U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CATHINE, (±)-

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

HIDE SMILES / InChI

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

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
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
Determination of ephedra alkaloid and caffeine concentrations in dietary supplements and biological fluids.
2004 Apr
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
Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia.
2005 Feb 12
Metabolites of ephedrines in human urine after administration of a single therapeutic dose.
2006 Mar 10
Stability studies of amphetamine and ephedrine derivatives in urine.
2006 Oct 20
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
The consumption of khat and other drugs in Somali combatants: a cross-sectional study.
2007 Dec
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).
2007 Dec 3
Cathine, an amphetamine-related compound, acts on mammalian spermatozoa via beta1- and alpha2A-adrenergic receptors in a capacitation state-dependent manner.
2007 Mar
Illicit cathinone ("Hagigat") poisoning.
2008 Mar
Urinary elimination of ephedrines following administration of the Traditional Chinese Medicine preparation Kakkon-to.
2008 Nov-Dec
Khat - a controversial plant.
2009
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
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.
2009 Aug 23
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
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
Influence of triiodothyronine on the contractile effect of D-nor-pseudoephedrine.
2010
Long-term effects of chronic khat use: impaired inhibitory control.
2010
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine.
2010 May
Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis.
2010 Winter
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:00:35 GMT 2023
Edited
by admin
on Sat Dec 16 09:00:35 GMT 2023
Record UNII
27A0HLC3HH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CATHINE, (±)-
Common Name English
BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, (.ALPHA.R)-REL-
Systematic Name English
(±)-NORPSEUDOEPHEDRINE
Common Name English
EXPONCIT
Brand Name English
MINUSINE
Brand Name English
PSEUDONOREPHEDRINE
Common Name English
THREO-2-AMINO-1-HYDROXY-1-PHENYLPROPANE
Common Name English
THREO-1-PHENYL-1-HYDROXY-2-AMINOPROPANE
Common Name English
.OMEGA.-NOREPHEDRINE
Common Name English
NORPSEUDOEPHEDRINE
Common Name English
RACEMIC NORPSEUDOEPHEDRINE
Common Name English
Classification Tree Code System Code
DEA NO. 8317
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
Code System Code Type Description
FDA UNII
27A0HLC3HH
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID20889399
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
PUBCHEM
441457
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
CAS
36393-56-3
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
253-014-6
Created by admin on Sat Dec 16 09:00:35 GMT 2023 , Edited by admin on Sat Dec 16 09:00:35 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE
Norpseudoephedrine is a major metabolite of diethylpropion in man under acidic urine conditions.
PARENT -> METABOLITE