Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11NO |
Molecular Weight | 149.1897 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](N)C(=O)C1=CC=CC=C1
InChI
InChIKey=PUAQLLVFLMYYJJ-ZETCQYMHSA-N
InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1
Cathinone is one of the biologically active alkaloids found in the khat shrub (Catha edulis). Due to its psychoactive properties, khat has been known and utilized for ages by the inhabitants of East Africa and the northeastern parts of Arabian Peninsula. In many regions, chewing of freshly collected khat leaves (thus liberating cathinone, which affects the central nervous system) is considered a matter of culture and local tradition. Because of their structural similarity to amphetamine, cathinone and its analogs are often denoted as “natural amphetamines”, and the only structural difference between amphetamine and cathinone is the presence of a carbonyl group in the α-position of cathinone’s side chain. Similar to amphetamine, cathinone and its analogs are characterized by stimulating, euphoric, and empathogenic properties. Due to their effects on the central nervous system, the first synthetic cathinone derivatives were synthesized for medicinal purposes in the early twentieth century, but they began attracting wider attention around the year 2000. At that time, synthetic cathinones were included in a broader group of psychoactive compounds denoted as “legal drugs” or “designer drugs”
Originator
Approval Year
PubMed
Title | Date | PubMed |
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The subjective effects of chewing Qat leaves in human volunteers. | 2002 Jan-Mar |
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Actions of amphetamine derivatives and cathinone at the noradrenaline transporter. | 2003 Aug 22 |
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Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometry. | 2003 Nov 5 |
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In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. | 2003 Oct |
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Coronary and aortic vasoconstriction by cathinone, the active constituent of khat. | 2003 Oct-Dec |
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MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the beta-position. | 2004 Aug 1 |
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Driving under the influence of khat--alkaloid concentrations and observations in forensic cases. | 2004 Feb 10 |
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Khat habit and its health effect. A natural amphetamine. | 2004 Jul |
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A study of 342 oral keratotic white lesions induced by qat chewing among 2500 Yemeni. | 2004 Jul |
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Khat (Catha edulis)-induced apoptosis is inhibited by antagonists of caspase-1 and -8 in human leukaemia cells. | 2004 Nov 1 |
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Catha edulis: a new differential in the diagnosis of pregnancy induced hypertension. | 2004 Oct |
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Liquid chromatographic enantioseparation of aryl alpha-amino ketones on a crown ether-based chiral stationary phase. | 2005 Apr |
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Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia. | 2005 Feb 12 |
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Khat and alcohol use and risky sex behaviour among in-school and out-of-school youth in Ethiopia. | 2005 Oct 14 |
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Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine. | 2006 Jun |
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Catha edulis extract and its active principle cathinone induce ipsilateral rotation in unilaterally lesioned rats. | 2006 Nov |
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The consumption of khat and other drugs in Somali combatants: a cross-sectional study. | 2007 Dec |
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Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.). | 2007 Dec 3 |
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[Khat--a new drug of abuse in Norway]. | 2007 Mar 1 |
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Khat (Catha edulis): health aspects of khat chewing. | 2007 May-Jun |
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Liquid chromatography-tandem mass spectrometry method for the simultaneous analysis of multiple hallucinogens, chlorpheniramine, ketamine, ritalinic acid, and metabolites, in urine. | 2007 Oct |
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Factors predisposing out-of-school youths to HIV/AIDS-related risky sexual behaviour in northwest Ethiopia. | 2007 Sep |
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Khat chewing from the pharmacological point of view: an update. | 2008 |
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Phylogeny of the Celastreae (Celastraceae) and the relationships of Catha edulis (qat) inferred from morphological characters and nuclear and plastid genes. | 2008 Aug |
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Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order. | 2008 Dec |
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The perioperative implications of khat use. | 2008 Feb |
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Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006. | 2008 Jul |
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Half a gram--a thousand lives. | 2008 Jun 24 |
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Illicit cathinone ("Hagigat") poisoning. | 2008 Mar |
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The effect of Khat (Catha edulis) as an appetite suppressant is independent of ghrelin and PYY secretion. | 2008 Nov |
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Liquid chromatographic direct resolution of aryl alpha-amino ketones on a residual silanol group-protecting chiral stationary phase based on optically active (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6. | 2008 Nov 1 |
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Modulation of cholinergic contractions of airway smooth muscle by cathinone: potential beneficial effects in airway diseases. | 2008 Sep |
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Khat - a controversial plant. | 2009 |
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Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic. | 2009 Aug 23 |
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Rapid GC-MS confirmation of amphetamines in urine by extractive acylation. | 2009 Jan 10 |
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Keep an eye on the pupil: developing countries under chemical attack. | 2009 Jun |
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[Drugs and desperation in different worlds. Abuse of cathinone and methcathinone]. | 2009 May 13-19 |
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Long-term effects of chronic khat use: impaired inhibitory control. | 2010 |
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LC-MS/MS screening method for designer amphetamines, tryptamines, and piperazines in serum. | 2010 Apr |
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Analyses of second-generation 'legal highs' in the UK: initial findings. | 2010 Aug |
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Khat use and neurobehavioral functions: suggestions for future studies. | 2010 Dec 1 |
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Khat use and monitoring drug use in Europe: the current situation and issues for the future. | 2010 Dec 1 |
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Khat in the Horn of Africa: historical perspectives and current trends. | 2010 Dec 1 |
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Cathinone preservation in khat evidence via drying. | 2010 Feb 25 |
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Olanzapine and pulmonary embolism, a rare association: a case report. | 2010 Jan 22 |
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Purchasing 'legal highs' on the Internet--is there consistency in what you get? | 2010 Jul |
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Regular Khat (Catha edulis) chewing is associated with elevated diastolic blood pressure among adults in Butajira, Ethiopia: a comparative study. | 2010 Jul 2 |
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Mephedrone use and associated adverse effects in school and college/university students before the UK legislation change. | 2010 Nov |
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Motives for khat use and abstinence in Yemen--a gender perspective. | 2010 Nov 27 |
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Recreational use of mephedrone (4-methylmethcathinone, 4-MMC) with associated sympathomimetic toxicity. | 2010 Sep |
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Classification Tree | Code System | Code | ||
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DEA NO. |
1235
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CHEMBL2104047
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540EI4406J
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C166812
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SUB06159MIG
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C023665
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DTXSID0050427
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4110
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m3177
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62258
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CATHINONE
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PC 010
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100000081354
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4953
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DB01560
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71031-15-7
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)