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 |
---|---|---|---|
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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Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes. | 2001 Sep 5 |
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Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers. | 2003 Apr 23 |
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Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves. | 2003 Jul |
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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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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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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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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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Time for a "Third Wave" of malaria activism to tackle the drug stock-out crisis. | 2009 Nov |
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Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine. | 2010 May |
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 UTC 2023
by
admin
on
Sat Dec 16 09:00:35 UTC 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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-
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DEA NO. |
8317
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27A0HLC3HH
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DTXSID20889399
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441457
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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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