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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
Neural degeneration following chronic stimulant abuse reveals a weak link in brain, fasciculus retroflexus, implying the loss of forebrain control circuitry.
2002 Aug
Effects of amphetamine derivatives and cathinone on noradrenaline-evoked contractions of rat right ventricle.
2002 Sep 20
Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers.
2003 Apr 23
Coronary and aortic vasoconstriction by cathinone, the active constituent of khat.
2003 Oct-Dec
MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the beta-position.
2004 Aug 1
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
Methcathinone: a new postindustrial drug.
2005 Oct 4
Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry.
2007
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).
2007 Dec 3
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
Modulation of cholinergic contractions of airway smooth muscle by cathinone: potential beneficial effects in airway diseases.
2008 Sep
Khat - a controversial plant.
2009
[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
Long-term effects of chronic khat use: impaired inhibitory control.
2010
Khat chewing, cardiovascular diseases and other internal medical problems: the current situation and directions for future research.
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
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

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
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USP
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ACTIVE MOIETY