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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO
Molecular Weight 151.2056
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CATHINE

SMILES

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

InChI

InChIKey=DLNKOYKMWOXYQA-IONNQARKSA-N
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_14.htm | https://www.standort-ludwigshafen.basf.de/group/corporate/site-ludwigshafen/en/brand/CATHINE_HYDROCHLORIDE

Cathine, known as D-norpseudoephedrine, is a psychoactive drug of amphetamine class, found naturally in Catha edulis (khat). It is a norepinephrine and dopamine releasing agent, and has thermogenic and anorectic effect. In the United States, cathine is classified as a Schedule IV controlled substance. Cathine hydrochloride is used as an appetite suppressant during the first few weeks of dieting to help establish new eating habits.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CATHINE HYDROCHLORIDE

Approved Use

Treatment of obesity
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
2003 Jul
Determination of ephedrine alkaloids in human urine and plasma by liquid chromatography/tandem mass spectrometry: collaborative study.
2003 Jul-Aug
Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule.
2003 May 1
Determination of ephedrine alkaloids and synephrine in dietary supplements by column-switching cation exchange high-performance liquid chromatography with scanning-wavelength ultraviolet and fluorescence detection.
2003 Sep 10
Determination of ephedra alkaloid and caffeine concentrations in dietary supplements and biological fluids.
2004 Apr
Concentrations of ephedra alkaloids and caffeine in commercial dietary supplements.
2004 Apr
Driving under the influence of khat--alkaloid concentrations and observations in forensic cases.
2004 Feb 10
Determination of ephedra alkaloids in urine and plasma by HPLC-UV: collaborative study.
2004 Jan-Feb
Reference materials for analytical toxicology including doping control: freeze-dried urine samples.
2004 May
One internal standard for multiple analytes: a limit and solution.
2004 Sep-Oct
Common drugs of abuse--Part II.
2004 Spring
Simultaneous quantification of six ephedrines in a Mahwang preparation and in urine by high-performance liquid chromatography.
2005 Jun
A rapid and simple procedure for the determination of ephedrine alkaloids in dietary supplements by gas chromatography-mass spectrometry.
2006 Aug 28
Electron ionization mass spectra of ephedrines in a doping confirmatory procedure: a curious migration of the trimethylsilyl group in the N-acetyl-O-trimethylsilyl derivatives.
2007
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).
2007 Dec 3
Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order.
2008 Dec
Miscellaneous.
2008 Oct
Elimination of ephedrines in urine following administration of a Sho-seiryu-to preparation.
2009 Apr
The relevance of the urinary concentration of ephedrines in anti-doping analysis: determination of pseudoephedrine, cathine, and ephedrine after administration of over-the-counter medicaments.
2009 Aug
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.
2009 Aug 23
The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.
2009 Feb 17
Keep an eye on the pupil: developing countries under chemical attack.
2009 Jun
Interpretation of urinary concentrations of pseudoephedrine and its metabolite cathine in relation to doping control.
2009 May
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
Influence of triiodothyronine on the contractile effect of D-nor-pseudoephedrine.
2010
Long-term effects of chronic khat use: impaired inhibitory control.
2010
Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine.
2010 May
Patents

Sample Use Guides

As a component of khat, cathine is administered by chewing khat leaves. As a dietary supplement, cathine hydrochloride is administered orally, 20-50 mg once daily after breakfast for up to 4 wk. It is also available as oral drops.
Route of Administration: Oral
For the NE release assay, whole rat brain minus cerebellum and caudate was homogenized in ice-cold 10% sucrose containing 1 uM reserpine. 50 nM GBR12935 and 100 nM citalopram were added to block [3H]MPP uptake into DA and 5-HT nerves. After 12 strokes with a Potter-Elvehjem homogenizer, brain homogenates were centrifuged at 1,000g for 10 min at 0–4°C, and the supernatants were retained on ice. Synaptosomal preparations were incubated to steady state with 5 nM [3H]MPP in a Krebs-phosphate buffer. After incubation to steady state, 850uL of synaptosomes preloaded with 3H ligand was added to test tubes that contained 150 uL of test drug. The release reaction was terminated by dilution with 4 ml of wash buffer followed by rapid vacuum filtration over GF/B filters. Retained tritium was counted by a liquid scintillation counter. L-Norpseudoephedrine was able to evoke NE release with EC50 of 15 nM.
Name Type Language
CATHINE
INN   MART.   WHO-DD  
INN  
Official Name English
CATHINUM
Common Name English
NORPSEUDOEPHEDRINE [MI]
Common Name English
Cathine [WHO-DD]
Common Name English
(1S,2S)-PSEUDONOREPHEDRINE
Common Name English
NORPSEUDOEPHEDRINE, D-
Common Name English
cathine [INN]
Common Name English
(1S,2S)-(+)-NORPSEUDOEPHEDRINE
Common Name English
PHENYLPROPANOLAMINE D-THREO-FORM [MI]
Common Name English
THREO-2-AMINO-1-PHENYLPROPAN-1-OL
Common Name English
BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-, (.ALPHA.S)-
Common Name English
CATINA
Common Name English
(1S,2S)-2-AMINO-1-PHENYL-1-PROPANOL
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, (S-(R*,R*))-
Common Name English
(+)-NORPSEUDOEPHEDRINE
Common Name English
D-(+)-NORPSEUDOEPHEDRINE
Common Name English
CATHINE [MART.]
Common Name English
(1S,2S)-2-AMINO-1-PHENYLPROPAN-1-OL
Common Name English
Classification Tree Code System Code
WHO-VATC QA08AA07
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
NCI_THESAURUS C221
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
WHO-ATC A08AA07
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
DEA NO. 1230
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
Code System Code Type Description
RXCUI
32022
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID50889347
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
DRUG CENTRAL
3389
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
WIKIPEDIA
CATHINE
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
PUBCHEM
441457
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
MERCK INDEX
m8073
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C79914
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
CAS
492-39-7
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL1412041
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
FDA UNII
E1L4ZW2F8O
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
DRUG BANK
DB01486
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
MESH
C005331
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
SMS_ID
100000081373
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
MERCK INDEX
m8687
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY Merck Index
INN
4952
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-754-1
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY
EVMPD
SUB06158MIG
Created by admin on Fri Dec 15 17:40:21 UTC 2023 , Edited by admin on Fri Dec 15 17:40:21 UTC 2023
PRIMARY