CATHINE, (±)-

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 Search

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
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
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.	2002 Jun	12087345
In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates.	2003 Oct	12954796
One internal standard for multiple analytes: a limit and solution.	2004 Sep-Oct	15493661
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.	2005 Oct 15	16154527
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.	2007 Feb	17154352
[Khat--a new drug of abuse in Norway].	2007 Mar 1	17332809
Results of stability studies with doping agents in urine.	2007 Nov-Dec	18093412
Association of smoking and khat (Catha edulis Forsk) use with high blood pressure among adults in Addis Ababa, Ethiopia, 2006.	2008 Jul	18558039
Population based prevalence of high blood pressure among adults in Addis Ababa: uncovering a silent epidemic.	2009 Aug 23	19698178
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	19912650
Influence of triiodothyronine on the contractile effect of D-nor-pseudoephedrine.	2010	22128448

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 22:26:09 GMT 2025` Edited by `admin` on `Mon Mar 31 22:26:09 GMT 2025`
Record UNII	27A0HLC3HH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EXPONCIT

Preferred Name

English

CATHINE, (±)-

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, (.ALPHA.R)-REL-

Systematic Name

English

(±)-NORPSEUDOEPHEDRINE

Common 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