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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO.ClH
Molecular Weight 187.667
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CATHINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=DYWNLSQWJMTVGJ-DKXTVVGFSA-N
InChI=1S/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Investigation of the silylation of ephedrines using N-methyl-N-trimethylsilyl-trifluoroacetamide.
2004 Nov 25
One internal standard for multiple analytes: a limit and solution.
2004 Sep-Oct
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
A rapid and simple procedure for the determination of ephedrine alkaloids in dietary supplements by gas chromatography-mass spectrometry.
2006 Aug 28
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
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
[Khat--a new drug of abuse in Norway].
2007 Mar 1
Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats.
2007 May
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
Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order.
2008 Dec
Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006.
2008 Jul
A review of the neuropharmacological properties of khat.
2008 Jul 1
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:55:59 UTC 2023
Edited
by admin
on Fri Dec 15 18:55:59 UTC 2023
Record UNII
IX73851J3P
Record Status Validated (UNII)
Record Version
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Name Type Language
CATHINE HYDROCHLORIDE
WHO-DD  
Common Name English
FASUPOND
Brand Name English
AMORPHAN
Brand Name English
NORPSEUDOEPHEDRINE HYDROCHLORIDE [MI]
Common Name English
BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-, HYDROCHLORIDE (1:1), (.ALPHA.S)-
Common Name English
MINUSIN
Brand Name English
CATHINE HCL
Common Name English
(+)-NORPSEUDOEPHEDRINE HYDROCHLORIDE
Common Name English
NORPSEUDOEPHEDRINE HYDROCHLORIDE
MI  
Common Name English
Cathine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
218-446-1
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID70891149
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
CAS
2153-98-2
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
MERCK INDEX
m8073
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY Merck Index
FDA UNII
IX73851J3P
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
EVMPD
SUB01089MIG
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
RXCUI
236860
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY RxNorm
PUBCHEM
92920
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
SMS_ID
100000084878
Created by admin on Fri Dec 15 18:55:59 UTC 2023 , Edited by admin on Fri Dec 15 18:55:59 UTC 2023
PRIMARY
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