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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Synthesis of enantiopure homoallylic ethers by reagent controlled facial selective allylation of chiral ketones. | 2001 Jan 5 |
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Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry. | 2001 Sep |
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Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes. | 2001 Sep 5 |
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Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002 Jun |
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Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing. | 2002 Oct |
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Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers. | 2003 Apr 23 |
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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 dietary supplements and botanicals by liquid chromatography/tandem mass spectrometry: collaborative study. | 2003 Jul-Aug |
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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 |
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Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule. | 2003 May 1 |
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In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. | 2003 Oct |
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Analysis of ephedra-alkaloids using sweeping and cation-selective exhaustive injection and sweeping micellar electrokinetic chromatography methods. | 2004 Feb |
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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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Common drugs of abuse--Part II. | 2004 Spring |
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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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Stability studies of amphetamine and ephedrine derivatives in urine. | 2006 Oct 20 |
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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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[Khat--a new drug of abuse in Norway]. | 2007 Mar 1 |
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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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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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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 |
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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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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.
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Classification Tree | Code System | Code | ||
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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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492-39-7
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DB01486
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C005331
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m8687
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4952
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207-754-1
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SUB06158MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)