CATHINE HYDROCHLORIDE

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 Search

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

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20553832
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
norepinephrine secretion 9 Target ID: GO:0048243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796	Activator 1447
dopamine secretion 11 Target ID: GO:0014046 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 206 Sources: http://www.medicalook.com/reviews/Norpseudoephedrin.html	Primary		Approved 8583	CATHINE HYDROCHLORIDE Approved Use Treatment of obesity

C_max

Value	Dose	Co-administered	Analyte	Population
71.2 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12848785/	0.498 g/kg single, oral dose: 0.498 g/kg route of administration: Oral experiment type: SINGLE co-administered:		CATHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
713 μg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12848785/	0.498 g/kg single, oral dose: 0.498 g/kg route of administration: Oral experiment type: SINGLE co-administered:		CATHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12848785/	0.498 g/kg single, oral dose: 0.498 g/kg route of administration: Oral experiment type: SINGLE co-administered:		CATHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
87.5 mg 1 times / day multiple, oral Highest recorded dose Dose: 87.5 mg, 1 times / day Route: oral Route: multiple Dose: 87.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/	Disc. AE: Psychosis, Drug dependence... AEs leading to discontinuation/dose reduction: Psychosis Drug dependence Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/
30 mg 2 times / week multiple, oral Recommended Dose: 30 mg, 2 times / week Route: oral Route: multiple Dose: 30 mg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8164019/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8164019/	Disc. AE: Dyskinesia... AEs leading to discontinuation/dose reduction: Dyskinesia Sources: https://pubmed.ncbi.nlm.nih.gov/8164019/
49 mg 1 times / day multiple, oral Recommended Dose: 49 mg, 1 times / day Route: oral Route: multiple Dose: 49 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9775158/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9775158/	Other AEs: ubarachnoid hemorrhage... Other AEs: ubarachnoid hemorrhage Sources: https://pubmed.ncbi.nlm.nih.gov/9775158/
53.3 mg 1 times / day multiple, oral Studied dose Dose: 53.3 mg, 1 times / day Route: oral Route: multiple Dose: 53.3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/	Disc. AE: Dry mouth, ry mouth... AEs leading to discontinuation/dose reduction: Dry mouth (3.3%) ry mouth (3.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/

AEs

AE	Significance	Dose	Population
Drug dependence	Disc. AE	87.5 mg 1 times / day multiple, oral Highest recorded dose Dose: 87.5 mg, 1 times / day Route: oral Route: multiple Dose: 87.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/
Psychosis	Disc. AE	87.5 mg 1 times / day multiple, oral Highest recorded dose Dose: 87.5 mg, 1 times / day Route: oral Route: multiple Dose: 87.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14680722/
Dyskinesia	Disc. AE	30 mg 2 times / week multiple, oral Recommended Dose: 30 mg, 2 times / week Route: oral Route: multiple Dose: 30 mg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8164019/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8164019/
ubarachnoid hemorrhage		49 mg 1 times / day multiple, oral Recommended Dose: 49 mg, 1 times / day Route: oral Route: multiple Dose: 49 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9775158/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9775158/
Dry mouth	3.3% Disc. AE	53.3 mg 1 times / day multiple, oral Studied dose Dose: 53.3 mg, 1 times / day Route: oral Route: multiple Dose: 53.3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/
ry mouth	3.3% Disc. AE	53.3 mg 1 times / day multiple, oral Studied dose Dose: 53.3 mg, 1 times / day Route: oral Route: multiple Dose: 53.3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28873376/

PubMed

Title	Date	PubMed
Khat use and neurobehavioral functions: suggestions for future studies.	2010-12-01	20553832
Khat use and monitoring drug use in Europe: the current situation and issues for the future.	2010-12-01	20452413
Motives for khat use and abstinence in Yemen--a gender perspective.	2010-11-27	21110889
Fast analysis of doping agents in urine by ultra-high-pressure liquid chromatography-quadrupole time-of-flight mass spectrometry. II: Confirmatory analysis.	2010-06-18	19939397
Analysis of stimulants in oral fluid and urine by gas chromatography-mass spectrometry II: pseudophedrine.	2010-05	20465867
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.	2010-02-25	20047807
Cathinone preservation in khat evidence via drying.	2010-02-25	20036789
Influence of triiodothyronine on the contractile effect of D-nor-pseudoephedrine.	2010	22128448
Long-term effects of chronic khat use: impaired inhibitory control.	2010	21833274
Influence of Khat Chewing on Periodontal Tissues and Oral Hygiene Status among Yemenis.	2010	21448439
Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis.	2009-12-05	19574012
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.	2009-11-13	19912650
Time for a "Third Wave" of malaria activism to tackle the drug stock-out crisis.	2009-11	19936043
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.	2009-08-23	19698178
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.	2009-08	19571776
Problems of the use of pseudoephedrine by athletes.	2009-08	19382058
Keep an eye on the pupil: developing countries under chemical attack.	2009-06	19367469
Interpretation of urinary concentrations of pseudoephedrine and its metabolite cathine in relation to doping control.	2009-05	20355197
Elimination of ephedrines in urine following administration of a Sho-seiryu-to preparation.	2009-04	19371465
Extraction and microencapsulation of khat: effects on sexual motivation and estradiol level in female rats.	2009-03	19143913
The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.	2009-02-17	19154154
Development and validation of an LC-MS/MS method for the quantification of ephedrines in urine.	2009-02-01	19144576
Qualitative confirmation procedure for ephedrines as acetonide derivatives in doping urine samples by gas chromatography/electron ionization mass spectrometry.	2009-01	19072865
Khat - a controversial plant.	2009	19921126
Risk assessment of khat use in the Netherlands: a review based on adverse health effects, prevalence, criminal involvement and public order.	2008-12	18783727
Urinary elimination of ephedrines following administration of the Traditional Chinese Medicine preparation Kakkon-to.	2008-11-22	19021932
Miscellaneous.	2008-10	21593974
A review of the neuropharmacological properties of khat.	2008-07-01	18561890
Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006.	2008-07	18558039
Illicit cathinone ("Hagigat") poisoning.	2008-03	17852166
Results of stability studies with doping agents in urine.	2007-12-21	18093412
Developmental patterns of phenylpropylamino alkaloids accumulation in khat (Catha edulis, Forsk.).	2007-12-03	17928181
The consumption of khat and other drugs in Somali combatants: a cross-sectional study.	2007-12	18076280
Effect of Catha edulis (khat) on behaviour and its potential to induce seizures in Sprague Dawley rats.	2007-05	17892196
Simultaneous chiral separation of ephedrine alkaloids by MEKC-ESI-MS using polymeric surfactant II: application in dietary supplements.	2007-05	17465418
[Khat--a new drug of abuse in Norway].	2007-03-01	17332809
Cathine, an amphetamine-related compound, acts on mammalian spermatozoa via beta1- and alpha2A-adrenergic receptors in a capacitation state-dependent manner.	2007-03	17158213
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.	2007-02	17154352
The subjective effects of chewing Qat leaves in human volunteers.	2007-01-30	17259764
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	17523214
Stability studies of amphetamine and ephedrine derivatives in urine.	2006-10-20	16798115
A rapid and simple procedure for the determination of ephedrine alkaloids in dietary supplements by gas chromatography-mass spectrometry.	2006-08-28	16580167
Doping control analysis in human urine by liquid chromatography-electrospray ionization ion trap mass spectrometry for the Olympic Games Athens 2004: determination of corticosteroids and quantification of ephedrines, salbutamol and morphine.	2006-07-28	17723530
Metabolites of ephedrines in human urine after administration of a single therapeutic dose.	2006-03-10	15885945
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.	2005-10-15	16154527
Simultaneous quantification of six ephedrines in a Mahwang preparation and in urine by high-performance liquid chromatography.	2005-06	15931652
Khat use as risk factor for psychotic disorders: a cross-sectional and case-control study in Somalia.	2005-02-12	15707502
Cathine and norephedrine, both phenylpropanolamines, accelerate capacitation and then inhibit spontaneous acrosome loss.	2005-01	15513978
Investigation of the silylation of ephedrines using N-methyl-N-trimethylsilyl-trifluoroacetamide.	2004-11-25	15522721
One internal standard for multiple analytes: a limit and solution.	2004-10-21	15493661

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 19:27:01 GMT 2025` Edited by `admin` on `Mon Mar 31 19:27:01 GMT 2025`
Record UNII	IX73851J3P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORPSEUDOEPHEDRINE HYDROCHLORIDE

Preferred Name

English

CATHINE HYDROCHLORIDE

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

Cathine hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

218-446-1