Cathinone

Cathinone
Clinical data
Other names	β-Ketoamphetamine; Benzoylethanamine
Dependence; liability	Physical: no data Psychological: Low–moderate
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage I (Authorized scientific use only); UK: Class C; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Elimination half-life	0.7–2.3 h
Identifiers
	IUPAC name (S)-2-Amino-1-phenylpropan-1-one;
CAS Number	71031-15-7 ;
PubChem CID	62258;
DrugBank	DB01560 ;
ChemSpider	56062 ;
UNII	540EI4406J;
KEGG	C08301 ;
ChEBI	CHEBI:4110 ;
ChEMBL	ChEMBL2104047 ;
CompTox Dashboard (EPA)	DTXSID0050427 ;
ECHA InfoCard	100.163.927
Chemical and physical data
Formula	C9H11NO
Molar mass	149.193 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ccccc1)[C@@H](N)C;
	InChI InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1 ; Key:PUAQLLVFLMYYJJ-ZETCQYMHSA-N ;
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Cathinone (/ˈkæθɪnoʊn/; 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.

^ Hosseinian A, Vessally E, Bekhradnia A, Nejati K, Rahimpour G (31 October 2017). "Benzoylethanamine drug interaction with the AlN nanosheet, nanotube and nanocage: Density functional theory studies". Thin Solid Films. 640: 93–98. doi:10.1016/j.tsf.2017.08.049.
^ Nutt D, King LA, Blakemore C (March 2007). "Development of a rational scale to assess the harm of drugs of potential misuse". Lancet. 369 (9566): 1047–53. doi:10.1016/S0140-6736(07)60464-4. PMID 17382831. S2CID 5903121.
^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ Toennes SW, Harder S, Schramm M, Niess C, Kauert GF (July 2003). "Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves". British Journal of Clinical Pharmacology. 56 (1): 125–130. doi:10.1046/j.1365-2125.2003.01834.x. PMC 1884326. PMID 12848785.

[1] Hosseinian A, Vessally E, Bekhradnia A, Nejati K, Rahimpour G (31 October 2017). "Benzoylethanamine drug interaction with the AlN nanosheet, nanotube and nanocage: Density functional theory studies". Thin Solid Films. 640: 93–98. doi:10.1016/j.tsf.2017.08.049.

[2] Nutt D, King LA, Blakemore C (March 2007). "Development of a rational scale to assess the harm of drugs of potential misuse". Lancet. 369 (9566): 1047–53. doi:10.1016/S0140-6736(07)60464-4. PMID 17382831. S2CID 5903121.

[3] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[4] Toennes SW, Harder S, Schramm M, Niess C, Kauert GF (July 2003). "Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves". British Journal of Clinical Pharmacology. 56 (1): 125–130. doi:10.1046/j.1365-2125.2003.01834.x. PMC 1884326. PMID 12848785.

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