PSEUDOEPHEDRINE

US Approved OTC

First approved in 1961

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO
Molecular Weight	165.2322
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@@H](C)[C@@H](O)C1=CC=CC=C1

InChI

InChIKey=KWGRBVOPPLSCSI-WCBMZHEXSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H15NO
Molecular Weight	165.2322
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/pseudoephedrine.html
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12373557 | http://www.mayoclinic.org/drugs-supplements/ephedra--ma-huang/background/hrb-20059270 | https://www.sudafed.com/adult-products/congestion/sudafed-24-hour#uses-and-directions | https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0011888 | https://www.ncbi.nlm.nih.gov/pubmed/11772135 | https://www.ncbi.nlm.nih.gov/pubmed/10449190 | https://www.ncbi.nlm.nih.gov/pubmed/12954796

Pseudoephedrine is a sympathomimetic drug. Pseudoephedrine acts as an adrenomimetic and inhibitor of monoamine transporters. Ephedra sinica, a species of ephedra (ma huang), contains ephedrine and pseudoephedrine. Ephedra has been found to stimulate the nervous system, increase airflow into the lungs and constrict blood vessels. In combination with caffeine, ephedra appears to cause weight loss. Pseudoephedrine is a decongestant that shrinks blood vessels in the nasal passages. Pseudoephedrine is used to relieve nasal or sinus congestion caused by the common cold, sinusitis, and hay fever and other respiratory allergies.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 179 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 8228	5.6 µM [IC50]
Norepinephrine transporter 190 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 8228	1.18 µM [IC50]
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796	Agonist 2662
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10449190	Agonist 2662

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nasal congestion 26 Sources: https://www.drugs.com/ppa/pseudoephedrine.html	Primary		Approved 8360	SUDAFED 24 HOUR Approved Use temporarily relieves nasal congestion due to the common cold, hay fever or other upper respiratory allergies; reduces swelling of nasal passages; relieves sinus pressure Launch Date 7.2429122E11

C_max

Value	Dose	Co-administered	Analyte	Population
292 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/073585Orig1s000.pdf	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		PSEUDOEPHEDRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
4346 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/073585Orig1s000.pdf	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		PSEUDOEPHEDRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.3 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/073585Orig1s000.pdf	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		PSEUDOEPHEDRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
1500 mg single, oral Overdose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19006543	unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/19006543	Other AEs: Rhabdomyolysis, Creatine kinase increased... Other AEs: Rhabdomyolysis (1 patient) Creatine kinase increased (1 patient) Blood myoglobin increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19006543
150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/729619	healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: https://pubmed.ncbi.nlm.nih.gov/729619	Other AEs: Tension, Dry mouth... Other AEs: Tension (10 patients) Dry mouth (6 patients) Tachycardia (9 patients) Palpitations (10 patients) Anxiety (13 patients) Insomnia (12 patients) Anorexia (7 patients) Restlessness (10 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/729619
90 mg 1 times / day multiple, oral Overdose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18365604	unhealthy, 3 years n = 1 Health Status: unhealthy Age Group: 3 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/18365604	Disc. AE: Urinary retention... AEs leading to discontinuation/dose reduction: Urinary retention (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18365604
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
720 mg 1 times / day multiple, oral Highest studied dose Dose: 720 mg, 1 times / day Route: oral Route: multiple Dose: 720 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23918202	unhealthy, 38.8 years n = 38 Health Status: unhealthy Age Group: 38.8 years Sex: M+F Population Size: 38 Sources: https://pubmed.ncbi.nlm.nih.gov/23918202	Sources: https://pubmed.ncbi.nlm.nih.gov/23918202
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis \| allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) chlorpheniramine maleate(2 mg; twice daily, oral) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
720 mg single, oral Overdose Dose: 720 mg Route: oral Route: single Dose: 720 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18608273	unhealthy, 87 years n = 1 Health Status: unhealthy Age Group: 87 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/18608273	Other AEs: Hypertension... Other AEs: Hypertension (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18608273

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51209	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51209
ZINC	ZINC000000020259	http://zinc15.docking.org/substances/ZINC000000020259
eMolecules	494893	https://www.emolecules.com/cgi-bin/more?vid=494893

PubMed

Title	Date	PubMed
A Double-blind crossover trial of pseudoephedrine and triprolidine, alone and in combination, for the treatment of allergenic rhinitis.	1975 Jan	1098524
Dextromethorphan- and pseudoephedrine-induced agitated psychosis and ataxia: case report.	1999 Mar-Apr	10195488
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Angle closure risk from proprietary medicines.	2001 Apr	11339612
Mass spectrometric quantitation of chiral drugs by the kinetic method.	2001 Apr 15	11338581
Study on the chiral recognition of the enantiomers of ephedrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-beta-cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry.	2001 Apr 20	11358226
Stereocontrolled Mannich reaction with enolizable imines using (S,S)-(+)-pseudoephedrine as chiral auxiliary. Asymmetric synthesis of alpha,beta-disubstituted beta-aminoesters and beta-lactams.	2001 Dec 28	11749640
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.	2001 Jan-Feb	11153535
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.	2001 Jun	11377047
Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines.	2001 Mar 8	11259059
[Cost effectiveness of GM-CSF in the treatment of acute myeloblastic leukemia in aged patients: protocol of GOELAM Sa3].	2001 Mar-Apr	11471363
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine.	2001 Mar-Apr	11345158
Factitious hypertension by pseudoephedrine.	2001 Mar-Apr	11239129
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.	2001 May	11361053
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid.	2001 May	11336106
Epinephrine analogues.	2001 Nov	12806441
Desloratadine reduces nasal congestion in patients with intermittent allergic rhinitis.	2001 Nov	11703222
Acute psychosis due to the interaction of legal compounds--ephedra alkaloids in 'vigueur fit' tablets, caffeine in 'red bull' and alcohol.	2001 Oct	11693229
Small-cell carcinoma of the esophagus: report of three cases and review of the literature with emphasis on therapy.	2001 Sep	11697847
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.	2001 Sep	11593992
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.	2001 Sep	11470203
Analysis of enantiomers giving partially overlapped peaks by using different treatments of the chromatographic ultraviolet signals: quantification of pseudoephedrine enantiomers.	2001 Sep 28	11681584
Myocardial infarction temporally related to ephedra--a possible role for the coronary microcirculation.	2002	12426924
Liquid chromatography/tandem mass spectrometric bioanalysis using normal-phase columns with aqueous/organic mobile phases - a novel approach of eliminating evaporation and reconstitution steps in 96-well SPE.	2002	12362389
Generalized dermatitis due to pseudoephedrine.	2002 Aug	12121199
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.	2002 Feb 15	11871684
Pseudoephedrine causing mania-like symptoms.	2002 Feb 22	11913943
Immediate hypersensitivity due to pseudoephedrine.	2002 Jan	11991291
Rapid determination of pseudoephedrine in human plasma by high-performance liquid chromatography.	2002 Jan 25	11824817
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.	2002 Jun	12087345
Implementation of the Comprehensive Methamphetamine Control Act of 1996; regulation of pseudoephedrine, phenylpropanolamine, and combination ephedrine drug products and reports of certain transactions to nonregulated persons. Final rule.	2002 Mar 28	11922057
[Blood supply of the lips].	2002 Oct	12449862
[Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients].	2002 Oct	12442126
Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers.	2002 Oct	12373557
[Toxic dermatitis caused by pseudoephedrine: apropos of a case].	2002 Sep	12389444
Baboon syndrome due to pseudoephedrine.	2003 Apr	12786741
Sensitive determination of ephedrine and pseudoephedrine by capillary electrophoresis with laser-induced fluorescence detection.	2003 Apr	12741643
Surfing, self-medicating and safety: buying non-prescription and complementary medicines via the internet.	2003 Apr	12679503
Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise.	2003 Jan	12582945
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.	2003 Jul	12791938
[Tobacco: knowledge, reasoning and opinion of high school students in Doubs. Reflections on prevention].	2003 Mar	12806810
Safety of selegiline with cold medications.	2003 Mar	12639177
Adrenaline given outside the context of life threatening allergic reactions.	2003 Mar 15	12637407
A comparative study of root canal preparation using FlexMaster and HERO 642 rotary Ni-Ti instruments.	2003 May	12752650
Canine model of nasal congestion and allergic rhinitis.	2003 May	12547842
Press-coating of immediate release powders onto coated controlled release tablets with adhesives.	2003 May 20	12737841

Patents

Sample Use Guides

In Vivo Use Guide

SUDAFED® 24 HOUR TABLET, EXTENDED RELEASE; ORAL (PSEUDOEPHEDRINE HYDROCHLORIDE) 240MG adults and children 12 years and older: a tablet with water every 24 hours children under 12 years: do not use this product in children under 12 years of age

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:52:18 UTC 2023` Edited by `admin` on `Wed Jul 05 22:52:18 UTC 2023`
Record UNII	7CUC9DDI9F
Record Status	`Validated (UNII)`
Record Version

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Related Record	Type

Name

Type

Language

PSEUDOEPHEDRINE

Official Name

English

(1S,2S)-(+)-PSEUDOEPHEDRINE

Common Name

English

(.ALPHA.S)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL

Systematic Name

English

(+)-(1S,2S)-PSEUDOEPHEDRINE

Common Name

English

PSEUDOEPHEDRINE [VANDF]

Common Name

English

EPHEDRINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

ACUNASO

Brand Name

English

1-(S),2-(R)-ERYTHRO-(+)-EPHEDRINE

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-

Systematic Name

English

pseudoephedrine [INN]

Common Name

English

PSEUDOEPHEDRINE [HSDB]

Common Name

English

(+)-THREO-EPHEDRINE

Common Name

English

PSEUDOEPHEDRINE [MI]

Common Name

English

PSEUDOEPHEDRINE [MART.]

Common Name

English

Pseudoephedrine [WHO-DD]

Common Name

English

ISOEPHEDRINE, D-

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,R*))-

Systematic Name

English

(+)-PSEUDOEPHEDRINE

Common Name

English

PSEUDOEPHEDRINE, (+)-

Common Name

English

NEODURASINA

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QR01BA02