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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO.BrH
Molecular Weight 246.144
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pseudoephedrine Hydrobromide

SMILES

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

InChI

InChIKey=VGBAPRQRVHQDMK-KXNXZCPBSA-N
InChI=1S/C10H15NO.BrH/c1-8(11-2)10(12)9-6-4-3-5-7-9;/h3-8,10-12H,1-2H3;1H/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

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Originator

Sources: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889).
Curator's Comment: (+)-threo-isomer of ephedrine, q.v. Isoln from E. vulgaris: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889). Synthesis: E. Späth, R. Göhring, Monatsh. Chem. 41, 319 (1920). reference retrieved from http://www.drugfuture.com/chemdata/pseudoephedrine.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
292 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
4346 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.3 h
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

Doses

DosePopulationAdverse events​
1500 mg single, oral
Overdose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 16 years
Health Status: unknown
Age Group: 16 years
Sex: F
Sources:
Other AEs: Rhabdomyolysis, Creatine kinase increased...
Other AEs:
Rhabdomyolysis (1 patient)
Creatine kinase increased (1 patient)
Blood myoglobin increased (1 patient)
Sources:
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
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:
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:
unhealthy, 3 years
Health Status: unhealthy
Age Group: 3 years
Sex: M
Sources:
Disc. AE: Urinary retention...
AEs leading to
discontinuation/dose reduction:
Urinary retention (acute, 1 patient)
Sources:
30 mg 2 times / day multiple, oral
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
Disc. AE: Ischemic colitis, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Ischemic colitis (1 patient)
Abdominal pain (acute, 1 patient)
Sources:
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:
unhealthy, 38.8 years
Health Status: unhealthy
Age Group: 38.8 years
Sex: M+F
Sources:
30 mg 3 times / day multiple, oral
Dose: 30 mg, 3 times / day
Route: oral
Route: multiple
Dose: 30 mg, 3 times / day
Sources:
unhealthy, 44 years
Health Status: unhealthy
Age Group: 44 years
Sex: F
Sources:
Disc. AE: Ischemic colitis, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Ischemic colitis (1 patient)
Abdominal pain (acute, 1 patient)
Sources:
120 mg 1 times / day multiple, oral
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Disc. AE: Ischemic colitis, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Ischemic colitis (1 patient)
Abdominal pain (acute, 1 patient)
Sources:
30 mg 2 times / day multiple, oral
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
unhealthy, 50 years
Health Status: unhealthy
Age Group: 50 years
Sex: F
Sources:
Disc. AE: Ischemic colitis, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Ischemic colitis (1 patient)
Abdominal pain (acute, 1 patient)
Sources:
720 mg single, oral
Overdose
Dose: 720 mg
Route: oral
Route: single
Dose: 720 mg
Sources:
unhealthy, 87 years
Health Status: unhealthy
Age Group: 87 years
Sex: M
Sources:
Other AEs: Hypertension...
Other AEs:
Hypertension (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Blood myoglobin increased 1 patient
1500 mg single, oral
Overdose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 16 years
Health Status: unknown
Age Group: 16 years
Sex: F
Sources:
Creatine kinase increased 1 patient
1500 mg single, oral
Overdose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 16 years
Health Status: unknown
Age Group: 16 years
Sex: F
Sources:
Rhabdomyolysis 1 patient
1500 mg single, oral
Overdose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 16 years
Health Status: unknown
Age Group: 16 years
Sex: F
Sources:
Palpitations 10 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Restlessness 10 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Tension 10 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Insomnia 12 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Anxiety 13 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Dry mouth 6 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Anorexia 7 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Tachycardia 9 patients
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:
healthy, 24 years
Health Status: healthy
Age Group: 24 years
Sex: M
Sources:
Urinary retention acute, 1 patient
Disc. AE
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:
unhealthy, 3 years
Health Status: unhealthy
Age Group: 3 years
Sex: M
Sources:
Ischemic colitis 1 patient
Disc. AE
30 mg 2 times / day multiple, oral
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
Abdominal pain acute, 1 patient
Disc. AE
30 mg 2 times / day multiple, oral
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: F
Sources:
Ischemic colitis 1 patient
Disc. AE
30 mg 3 times / day multiple, oral
Dose: 30 mg, 3 times / day
Route: oral
Route: multiple
Dose: 30 mg, 3 times / day
Sources:
unhealthy, 44 years
Health Status: unhealthy
Age Group: 44 years
Sex: F
Sources:
Abdominal pain acute, 1 patient
Disc. AE
30 mg 3 times / day multiple, oral
Dose: 30 mg, 3 times / day
Route: oral
Route: multiple
Dose: 30 mg, 3 times / day
Sources:
unhealthy, 44 years
Health Status: unhealthy
Age Group: 44 years
Sex: F
Sources:
Ischemic colitis 1 patient
Disc. AE
120 mg 1 times / day multiple, oral
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Abdominal pain acute, 1 patient
Disc. AE
120 mg 1 times / day multiple, oral
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Ischemic colitis 1 patient
Disc. AE
30 mg 2 times / day multiple, oral
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
unhealthy, 50 years
Health Status: unhealthy
Age Group: 50 years
Sex: F
Sources:
Abdominal pain acute, 1 patient
Disc. AE
30 mg 2 times / day multiple, oral
Dose: 30 mg, 2 times / day
Route: oral
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
unhealthy, 50 years
Health Status: unhealthy
Age Group: 50 years
Sex: F
Sources:
Hypertension 1 patient
720 mg single, oral
Overdose
Dose: 720 mg
Route: oral
Route: single
Dose: 720 mg
Sources:
unhealthy, 87 years
Health Status: unhealthy
Age Group: 87 years
Sex: M
Sources:
PubMed

PubMed

TitleDatePubMed
Cetirizine/pseudoephedrine.
2001
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
Epinephrine analogues.
2001 Nov
[Separation and determination of pseudoephedrine in bufferin cold tablet by capillary electrophoresis with hydropropyl-beta-cyclodextrin as chiral selective reagent].
2001 Nov
Chloroephedrine: contaminant of methamphetamine synthesis with cardiovascular activity.
2001 Nov 1
Biotransformation of benzaldehyde into (R)-phenylacetylcarbinol by filamentous fungi or their extracts.
2001 Oct
Acute psychosis due to the interaction of legal compounds--ephedra alkaloids in 'vigueur fit' tablets, caffeine in 'red bull' and alcohol.
2001 Oct
Small-cell carcinoma of the esophagus: report of three cases and review of the literature with emphasis on therapy.
2001 Sep
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.
2001 Sep
Analysis of enantiomers giving partially overlapped peaks by using different treatments of the chromatographic ultraviolet signals: quantification of pseudoephedrine enantiomers.
2001 Sep 28
Myocardial infarction temporally related to ephedra--a possible role for the coronary microcirculation.
2002
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
[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
Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase.
2002 Dec 26
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.
2002 Feb 15
Pseudoephedrine causing mania-like symptoms.
2002 Feb 22
Immediate hypersensitivity due to pseudoephedrine.
2002 Jan
Maternal medication use and risks of gastroschisis and small intestinal atresia.
2002 Jan 1
Rapid determination of pseudoephedrine in human plasma by high-performance liquid chromatography.
2002 Jan 25
Cerebral vasoconstriction and stroke after use of serotonergic drugs.
2002 Jan 8
Pharmacological characterization of a noninvasive, chronic, experimental dog model of nasal congestion.
2002 Jan-Feb
Acoustic rhinometry in the dog: a novel large animal model for studies of nasal congestion.
2002 Jan-Feb
Modifying the bitterness of selected oral pharmaceuticals with cation and anion series of salts.
2002 Jul
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
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
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.
2002 Jun
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
Pigmented purpuric dermatosis due to pseudoephedrine.
2002 May
Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.
2002 May 30
[Bacteremia caused by coagulase-negative staphylococci: incidence, frequency of teicoplanin resistance and molecular epidemiology].
2002 Nov
A moderate dose of pseudoephedrine does not alter muscle contraction strength or anaerobic power.
2002 Nov
Enantiomeric separation of methamphetamine and related analogs by capillary zone electrophoresis: intelligence study in routine methamphetamine seizures.
2002 Nov
Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites.
2002 Nov 29
Quantitative and structural determination of pseudoephedrine sulfate and its related compounds in pharmaceutical preparations using high-performance liquid chromatography.
2002 Nov 7
[Blood supply of the lips].
2002 Oct
[Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients].
2002 Oct
Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions.
2002 Oct
Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers.
2002 Oct
Severe adverse drug reactions due to pseudoephedrine from over-the-counter medications.
2002 Sep
[Toxic dermatitis caused by pseudoephedrine: apropos of a case].
2002 Sep
Efficacy of once-daily desloratadine/pseudoephedrine for relief of nasal congestion.
2002 Sep-Oct
Separation and determination of ephedrine and pseudoephedrine by combination of flow injection with capillary electrophoresis.
2003 Jan
Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise.
2003 Jan
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
Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry.
2003 Jun
[Tobacco: knowledge, reasoning and opinion of high school students in Doubs. Reflections on prevention].
2003 Mar
Safety of selegiline with cold medications.
2003 Mar
Adrenaline given outside the context of life threatening allergic reactions.
2003 Mar 15
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
Canine model of nasal congestion and allergic rhinitis.
2003 May
Patents

Sample Use Guides

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
Curator's Comment: Pseudoephedrine inhibits interleukin-2 (IL-2) and tumor necrosis factor (TNF) alpha-gene transcription in stimulated Jurkat cells, a human T-cell leukemia cell line.
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 15:45:02 GMT 2025
Edited
by admin
on Wed Apr 02 15:45:02 GMT 2025
Record UNII
X7TX4R5VWL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Pseudoephedrine Hydrobromide
Common Name English
Pseudoephedrine Hydrobromide [WHO-DD]
Preferred Name English
Benzenemethanol, ?-[(1S)-1-(methylamino)ethyl]-, hydrobromide (1:1), (?S)-
Systematic Name English
Benzenemethanol, ?-[1-(methylamino)ethyl]-, hydrobromide, [S-(R*,R*)]-
Systematic Name English
Code System Code Type Description
SMS_ID
300000050401
Created by admin on Wed Apr 02 15:45:02 GMT 2025 , Edited by admin on Wed Apr 02 15:45:02 GMT 2025
PRIMARY
CAS
60706-27-6
Created by admin on Wed Apr 02 15:45:02 GMT 2025 , Edited by admin on Wed Apr 02 15:45:02 GMT 2025
PRIMARY
PUBCHEM
67679722
Created by admin on Wed Apr 02 15:45:02 GMT 2025 , Edited by admin on Wed Apr 02 15:45:02 GMT 2025
PRIMARY
FDA UNII
X7TX4R5VWL
Created by admin on Wed Apr 02 15:45:02 GMT 2025 , Edited by admin on Wed Apr 02 15:45:02 GMT 2025
PRIMARY
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