Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13NO.ClH |
Molecular Weight | 187.667 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C[C@H](N)[C@@H](O)C1=CC=CC=C1
InChI
InChIKey=DYWNLSQWJMTVGJ-DKXTVVGFSA-N
InChI=1S/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H/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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Synthesis of enantiopure homoallylic ethers by reagent controlled facial selective allylation of chiral ketones. | 2001 Jan 5 |
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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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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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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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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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Investigation of the silylation of ephedrines using N-methyl-N-trimethylsilyl-trifluoroacetamide. | 2004 Nov 25 |
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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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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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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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Metabolites of ephedrines in human urine after administration of a single therapeutic dose. | 2006 Mar 10 |
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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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Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis. | 2009 Dec 5 |
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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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Long-term effects of chronic khat use: impaired inhibitory control. | 2010 |
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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2153-98-2
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m8073
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IX73851J3P
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SUB01089MIG
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236860
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92920
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100000084878
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ACTIVE MOIETY
SUBSTANCE RECORD