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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
Structure of CATHINE HYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CATHINE HYDROCHLORIDE

Approved Use

Treatment of obesity
PubMed

PubMed

TitleDatePubMed
Synthesis of enantiopure homoallylic ethers by reagent controlled facial selective allylation of chiral ketones.
2001 Jan 5
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
2002 Oct
Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers.
2003 Apr 23
Determination of ephedrine alkaloids in dietary supplements and botanicals by liquid chromatography/tandem mass spectrometry: collaborative study.
2003 Jul-Aug
Determination of ephedrine alkaloids in human urine and plasma by liquid chromatography/tandem mass spectrometry: collaborative study.
2003 Jul-Aug
In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates.
2003 Oct
Concentrations of ephedra alkaloids and caffeine in commercial dietary supplements.
2004 Apr
Analysis of ephedra-alkaloids using sweeping and cation-selective exhaustive injection and sweeping micellar electrokinetic chromatography methods.
2004 Feb
Driving under the influence of khat--alkaloid concentrations and observations in forensic cases.
2004 Feb 10
Determination of ephedra alkaloids in urine and plasma by HPLC-UV: collaborative study.
2004 Jan-Feb
Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat.
2004 Jun
Investigation of the silylation of ephedrines using N-methyl-N-trimethylsilyl-trifluoroacetamide.
2004 Nov 25
Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia.
2005 Feb 12
Cathine and norephedrine, both phenylpropanolamines, accelerate capacitation and then inhibit spontaneous acrosome loss.
2005 Jan
Simultaneous quantification of six ephedrines in a Mahwang preparation and in urine by high-performance liquid chromatography.
2005 Jun
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
A rapid and simple procedure for the determination of ephedrine alkaloids in dietary supplements by gas chromatography-mass spectrometry.
2006 Aug 28
Metabolites of ephedrines in human urine after administration of a single therapeutic dose.
2006 Mar 10
Cathine, an amphetamine-related compound, acts on mammalian spermatozoa via beta1- and alpha2A-adrenergic receptors in a capacitation state-dependent manner.
2007 Mar
[Khat--a new drug of abuse in Norway].
2007 Mar 1
Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis.
2009 Dec 5
Qualitative confirmation procedure for ephedrines as acetonide derivatives in doping urine samples by gas chromatography/electron ionization mass spectrometry.
2009 Jan
Keep an eye on the pupil: developing countries under chemical attack.
2009 Jun
Extraction and microencapsulation of khat: effects on sexual motivation and estradiol level in female rats.
2009 Mar
Interpretation of urinary concentrations of pseudoephedrine and its metabolite cathine in relation to doping control.
2009 May
Long-term effects of chronic khat use: impaired inhibitory control.
2010
Patents

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
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.
Name Type Language
CATHINE HYDROCHLORIDE
WHO-DD  
Common Name English
FASUPOND
Brand Name English
AMORPHAN
Brand Name English
NORPSEUDOEPHEDRINE HYDROCHLORIDE [MI]
Common Name English
BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-, HYDROCHLORIDE (1:1), (.ALPHA.S)-
Common Name English
MINUSIN
Brand Name English
CATHINE HCL
Common Name English
(+)-NORPSEUDOEPHEDRINE HYDROCHLORIDE
Common Name English
NORPSEUDOEPHEDRINE HYDROCHLORIDE
MI  
Common Name English
Cathine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
218-446-1
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID70891149
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY
CAS
2153-98-2
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY
MERCK INDEX
m8073
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY Merck Index
FDA UNII
IX73851J3P
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY
EVMPD
SUB01089MIG
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY
RXCUI
236860
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY RxNorm
PUBCHEM
92920
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY
SMS_ID
100000084878
Created by admin on Fri Dec 15 18:55:59 GMT 2023 , Edited by admin on Fri Dec 15 18:55:59 GMT 2023
PRIMARY