Details
Stereochemistry | RACEMIC |
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
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 |
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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Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers. | 2003 Apr 23 |
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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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Determination of ephedrine alkaloids in human urine and plasma by liquid chromatography/tandem mass spectrometry: collaborative study. | 2003 Jul-Aug |
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Determination of ephedra alkaloid and caffeine concentrations in dietary supplements and biological fluids. | 2004 Apr |
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Concentrations of ephedra alkaloids and caffeine in commercial dietary supplements. | 2004 Apr |
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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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Driving under the influence of khat--alkaloid concentrations and observations in forensic cases. | 2004 Feb 10 |
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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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Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia. | 2005 Feb 12 |
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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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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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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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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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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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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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Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine. | 2010 May |
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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
Sat Dec 16 09:00:35 GMT 2023
by
admin
on
Sat Dec 16 09:00:35 GMT 2023
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Record UNII |
27A0HLC3HH
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Record Status |
Validated (UNII)
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Record Version |
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DEA NO. |
8317
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27A0HLC3HH
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DTXSID20889399
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36393-56-3
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253-014-6
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
Norpseudoephedrine is a major metabolite of diethylpropion in man under acidic urine conditions.
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PARENT -> METABOLITE |
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