Cathinone

Structural formula
General
Non-proprietary name	Cathinone
other names	( S ) -2-amino-1-phenyl-1-propanone; ( S ) - (-) - cathinone;
Molecular formula	C 9 H 11 NO [( S ) -Cathinone] ; C 9 H 11 NO · HCl [( S ) -Cathinone · hydrochloride ] ;
External identifiers / databases
EC number	636-099-8
ECHA InfoCard	100.163.927
PubChem	62258
ChemSpider	56062
DrugBank	DB01560
Wikidata	Q414242
Drug information
Drug class	stimulant
properties
Molar mass	149.19 g · mol −1 [( S ) -Cathinone · hydrochloride]
Physical state	firmly
Melting point	189–190 ° C [( S ) -Cathinone · hydrochloride]
solubility	soluble in water and ethanol
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	400 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cathinone is an amphetamine and is one of the stimulants . However, it is chemically different from many other amphetamine derivatives because it has a ketone group . Structurally, cathinone is closely related to the antidepressant bupropion .

Occurrence and extraction

Cath shrub ( Catha edulis )

It is one of the alkaloids from the cath tree ( Catha edulis ) and the spindle tree plant Maytenus krukovii . The drug " Kath " is extracted from the plants , which is particularly common in East Africa and the Arabian Peninsula.

effect

Cathinone has both a stimulating and a local anesthetic and anorectic effect. This occurs about 20 minutes after ingestion and lasts for about two to four hours. Monoamine oxidase inhibition is also being discussed . High to toxic doses cause hyperactivity, confusion, disorders of the blood circulation with sometimes increased blood pressure as well as hyperthermia and convulsions .

Analytics

The reliable detection of cathinone and synthetic cathinone derivatives succeeds after adequate sample preparation , e.g. B. solid phase extraction from the various test materials and subsequent derivatization by using chromatographic methods, in particular by coupling with mass spectrometry .

Legal status

In the Federal Republic of Germany, cathinone is listed in Appendix 1 of the Narcotics Act and is therefore a "non-marketable narcotic drug". Internationally, the substance falls under the Convention on Psychotropic Substances . In the United States, too, the active ingredient is on Schedule I of the Controlled Substances Act .

Individual evidence

^ The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition. Merck & Co., Whitehouse Station, NJ, USA, 2006, ISBN 0-911910-00-X , pp. 311-312.
↑ ^a ^b ^c ^d data sheet S (-) - Cathinone hydrochloride from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
↑ SW Toennes, S. Harder, M. Schramm, C. Niess, GF Kauert : Pharmacokinetics of cathinone, Cathine and norephedrine after the chewing of khat leaves. Institute of Forensic Toxicology, University of Frankfurt , PMC 1884326 (free full text).
↑ JB Leikin, FP Palouček: poisoning and toxicology handbook. 4th edition. Informa Health Care, 2007, ISBN 978-1-4200-4479-9 , p. 889.
↑ ^a ^b Karel Valter, Philippe Arrizabalaga: Designer drugs directory. Elsevier, 1998, ISBN 0-444-20525-X , p. 133.
↑ N. Nic-Daeid, KA Savage, D. Ramsay, C. Holland, OB Sutcliffe: Development of gas chromatography-mass spectrometry (GC-MS) and other rapid screening methods for the analysis of 16 'legal high' cathinone derivatives. In: Sci Justice. 54 (1), Mar 2014, pp. 22-31. PMID 24438774
↑ X. Li, CE Uboh, LR Soma, Y. Liu, F. Guan, CR Aurand, DS Bell, Y. You, J. Chen, GA Maylin: Sensitive hydrophilic interaction liquid chromatography / tandem mass spectrometry method for rapid detection, quantification and confirmation of cathinone-derived designer drugs for doping control in equine plasma. In: Rapid Commun Mass Spectrom. 28 (2), 30 Jan 2014, pp. 217-229. PMID 24338970
↑ Hong WY, Ko YC, Lin MC, Wang PY, Chen YP, Chiueh LC, Shih DY, Chou HK, Cheng HF: Determination of Synthetic Cathinones in Urine Using Gas Chromatography-Mass Spectrometry Techniques. , J Anal Toxicol. 2016 Jan-Feb; 40 (1): 12-6, PMID 26410364
↑ Juris.de: BtMG Annex I (to Section 1 Paragraph 1) narcotics that are not marketable .
↑ International Narcotics Control Board: List of psychotropic substances under international control ( Memento of August 31, 2012 in the Internet Archive ) 23rd edition, August 2003.

[MERCK_Index-1] The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition. Merck & Co., Whitehouse Station, NJ, USA, 2006, ISBN 0-911910-00-X , pp. 311-312.

[Sigma-2] ta sheet S (-) - Cathinone hydrochloride from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).

[3] SW Toennes, S. Harder, M. Schramm, C. Niess, GF Kauert : Pharmacokinetics of cathinone, Cathine and norephedrine after the chewing of khat leaves. Institute of Forensic Toxicology, University of Frankfurt , PMC 1884326 (free full text).

[4] JB Leikin, FP Palouček: poisoning and toxicology handbook. 4th edition. Informa Health Care, 2007, ISBN 978-1-4200-4479-9 , p. 889.

[valter-5] Karel Valter, Philippe Arrizabalaga: Designer drugs directory. Elsevier, 1998, ISBN 0-444-20525-X , p. 133.

[6] N. Nic-Daeid, KA Savage, D. Ramsay, C. Holland, OB Sutcliffe: Development of gas chromatography-mass spectrometry (GC-MS) and other rapid screening methods for the analysis of 16 'legal high' cathinone derivatives. In: Sci Justice. 54 (1), Mar 2014, pp. 22-31. PMID 24438774

[7] X. Li, CE Uboh, LR Soma, Y. Liu, F. Guan, CR Aurand, DS Bell, Y. You, J. Chen, GA Maylin: Sensitive hydrophilic interaction liquid chromatography / tandem mass spectrometry method for rapid detection, quantification and confirmation of cathinone-derived designer drugs for doping control in equine plasma. In: Rapid Commun Mass Spectrom. 28 (2), 30 Jan 2014, pp. 217-229. PMID 24338970

[8] Hong WY, Ko YC, Lin MC, Wang PY, Chen YP, Chiueh LC, Shih DY, Chou HK, Cheng HF: Determination of Synthetic Cathinones in Urine Using Gas Chromatography-Mass Spectrometry Techniques. , J Anal Toxicol. 2016 Jan-Feb; 40 (1): 12-6, PMID 26410364

[9] Juris.de: BtMG Annex I (to Section 1 Paragraph 1) narcotics that are not marketable .

[10] International Narcotics Control Board: List of psychotropic substances under international control ( Memento of August 31, 2012 in the Internet Archive ) 23rd edition, August 2003.