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 |
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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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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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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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Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat. | 2004 Jun |
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Khat (Catha edulis)-induced apoptosis is inhibited by antagonists of caspase-1 and -8 in human leukaemia cells. | 2004 Nov 1 |
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One internal standard for multiple analytes: a limit and solution. | 2004 Sep-Oct |
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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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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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Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats. | 2007 May |
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A review of the neuropharmacological properties of khat. | 2008 Jul 1 |
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Khat - a controversial plant. | 2009 |
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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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Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic. | 2009 Aug 23 |
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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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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 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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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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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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207-754-1
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SUB06158MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)