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 172 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 8146	5.6 µM [IC50]
Norepinephrine transporter 183 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 8146	1.18 µM [IC50]
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796	Agonist 2637
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10449190	Agonist 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nasal congestion 26 Sources: https://www.drugs.com/ppa/pseudoephedrine.html	Primary		Approved 8307	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
Epinephrine analogues.	2001 Nov	12806441
[Separation and determination of pseudoephedrine in bufferin cold tablet by capillary electrophoresis with hydropropyl-beta-cyclodextrin as chiral selective reagent].	2001 Nov	12545473
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
[An open label multi-center clinical trial to evaluate the efficacy of compound pseudoephedrine [corrected] hydrochloride sustained release capsules in patients with nasal symptoms associated with common cold].	2002 Aug	12421505
Generalized dermatitis due to pseudoephedrine.	2002 Aug	12121199
Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase.	2002 Dec 26	12489935
Pseudoephedrine causing mania-like symptoms.	2002 Feb 22	11913943
Immediate hypersensitivity due to pseudoephedrine.	2002 Jan	11991291
Acoustic rhinometry in the dog: a novel large animal model for studies of nasal congestion.	2002 Jan-Feb	11895194
Modifying the bitterness of selected oral pharmaceuticals with cation and anion series of salts.	2002 Jul	12180534
Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit.	2002 Jul	12141718
Erythrodermia to pseudoephedrine in a patient with contact allergy to phenylephrine.	2002 Jul-Aug	12199969
Rapid simultaneous determination of amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, and 3,4-methylenedioxyethylamphetamine in urine by solid-phase extraction and GC-MS: a method optimized for high-volume laboratories.	2002 Jul-Aug	12166811
A comparative study of the side effects between pseudoephedrine in Loratadine plus Pseudoephedrine Sulfate Repetabs Tables and loratadine + pseudoephedrine tablet in treatment of allergic rhinitis in Thai patients.	2002 Jun	12322847
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.	2002 Jun	12087345
Oral medications.	2002 Mar	12012745
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
Pigmented purpuric dermatosis due to pseudoephedrine.	2002 May	12084086
Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.	2002 May 30	12027658
[Bacteremia caused by coagulase-negative staphylococci: incidence, frequency of teicoplanin resistance and molecular epidemiology].	2002 Nov	12490419
A moderate dose of pseudoephedrine does not alter muscle contraction strength or anaerobic power.	2002 Nov	12466695
Enantiomeric separation of methamphetamine and related analogs by capillary zone electrophoresis: intelligence study in routine methamphetamine seizures.	2002 Nov	12455645
Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites.	2002 Nov 29	12444610
[Blood supply of the lips].	2002 Oct	12449862
Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions.	2002 Oct	12382047
Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers.	2002 Oct	12373557
Severe adverse drug reactions due to pseudoephedrine from over-the-counter medications.	2002 Sep	12492550
[Toxic dermatitis caused by pseudoephedrine: apropos of a case].	2002 Sep	12389444
Pharmacokinetic interaction study of a fixed combination of 500 mg acetylsalicylic acid/30 mg pseudoephedrine versus each of the single active ingredients in healthy male volunteers.	2003	12785122
Baboon syndrome due to pseudoephedrine.	2003 Apr	12786741
[Improving the medical treatment of minors who are victims of sexual assault or physical abuse: a receiving center and partnership between a psychiatric hospital and university hospital].	2003 Apr	12784493
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
Nonpigmenting solitary fixed drug eruption caused by a Chinese traditional herbal medicine, ma huang (Ephedra Hebra), mainly containing pseudoephedrine and ephedrine.	2003 Apr	12664035
Controlled porosity osmotic pump-based controlled release systems of pseudoephedrine. I. Cellulose acetate as a semipermeable membrane.	2003 Apr 14	12695059
Separation and determination of ephedrine and pseudoephedrine by combination of flow injection with capillary electrophoresis.	2003 Jan	12597588
Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise.	2003 Jan	12582945
Efficacy and safety of clemastine-pseudoephedrine-acetaminophen versus pseudoephedrine-acetaminophen in the treatment of seasonal allergic rhinitis in a 1-day, placebo-controlled park study.	2003 Jan	12546342
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.	2003 Jul	12791938
Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction.	2003 Jul 5	12798180
Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry.	2003 Jun	12783454
[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
Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method.	2003 Mar 26	12644207
In vitro evaluation of apical microleakage following canal filling with a coated carrier system compared with lateral and thermomechanical Gutta-Percha condensation techniques.	2003 May	12752651
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
Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule.	2003 May 1	12725239
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 `Fri Dec 16 16:53:33 UTC 2022` Edited by `admin` on `Fri Dec 16 16:53:33 UTC 2022`
Record UNII	7CUC9DDI9F
Record Status	`Validated (UNII)`
Record Version

Download

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