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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
Synthesis of enantiopure homoallylic ethers by reagent controlled facial selective allylation of chiral ketones.
2001 Jan 5
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.
2001 Sep 5
Determination of cathinone, cathine and norephedrine in hair of Yemenite khat chewers.
2003 Apr 23
Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
2003 Jul
Investigation of the silylation of ephedrines using N-methyl-N-trimethylsilyl-trifluoroacetamide.
2004 Nov 25
One internal standard for multiple analytes: a limit and solution.
2004 Sep-Oct
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
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
Development and validation of an LC-MS/MS method for the quantification of ephedrines in urine.
2009 Feb 1
The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.
2009 Feb 17
Qualitative confirmation procedure for ephedrines as acetonide derivatives in doping urine samples by gas chromatography/electron ionization mass spectrometry.
2009 Jan
Time for a "Third Wave" of malaria activism to tackle the drug stock-out crisis.
2009 Nov
Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine.
2010 May
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 UTC 2023
Edited
by admin
on Sat Dec 16 09:00:35 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 09:00:35 UTC 2023
Code System Code Type Description
FDA UNII
27A0HLC3HH
Created by admin on Sat Dec 16 09:00:35 UTC 2023 , Edited by admin on Sat Dec 16 09:00:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID20889399
Created by admin on Sat Dec 16 09:00:35 UTC 2023 , Edited by admin on Sat Dec 16 09:00:35 UTC 2023
PRIMARY
PUBCHEM
441457
Created by admin on Sat Dec 16 09:00:35 UTC 2023 , Edited by admin on Sat Dec 16 09:00:35 UTC 2023
PRIMARY
CAS
36393-56-3
Created by admin on Sat Dec 16 09:00:35 UTC 2023 , Edited by admin on Sat Dec 16 09:00:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
253-014-6
Created by admin on Sat Dec 16 09:00:35 UTC 2023 , Edited by admin on Sat Dec 16 09:00:35 UTC 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