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
The subjective effects of chewing Qat leaves in human volunteers.
2002 Jan-Mar
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.
2002 Jun
Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
2003 Jul
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 human urine and plasma by liquid chromatography/tandem mass spectrometry: collaborative study.
2003 Jul-Aug
Concentrations of ephedra alkaloids and caffeine in commercial dietary supplements.
2004 Apr
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
One internal standard for multiple analytes: a limit and solution.
2004 Sep-Oct
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
Doping control analysis in human urine by liquid chromatography-electrospray ionization ion trap mass spectrometry for the Olympic Games Athens 2004: determination of corticosteroids and quantification of ephedrines, salbutamol and morphine.
2006 Jul 28
The consumption of khat and other drugs in Somali combatants: a cross-sectional study.
2007 Dec
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
Simultaneous chiral separation of ephedrine alkaloids by MEKC-ESI-MS using polymeric surfactant II: application in dietary supplements.
2007 May
Results of stability studies with doping agents in urine.
2007 Nov-Dec
Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006.
2008 Jul
Illicit cathinone ("Hagigat") poisoning.
2008 Mar
Urinary elimination of ephedrines following administration of the Traditional Chinese Medicine preparation Kakkon-to.
2008 Nov-Dec
Miscellaneous.
2008 Oct
Khat - a controversial plant.
2009
Elimination of ephedrines in urine following administration of a Sho-seiryu-to preparation.
2009 Apr
Problems of the use of pseudoephedrine by athletes.
2009 Aug
Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis.
2009 Dec 5
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
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
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
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
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
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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
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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