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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20553832Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20553832
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0048243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 |
|||
Target ID: GO:0014046 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CATHINE HYDROCHLORIDE Approved UseTreatment of obesity |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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One internal standard for multiple analytes: a limit and solution. | 2004 Sep-Oct |
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Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia. | 2005 Feb 12 |
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Cathine and norephedrine, both phenylpropanolamines, accelerate capacitation and then inhibit spontaneous acrosome loss. | 2005 Jan |
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Simultaneous quantification of six ephedrines in a Mahwang preparation and in urine by high-performance liquid chromatography. | 2005 Jun |
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Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches. | 2005 Oct 15 |
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A rapid and simple procedure for the determination of ephedrine alkaloids in dietary supplements by gas chromatography-mass spectrometry. | 2006 Aug 28 |
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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 |
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Metabolites of ephedrines in human urine after administration of a single therapeutic dose. | 2006 Mar 10 |
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Stability studies of amphetamine and ephedrine derivatives in urine. | 2006 Oct 20 |
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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 |
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The consumption of khat and other drugs in Somali combatants: a cross-sectional study. | 2007 Dec |
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Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.). | 2007 Dec 3 |
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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 |
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Simultaneous chiral separation of ephedrine alkaloids by MEKC-ESI-MS using polymeric surfactant II: application in dietary supplements. | 2007 May |
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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 |
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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 |
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Elimination of ephedrines in urine following administration of a Sho-seiryu-to preparation. | 2009 Apr |
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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 |
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Problems of the use of pseudoephedrine by athletes. | 2009 Aug |
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Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic. | 2009 Aug 23 |
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Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis. | 2009 Dec 5 |
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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 |
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Qualitative confirmation procedure for ephedrines as acetonide derivatives in doping urine samples by gas chromatography/electron ionization mass spectrometry. | 2009 Jan |
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Keep an eye on the pupil: developing countries under chemical attack. | 2009 Jun |
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Extraction and microencapsulation of khat: effects on sexual motivation and estradiol level in female rats. | 2009 Mar |
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Interpretation of urinary concentrations of pseudoephedrine and its metabolite cathine in relation to doping control. | 2009 May |
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Time for a "Third Wave" of malaria activism to tackle the drug stock-out crisis. | 2009 Nov |
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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 |
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Influence of triiodothyronine on the contractile effect of D-nor-pseudoephedrine. | 2010 |
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Long-term effects of chronic khat use: impaired inhibitory control. | 2010 |
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Khat use and neurobehavioral functions: suggestions for future studies. | 2010 Dec 1 |
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Khat use and monitoring drug use in Europe: the current situation and issues for the future. | 2010 Dec 1 |
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Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010 Feb 25 |
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Cathinone preservation in khat evidence via drying. | 2010 Feb 25 |
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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 |
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Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine. | 2010 May |
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Motives for khat use and abstinence in Yemen--a gender perspective. | 2010 Nov 27 |
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Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis. | 2010 Winter |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796
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
Edited
Fri Dec 15 18:55:59 UTC 2023
by
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on
Fri Dec 15 18:55:59 UTC 2023
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Record UNII |
IX73851J3P
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Record Status |
Validated (UNII)
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Record Version |
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2153-98-2
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100000084878
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