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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO.ClH
Molecular Weight 185.651
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CATHINONE HYDROCHLORIDE

SMILES

Cl.C[C@H](N)C(=O)C1=CC=CC=C1

InChI

InChIKey=HPZCAKYHISJOIK-FJXQXJEOSA-N
InChI=1S/C9H11NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7H,10H2,1H3;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Re: cathinone: a new differential in the diagnosis of pregnancy induced hypertension.
2004 Aug
Khat habit and its health effect. A natural amphetamine.
2004 Jul
Catha edulis: a new differential in the diagnosis of pregnancy induced hypertension.
2004 Oct
Herbal ecstasy: cardiovascular complications of khat chewing in pregnancy.
2005
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
The potential adverse effects of habitual use of Catha edulis (khat).
2005 Nov
Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine.
2006 Jun
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).
2007 Dec 3
Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats.
2007 May
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
Factors predisposing out-of-school youths to HIV/AIDS-related risky sexual behaviour in northwest Ethiopia.
2007 Sep
Phylogeny of the Celastreae (Celastraceae) and the relationships of Catha edulis (qat) inferred from morphological characters and nuclear and plastid genes.
2008 Aug
Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006.
2008 Jul
Modulation of cholinergic contractions of airway smooth muscle by cathinone: potential beneficial effects in airway diseases.
2008 Sep
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.
2009 Aug 23
Long-term effects of chronic khat use: impaired inhibitory control.
2010
Analyses of second-generation 'legal highs' in the UK: initial findings.
2010 Aug
Cathinone preservation in khat evidence via drying.
2010 Feb 25
Olanzapine and pulmonary embolism, a rare association: a case report.
2010 Jan 22
Mephedrone use and associated adverse effects in school and college/university students before the UK legislation change.
2010 Nov
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:10:14 GMT 2023
Edited
by admin
on Fri Dec 15 16:10:14 GMT 2023
Record UNII
272NNG64V6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CATHINONE HYDROCHLORIDE
INCB:GREEN LIST   MI  
Common Name English
1-PROPANONE, 2-AMINO-1-PHENYL-, HYDROCHLORIDE, (2S)-
Systematic Name English
(S)-(-)-CATHINONE HYDROCHLORIDE
Common Name English
CATHINONE HYDROCHLORIDE S-FORM [MI]
Common Name English
CATHINONE HYDROCHLORIDE, (-)-
Common Name English
CATHINONE HYDROCHLORIDE [INCB GREEN LIST]
Common Name English
CATHINONE HYDROCHLORIDE [USP-RS]
Common Name English
Code System Code Type Description
INCB IDS CODE
PC 010
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
CAS
72739-14-1
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
RS_ITEM_NUM
1096804
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
FDA UNII
272NNG64V6
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
MERCK INDEX
m3177
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID8048866
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
PUBCHEM
11956149
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
MESH
C023665
Created by admin on Fri Dec 15 16:10:14 GMT 2023 , Edited by admin on Fri Dec 15 16:10:14 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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IMPURITY (UV)
USP
Related Record Type Details
ACTIVE MOIETY