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
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
Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure.
2001 Oct
Neural degeneration following chronic stimulant abuse reveals a weak link in brain, fasciculus retroflexus, implying the loss of forebrain control circuitry.
2002 Aug
The effect of chewing Khat leaves on human mood.
2002 Jul
Effects of amphetamine derivatives and cathinone on noradrenaline-evoked contractions of rat right ventricle.
2002 Sep 20
Actions of amphetamine derivatives and cathinone at the noradrenaline transporter.
2003 Aug 22
In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates.
2003 Oct
MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the beta-position.
2004 Aug 1
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
Methcathinone: a new postindustrial drug.
2005 Oct 4
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).
2007 Dec 3
Khat (Catha edulis): health aspects of khat chewing.
2007 May-Jun
Liquid chromatography-tandem mass spectrometry method for the simultaneous analysis of multiple hallucinogens, chlorpheniramine, ketamine, ritalinic acid, and metabolites, in urine.
2007 Oct
Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order.
2008 Dec
The effect of Khat (Catha edulis) as an appetite suppressant is independent of ghrelin and PYY secretion.
2008 Nov
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
Rapid GC-MS confirmation of amphetamines in urine by extractive acylation.
2009 Jan 10
Proconvulsant effect of khat (Catha edulis) in Sprague dawley rats.
2009 Jan 30
[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
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
Purchasing 'legal highs' on the Internet--is there consistency in what you get?
2010 Jul
The vascular effects of trace amines and amphetamines.
2010 Mar
Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis.
2010 Winter
Patents

Patents

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 Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2104047
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
FDA UNII
540EI4406J
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
NCI_THESAURUS
C166812
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
EVMPD
SUB06159MIG
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
MESH
C023665
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
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EPA CompTox
DTXSID0050427
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
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CHEBI
4110
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
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MERCK INDEX
m3177
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY Merck Index
PUBCHEM
62258
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
WIKIPEDIA
CATHINONE
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
INCB IDS CODE
PC 010
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
SMS_ID
100000081354
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
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INN
4953
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
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DRUG BANK
DB01560
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
PRIMARY
CAS
71031-15-7
Created by admin on Sat Dec 16 17:18:28 GMT 2023 , Edited by admin on Sat Dec 16 17:18:28 GMT 2023
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