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

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
Synthesis of enantiopure homoallylic ethers by reagent controlled facial selective allylation of chiral ketones.
2001 Jan 5
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.
2001 Sep
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.
2001 Sep 5
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.
2002 Jun
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
2002 Oct
Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers.
2003 Apr 23
The use of cyclohexanone as a "derivatizing" reagent for the GC-MS detection of amphetamines and ephedrines in seizures and the urine.
2003 Jul 29
Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction.
2003 Jul 5
Determination of ephedrine alkaloids in dietary supplements and botanicals by liquid chromatography/tandem mass spectrometry: collaborative study.
2003 Jul-Aug
Separation and quantitation of the stereoisomers of ephedra alkaloids in natural health products using flow injection-electrospray ionization-high field asymmetric waveform ion mobility spectrometry-mass spectrometry.
2003 Jun 1
Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule.
2003 May 1
In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates.
2003 Oct
Analysis of ephedra-alkaloids using sweeping and cation-selective exhaustive injection and sweeping micellar electrokinetic chromatography methods.
2004 Feb
Determination of ephedra alkaloids in urine and plasma by HPLC-UV: collaborative study.
2004 Jan-Feb
Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat.
2004 Jun
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
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
A rapid and simple procedure for the determination of ephedrine alkaloids in dietary supplements by gas chromatography-mass spectrometry.
2006 Aug 28
Stability studies of amphetamine and ephedrine derivatives in urine.
2006 Oct 20
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.
2007 Feb
Cathine, an amphetamine-related compound, acts on mammalian spermatozoa via beta1- and alpha2A-adrenergic receptors in a capacitation state-dependent manner.
2007 Mar
[Khat--a new drug of abuse in Norway].
2007 Mar 1
Simultaneous chiral separation of ephedrine alkaloids by MEKC-ESI-MS using polymeric surfactant II: application in dietary supplements.
2007 May
Miscellaneous.
2008 Oct
Khat - a controversial plant.
2009
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
Problems of the use of pseudoephedrine by athletes.
2009 Aug
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.
2009 Aug 23
Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis.
2009 Dec 5
Development and validation of an LC-MS/MS method for the quantification of ephedrines in urine.
2009 Feb 1
The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.
2009 Feb 17
Qualitative confirmation procedure for ephedrines as acetonide derivatives in doping urine samples by gas chromatography/electron ionization mass spectrometry.
2009 Jan
Keep an eye on the pupil: developing countries under chemical attack.
2009 Jun
Extraction and microencapsulation of khat: effects on sexual motivation and estradiol level in female rats.
2009 Mar
Interpretation of urinary concentrations of pseudoephedrine and its metabolite cathine in relation to doping control.
2009 May
Time for a "Third Wave" of malaria activism to tackle the drug stock-out crisis.
2009 Nov
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
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
Khat use and monitoring drug use in Europe: the current situation and issues for the future.
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
Fast analysis of doping agents in urine by ultra-high-pressure liquid chromatography-quadrupole time-of-flight mass spectrometry. II: Confirmatory analysis.
2010 Jun 18
Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine.
2010 May
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

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 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
NCI_THESAURUS C221
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
WHO-ATC A08AA07
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
DEA NO. 1230
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
Code System Code Type Description
RXCUI
32022
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID50889347
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
DRUG CENTRAL
3389
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
WIKIPEDIA
CATHINE
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
PUBCHEM
441457
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
MERCK INDEX
m8073
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C79914
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
CAS
492-39-7
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL1412041
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PRIMARY
FDA UNII
E1L4ZW2F8O
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PRIMARY
DRUG BANK
DB01486
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PRIMARY
MESH
C005331
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
SMS_ID
100000081373
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
MERCK INDEX
m8687
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY Merck Index
INN
4952
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-754-1
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
EVMPD
SUB06158MIG
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY