U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CATHINONE

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

HIDE SMILES / InChI

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

Sources: Experientia (1979), 35, (5), 572-4.

Approval Year

PubMed

PubMed

TitleDatePubMed
The subjective effects of chewing Qat leaves in human volunteers.
2002 Jan-Mar
Actions of amphetamine derivatives and cathinone at the noradrenaline transporter.
2003 Aug 22
Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
2003 Jul
Coronary and aortic vasoconstriction by cathinone, the active constituent of khat.
2003 Oct-Dec
Anticataleptic activity of cathinone and MDMA (Ecstasy) upon acute and subchronic administration in rat.
2003 Sep 15
Re: cathinone: a new differential in the diagnosis of pregnancy induced hypertension.
2004 Aug
MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the beta-position.
2004 Aug 1
Khat habit and its health effect. A natural amphetamine.
2004 Jul
A study of 342 oral keratotic white lesions induced by qat chewing among 2500 Yemeni.
2004 Jul
Khat (Catha edulis)-induced apoptosis is inhibited by antagonists of caspase-1 and -8 in human leukaemia cells.
2004 Nov 1
Oral white lesions associated with chewing khat.
2004 Sep 15
Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia.
2005 Feb 12
Behavioural sensitisation following repeated intermittent oral administration of Catha edulis in rats.
2005 Jan 30
Khat chewing is a risk factor for acute myocardial infarction: a case-control study.
2005 May
Clozapine attenuates the locomotor sensitisation and the prepulse inhibition deficit induced by a repeated oral administration of Catha edulis extract and cathinone in rats.
2005 May 28
The potential adverse effects of habitual use of Catha edulis (khat).
2005 Nov
Khat and alcohol use and risky sex behaviour among in-school and out-of-school youth in Ethiopia.
2005 Oct 14
Catha edulis extract and its active principle cathinone induce ipsilateral rotation in unilaterally lesioned rats.
2006 Nov
Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry.
2007
The consumption of khat and other drugs in Somali combatants: a cross-sectional study.
2007 Dec
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.
2007 Feb
[Khat--a new drug of abuse in Norway].
2007 Mar 1
Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats.
2007 May
Liquid chromatography-tandem mass spectrometry method for the simultaneous analysis of multiple hallucinogens, chlorpheniramine, ketamine, ritalinic acid, and metabolites, in urine.
2007 Oct
Factors predisposing out-of-school youths to HIV/AIDS-related risky sexual behaviour in northwest Ethiopia.
2007 Sep
Khat chewing from the pharmacological point of view: an update.
2008
Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order.
2008 Dec
The perioperative implications of khat use.
2008 Feb
A review of the neuropharmacological properties of khat.
2008 Jul 1
Illicit cathinone ("Hagigat") poisoning.
2008 Mar
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
Khat - a controversial plant.
2009
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.
2009 Aug 23
Rapid GC-MS confirmation of amphetamines in urine by extractive acylation.
2009 Jan 10
Boltushka: a homemade amphetamine-type stimulant and HIV risk in Odessa, Ukraine.
2009 Jul
Prevalence of Khat chewing in college and secondary (high) school students of Jazan region, Saudi Arabia.
2009 Jun 20
[Drugs and desperation in different worlds. Abuse of cathinone and methcathinone].
2009 May 13-19
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
Use of khat and posttraumatic stress disorder as risk factors for psychotic symptoms: a study of Somali combatants.
2009 Oct
Long-term effects of chronic khat use: impaired inhibitory control.
2010
Analyses of second-generation 'legal highs' in the UK: initial findings.
2010 Aug
Khat use and monitoring drug use in Europe: the current situation and issues for the future.
2010 Dec 1
Khat in the Horn of Africa: historical perspectives and current trends.
2010 Dec 1
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
Cathinone preservation in khat evidence via drying.
2010 Feb 25
Purchasing 'legal highs' on the Internet--is there consistency in what you get?
2010 Jul
Association of khat chewing with increased risk of stroke and death in patients presenting with acute coronary syndrome.
2010 Nov
Mephedrone use and associated adverse effects in school and college/university students before the UK legislation change.
2010 Nov
Motives for khat use and abstinence in Yemen--a gender perspective.
2010 Nov 27
Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis.
2010 Winter
Patents

Patents

Substance Class Chemical
Created
by admin
on Thu Jul 06 22:42:14 UTC 2023
Edited
by admin
on Thu Jul 06 22:42:14 UTC 2023
Record UNII
540EI4406J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CATHINONE
INCB:GREEN LIST   INN   MART.   MI   WHO-DD  
INN  
Official Name English
CATHINONE [INCB:GREEN LIST]
Common Name English
(-)-.ALPHA.-AMINOPROPIOPHENONE
Systematic Name English
AMFETAMINE SULFATE IMPURITY C [EP IMPURITY]
Common Name English
(2S)-2-AMINO-1-PHENYL-1-PROPANONE
Systematic Name English
NOREPHEDRONE
Common Name English
(S)-2-AMINOPROPIOPHENONE
Systematic Name English
C08301
Code English
D-CATHINONE
Common Name English
J18.754B
Code English
Cathinone [WHO-DD]
Common Name English
CATHINONE [MI]
Common Name English
CATHINONE [MART.]
Common Name English
S-(-)-CATHINONE
Common Name English
1-PROPANONE, 2-AMINO-1-PHENYL-, (2S)-
Systematic Name English
CATHINONE [USP IMPURITY]
Common Name English
cathinone [INN]
Common Name English
Classification Tree Code System Code
DEA NO. 1235
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL2104047
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
FDA UNII
540EI4406J
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
NCI_THESAURUS
C166812
Created by admin on Thu Jul 06 22:42:15 UTC 2023 , Edited by admin on Thu Jul 06 22:42:15 UTC 2023
PRIMARY
EVMPD
SUB06159MIG
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
MESH
C023665
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID0050427
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
CHEBI
4110
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
MERCK INDEX
M3177
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY Merck Index
PUBCHEM
62258
Created by admin on Thu Jul 06 22:42:15 UTC 2023 , Edited by admin on Thu Jul 06 22:42:15 UTC 2023
PRIMARY
WIKIPEDIA
CATHINONE
Created by admin on Thu Jul 06 22:42:15 UTC 2023 , Edited by admin on Thu Jul 06 22:42:15 UTC 2023
PRIMARY
INCB IDS CODE
PC 010
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
SMS_ID
100000081354
Created by admin on Thu Jul 06 22:42:15 UTC 2023 , Edited by admin on Thu Jul 06 22:42:15 UTC 2023
PRIMARY
INN
4953
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
DRUG BANK
DB01560
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
CAS
71031-15-7
Created by admin on Thu Jul 06 22:42:14 UTC 2023 , Edited by admin on Thu Jul 06 22:42:14 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY