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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
The subjective effects of chewing Qat leaves in human volunteers.
2002 Jan-Mar
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.
2002 Jun
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
Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves.
2003 Jul
Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction.
2003 Jul 5
Determination of ephedrine alkaloids in dietary supplements and botanicals 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
Determination of ephedra alkaloids in urine and plasma by HPLC-UV: collaborative study.
2004 Jan-Feb
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
[Khat--a new drug of abuse in Norway].
2007 Mar 1
A review of the neuropharmacological properties of khat.
2008 Jul 1
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.
2009 Aug 23
Development and validation of an LC-MS/MS method for the quantification of ephedrines in urine.
2009 Feb 1
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
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
Cathinone preservation in khat evidence via drying.
2010 Feb 25
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