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 |
|---|---|---|
| Khat chewing, cardiovascular diseases and other internal medical problems: the current situation and directions for future research. | 2010-12-01 |
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| Khat use and neurobehavioral functions: suggestions for future studies. | 2010-12-01 |
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| Khat use and monitoring drug use in Europe: the current situation and issues for the future. | 2010-12-01 |
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| Khat in the Horn of Africa: historical perspectives and current trends. | 2010-12-01 |
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| Motives for khat use and abstinence in Yemen--a gender perspective. | 2010-11-27 |
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| Association of khat chewing with increased risk of stroke and death in patients presenting with acute coronary syndrome. | 2010-11 |
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| Mephedrone use and associated adverse effects in school and college/university students before the UK legislation change. | 2010-11 |
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| Recreational use of mephedrone (4-methylmethcathinone, 4-MMC) with associated sympathomimetic toxicity. | 2010-09 |
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| Analyses of second-generation 'legal highs' in the UK: initial findings. | 2010-08 |
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| Regular Khat (Catha edulis) chewing is associated with elevated diastolic blood pressure among adults in Butajira, Ethiopia: a comparative study. | 2010-07-02 |
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| Purchasing 'legal highs' on the Internet--is there consistency in what you get? | 2010-07 |
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| LC-MS/MS screening method for designer amphetamines, tryptamines, and piperazines in serum. | 2010-04 |
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| The vascular effects of trace amines and amphetamines. | 2010-03 |
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| Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010-02-25 |
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| Cathinone preservation in khat evidence via drying. | 2010-02-25 |
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| Olanzapine and pulmonary embolism, a rare association: a case report. | 2010-01-22 |
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| Long-term effects of chronic khat use: impaired inhibitory control. | 2010 |
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| Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis. | 2010 |
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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. | 2009-11-13 |
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| Use of khat and posttraumatic stress disorder as risk factors for psychotic symptoms: a study of Somali combatants. | 2009-10 |
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| Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic. | 2009-08-23 |
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| [Drugs and desperation in different worlds. Abuse of cathinone and methcathinone]. | 2009-07-10 |
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| Boltushka: a homemade amphetamine-type stimulant and HIV risk in Odessa, Ukraine. | 2009-07 |
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| Prevalence of Khat chewing in college and secondary (high) school students of Jazan region, Saudi Arabia. | 2009-06-20 |
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| Keep an eye on the pupil: developing countries under chemical attack. | 2009-06 |
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| Proconvulsant effect of khat (Catha edulis) in Sprague dawley rats. | 2009-01-30 |
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| Qat and its health effects. | 2009-01-10 |
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| Rapid GC-MS confirmation of amphetamines in urine by extractive acylation. | 2009-01-10 |
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| Khat - a controversial plant. | 2009 |
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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. | 2008-12 |
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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. | 2008-11-01 |
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| The effect of Khat (Catha edulis) as an appetite suppressant is independent of ghrelin and PYY secretion. | 2008-11 |
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| Modulation of cholinergic contractions of airway smooth muscle by cathinone: potential beneficial effects in airway diseases. | 2008-09 |
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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. | 2008-08 |
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| A review of the neuropharmacological properties of khat. | 2008-07-01 |
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| Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006. | 2008-07 |
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| Half a gram--a thousand lives. | 2008-06-24 |
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| Illicit cathinone ("Hagigat") poisoning. | 2008-03 |
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| The perioperative implications of khat use. | 2008-02 |
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| Khat chewing from the pharmacological point of view: an update. | 2008 |
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| Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.). | 2007-12-03 |
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| The consumption of khat and other drugs in Somali combatants: a cross-sectional study. | 2007-12 |
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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. | 2007-10 |
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| Factors predisposing out-of-school youths to HIV/AIDS-related risky sexual behaviour in northwest Ethiopia. | 2007-09 |
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| Khat (Catha edulis): health aspects of khat chewing. | 2007-08-11 |
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| Vasoconstriction of porcine left anterior descending coronary artery by ecstasy and cathinone is not an indirect sympathomimetic effect. | 2007-07 |
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| Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats. | 2007-05 |
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| [Khat--a new drug of abuse in Norway]. | 2007-03-01 |
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| Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry. | 2007 |
|
| Oral white lesions associated with chewing khat. | 2004-09-15 |
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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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m3177
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62258
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CATHINONE
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PC 010
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71031-15-7
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)