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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Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure. | 2001 Oct |
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Neural degeneration following chronic stimulant abuse reveals a weak link in brain, fasciculus retroflexus, implying the loss of forebrain control circuitry. | 2002 Aug |
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The subjective effects of chewing Qat leaves in human volunteers. | 2002 Jan-Mar |
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The effect of chewing Khat leaves on human mood. | 2002 Jul |
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Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing. | 2002 Oct |
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Actions of amphetamine derivatives and cathinone at the noradrenaline transporter. | 2003 Aug 22 |
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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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Re: cathinone: a new differential in the diagnosis of pregnancy induced hypertension. | 2004 Aug |
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Driving under the influence of khat--alkaloid concentrations and observations in forensic cases. | 2004 Feb 10 |
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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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Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia. | 2005 Feb 12 |
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Behavioural sensitisation following repeated intermittent oral administration of Catha edulis in rats. | 2005 Jan 30 |
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Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine. | 2006 Jun |
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Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry. | 2007 |
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Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization. | 2007 Feb |
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Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats. | 2007 May |
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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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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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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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A review of the neuropharmacological properties of khat. | 2008 Jul 1 |
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Illicit cathinone ("Hagigat") poisoning. | 2008 Mar |
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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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[Drugs and desperation in different worlds. Abuse of cathinone and methcathinone]. | 2009 May 13-19 |
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Camptothecin and khat (Catha edulis Forsk.) induced distinct cell death phenotypes involving modulation of c-FLIPL, Mcl-1, procaspase-8 and mitochondrial function in acute myeloid leukemia cell lines. | 2009 Nov 13 |
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Use of khat and posttraumatic stress disorder as risk factors for psychotic symptoms: a study of Somali combatants. | 2009 Oct |
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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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Khat use and monitoring drug use in Europe: the current situation and issues for the future. | 2010 Dec 1 |
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Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010 Feb 25 |
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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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Recreational use of mephedrone (4-methylmethcathinone, 4-MMC) with associated sympathomimetic toxicity. | 2010 Sep |
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Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis. | 2010 Winter |
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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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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)