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
Investigation of quality in ephedrine-containing dietary supplements.
2003
Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers.
2003 Apr 23
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
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
Determination of ephedra alkaloid and caffeine concentrations in dietary supplements and biological fluids.
2004 Apr
Determination of ephedra alkaloids in urine and plasma by HPLC-UV: collaborative study.
2004 Jan-Feb
One internal standard for multiple analytes: a limit and solution.
2004 Sep-Oct
Common drugs of abuse--Part II.
2004 Spring
Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia.
2005 Feb 12
Cathine and norephedrine, both phenylpropanolamines, accelerate capacitation and then inhibit spontaneous acrosome loss.
2005 Jan
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
Metabolites of ephedrines in human urine after administration of a single therapeutic dose.
2006 Mar 10
Stability studies of amphetamine and ephedrine derivatives in urine.
2006 Oct 20
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
The consumption of khat and other drugs in Somali combatants: a cross-sectional study.
2007 Dec
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).
2007 Dec 3
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
Results of stability studies with doping agents in urine.
2007 Nov-Dec
Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order.
2008 Dec
A review of the neuropharmacological properties of khat.
2008 Jul 1
Miscellaneous.
2008 Oct
Elimination of ephedrines in urine following administration of a Sho-seiryu-to preparation.
2009 Apr
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
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
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
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
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
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
FDA UNII
E1L4ZW2F8O
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 BANK
DB01486
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
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