-taking-illegal-party-drug-meow-meow.html
- ^ Baselt RC (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Biomedical Publications. pp. 250-252. ISBN 0-9626523-7-7.
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This article needs additional citations for verification. (December 2007) |
[edit] External links
- Erowid Cathinone Vault
- Cathinone Popularity Soars in Israel
- Photos of cathinone before it is extracted from khat
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