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

Details

Stereochemistry RACEMIC
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

Molecular Formula C9H13NO
Molecular Weight 151.2056
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
2002 Oct
Investigation of quality in ephedrine-containing dietary supplements.
2003
Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
2003 Jul
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
Determination of ephedra alkaloid and caffeine concentrations in dietary supplements and biological fluids.
2004 Apr
Analysis of ephedra-alkaloids using sweeping and cation-selective exhaustive injection and sweeping micellar electrokinetic chromatography methods.
2004 Feb
Reference materials for analytical toxicology including doping control: freeze-dried urine samples.
2004 May
Khat (Catha edulis)-induced apoptosis is inhibited by antagonists of caspase-1 and -8 in human leukaemia cells.
2004 Nov 1
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
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
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
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
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
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:00:35 GMT 2023
Edited
by admin
on Sat Dec 16 09:00:35 GMT 2023
Record UNII
27A0HLC3HH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CATHINE, (±)-
Common Name English
BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, (.ALPHA.R)-REL-
Systematic Name English
(±)-NORPSEUDOEPHEDRINE
Common Name English
EXPONCIT
Brand Name English
MINUSINE
Brand Name English
PSEUDONOREPHEDRINE
Common Name English
THREO-2-AMINO-1-HYDROXY-1-PHENYLPROPANE
Common Name English
THREO-1-PHENYL-1-HYDROXY-2-AMINOPROPANE
Common Name English
.OMEGA.-NOREPHEDRINE
Common Name English
NORPSEUDOEPHEDRINE
Common Name English
RACEMIC NORPSEUDOEPHEDRINE
Common Name English
Classification Tree Code System Code
DEA NO. 8317
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
Code System Code Type Description
FDA UNII
27A0HLC3HH
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID20889399
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
PUBCHEM
441457
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
CAS
36393-56-3
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
253-014-6
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE
Norpseudoephedrine is a major metabolite of diethylpropion in man under acidic urine conditions.
PARENT -> METABOLITE