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
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
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 |
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Target ID: GO:0014046 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | CATHINE HYDROCHLORIDE Approved UseTreatment of obesity |
PubMed
Title | Date | PubMed |
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The subjective effects of chewing Qat leaves in human volunteers. | 2002 Jan-Mar |
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Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002 Jun |
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Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves. | 2003 Jul |
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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 |
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Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction. | 2003 Jul 5 |
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Determination of ephedrine alkaloids in human urine and plasma by liquid chromatography/tandem mass spectrometry: collaborative study. | 2003 Jul-Aug |
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Concentrations of ephedra alkaloids and caffeine in commercial dietary supplements. | 2004 Apr |
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Determination of ephedra alkaloids in urine and plasma by HPLC-UV: collaborative study. | 2004 Jan-Feb |
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Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat. | 2004 Jun |
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One internal standard for multiple analytes: a limit and solution. | 2004 Sep-Oct |
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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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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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The consumption of khat and other drugs in Somali combatants: a cross-sectional study. | 2007 Dec |
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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 |
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Cathine, an amphetamine-related compound, acts on mammalian spermatozoa via beta1- and alpha2A-adrenergic receptors in a capacitation state-dependent manner. | 2007 Mar |
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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 |
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Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006. | 2008 Jul |
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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 |
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Miscellaneous. | 2008 Oct |
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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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Problems of the use of pseudoephedrine by athletes. | 2009 Aug |
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Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis. | 2009 Dec 5 |
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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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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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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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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 |
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.
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WHO-VATC |
QA08AA07
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NCI_THESAURUS |
C221
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WHO-ATC |
A08AA07
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DEA NO. |
1230
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32022
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DTXSID50889347
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3389
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CATHINE
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441457
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m8073
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C79914
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DB01486
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C005331
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207-754-1
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SUB06158MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)