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Details

Stereochemistry ABSOLUTE
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

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
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
Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule.
2003 May 1
In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates.
2003 Oct
Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat.
2004 Jun
Khat (Catha edulis)-induced apoptosis is inhibited by antagonists of caspase-1 and -8 in human leukaemia cells.
2004 Nov 1
One internal standard for multiple analytes: a limit and solution.
2004 Sep-Oct
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
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.
2007 Feb
Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats.
2007 May
A review of the neuropharmacological properties of khat.
2008 Jul 1
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
Development and validation of an LC-MS/MS method for the quantification of ephedrines in urine.
2009 Feb 1
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 monitoring drug use in Europe: the current situation and issues for the future.
2010 Dec 1
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
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.
Name Type Language
CATHINE
INN   MART.   WHO-DD  
INN  
Official Name English
CATHINUM
Common Name English
NORPSEUDOEPHEDRINE [MI]
Common Name English
Cathine [WHO-DD]
Common Name English
(1S,2S)-PSEUDONOREPHEDRINE
Common Name English
NORPSEUDOEPHEDRINE, D-
Common Name English
cathine [INN]
Common Name English
(1S,2S)-(+)-NORPSEUDOEPHEDRINE
Common Name English
PHENYLPROPANOLAMINE D-THREO-FORM [MI]
Common Name English
THREO-2-AMINO-1-PHENYLPROPAN-1-OL
Common Name English
BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-, (.ALPHA.S)-
Common Name English
CATINA
Common Name English
(1S,2S)-2-AMINO-1-PHENYL-1-PROPANOL
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, (S-(R*,R*))-
Common Name English
(+)-NORPSEUDOEPHEDRINE
Common Name English
D-(+)-NORPSEUDOEPHEDRINE
Common Name English
CATHINE [MART.]
Common Name English
(1S,2S)-2-AMINO-1-PHENYLPROPAN-1-OL
Common Name English
Classification Tree Code System Code
WHO-VATC QA08AA07
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
NCI_THESAURUS C221
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
WHO-ATC A08AA07
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
DEA NO. 1230
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
Code System Code Type Description
RXCUI
32022
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID50889347
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PRIMARY
DRUG CENTRAL
3389
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PRIMARY
WIKIPEDIA
CATHINE
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
PUBCHEM
441457
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PRIMARY
MERCK INDEX
m8073
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PRIMARY Merck Index
NCI_THESAURUS
C79914
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PRIMARY
CAS
492-39-7
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PRIMARY
ChEMBL
CHEMBL1412041
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PRIMARY
FDA UNII
E1L4ZW2F8O
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PRIMARY
DRUG BANK
DB01486
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PRIMARY
MESH
C005331
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
SMS_ID
100000081373
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
MERCK INDEX
m8687
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY Merck Index
INN
4952
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-754-1
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY
EVMPD
SUB06158MIG
Created by admin on Fri Dec 15 17:40:21 GMT 2023 , Edited by admin on Fri Dec 15 17:40:21 GMT 2023
PRIMARY