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
Molecular Formula | C9H11NO |
Molecular Weight | 149.1897 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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Oral white lesions associated with chewing khat. | 2004 Sep 15 |
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Role of instrumental learning in tolerance to cathinone hypophagia. | 2006 Apr |
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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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Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry. | 2007 |
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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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Vasoconstriction of porcine left anterior descending coronary artery by ecstasy and cathinone is not an indirect sympathomimetic effect. | 2007 Jul |
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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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A review of the neuropharmacological properties of khat. | 2008 Jul 1 |
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Half a gram--a thousand lives. | 2008 Jun 24 |
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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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Qat and its health effects. | 2009 Jan 10 |
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Rapid GC-MS confirmation of amphetamines in urine by extractive acylation. | 2009 Jan 10 |
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Proconvulsant effect of khat (Catha edulis) in Sprague dawley rats. | 2009 Jan 30 |
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Boltushka: a homemade amphetamine-type stimulant and HIV risk in Odessa, Ukraine. | 2009 Jul |
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Keep an eye on the pupil: developing countries under chemical attack. | 2009 Jun |
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Prevalence of Khat chewing in college and secondary (high) school students of Jazan region, Saudi Arabia. | 2009 Jun 20 |
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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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Analyses of second-generation 'legal highs' in the UK: initial findings. | 2010 Aug |
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Khat chewing, cardiovascular diseases and other internal medical problems: the current situation and directions for future research. | 2010 Dec 1 |
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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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Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010 Feb 25 |
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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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The vascular effects of trace amines and amphetamines. | 2010 Mar |
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Association of khat chewing with increased risk of stroke and death in patients presenting with acute coronary syndrome. | 2010 Nov |
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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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Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis. | 2010 Winter |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:18:27 GMT 2023
by
admin
on
Sat Dec 16 17:18:27 GMT 2023
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Record UNII |
540EI4406J
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Record Status |
Validated (UNII)
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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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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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