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

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
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
n = 1
Health Status: unknown
Age Group: 16 years
Sex: F
Population Size: 1
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 1
Health Status: unhealthy
Age Group: 3 years
Sex: M
Population Size: 1
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
Co-administed with::
acetominophen(500 mg twice daily, oral)
Sources:
unhealthy, 37 years
n = 1
Health Status: unhealthy
Condition: sinusitis
Age Group: 37 years
Sex: F
Population Size: 1
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
n = 38
Health Status: unhealthy
Age Group: 38.8 years
Sex: M+F
Population Size: 38
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
n = 1
Health Status: unhealthy
Condition: upper airway infection
Age Group: 44 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: chronic sinusitis | allergic rhinitis
Age Group: 46 years
Sex: F
Population Size: 1
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
Co-administed with::
acetominophen(500 mg twice daily, oral)
chlorpheniramine maleate(2 mg; twice daily, oral)
Sources:
unhealthy, 50 years
n = 1
Health Status: unhealthy
Condition: rhinitis
Age Group: 50 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 87 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unknown
Age Group: 16 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unknown
Age Group: 16 years
Sex: F
Population Size: 1
Sources:
Rhabdomyolysis 1 patient
1500 mg single, oral
Overdose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 16 years
n = 1
Health Status: unknown
Age Group: 16 years
Sex: F
Population Size: 1
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 17
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 17
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
n = 1
Health Status: unhealthy
Age Group: 3 years
Sex: M
Population Size: 1
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
Co-administed with::
acetominophen(500 mg twice daily, oral)
Sources:
unhealthy, 37 years
n = 1
Health Status: unhealthy
Condition: sinusitis
Age Group: 37 years
Sex: F
Population Size: 1
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
Co-administed with::
acetominophen(500 mg twice daily, oral)
Sources:
unhealthy, 37 years
n = 1
Health Status: unhealthy
Condition: sinusitis
Age Group: 37 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: upper airway infection
Age Group: 44 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: upper airway infection
Age Group: 44 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: chronic sinusitis | allergic rhinitis
Age Group: 46 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Condition: chronic sinusitis | allergic rhinitis
Age Group: 46 years
Sex: F
Population Size: 1
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
Co-administed with::
acetominophen(500 mg twice daily, oral)
chlorpheniramine maleate(2 mg; twice daily, oral)
Sources:
unhealthy, 50 years
n = 1
Health Status: unhealthy
Condition: rhinitis
Age Group: 50 years
Sex: F
Population Size: 1
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
Co-administed with::
acetominophen(500 mg twice daily, oral)
chlorpheniramine maleate(2 mg; twice daily, oral)
Sources:
unhealthy, 50 years
n = 1
Health Status: unhealthy
Condition: rhinitis
Age Group: 50 years
Sex: F
Population Size: 1
Sources:
Hypertension 1 patient
720 mg single, oral
Overdose
Dose: 720 mg
Route: oral
Route: single
Dose: 720 mg
Sources:
unhealthy, 87 years
n = 1
Health Status: unhealthy
Age Group: 87 years
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
A Double-blind crossover trial of pseudoephedrine and triprolidine, alone and in combination, for the treatment of allergenic rhinitis.
1975 Jan
Dextromethorphan- and pseudoephedrine-induced agitated psychosis and ataxia: case report.
1999 Mar-Apr
Angle closure risk from proprietary medicines.
2001 Apr
Hypokalemic metabolic acidosis attributed to cough mixture abuse.
2001 Aug
Aziridine ring-opening reactions with chiral enolates. Stereocontrolled synthesis of 5-substituted-3-methyl-pyrrolidin-2-ones.
2001 Aug 24
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
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.
2001 Jan-Feb
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.
2001 Jun
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
[Cost effectiveness of GM-CSF in the treatment of acute myeloblastic leukemia in aged patients: protocol of GOELAM Sa3].
2001 Mar-Apr
Factitious hypertension by pseudoephedrine.
2001 Mar-Apr
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid.
2001 May
Epinephrine analogues.
2001 Nov
Chloroephedrine: contaminant of methamphetamine synthesis with cardiovascular activity.
2001 Nov 1
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.
2001 Sep
Toxicity of over-the-counter cough and cold medications.
2001 Sep
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.
2001 Sep 5
Myocardial infarction temporally related to ephedra--a possible role for the coronary microcirculation.
2002
Pseudoephedrine causing mania-like symptoms.
2002 Feb 22
Maternal medication use and risks of gastroschisis and small intestinal atresia.
2002 Jan 1
Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit.
2002 Jul
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.
2002 Jun
[Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients].
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
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
Surfing, self-medicating and safety: buying non-prescription and complementary medicines via the internet.
2003 Apr
Separation and determination of ephedrine and pseudoephedrine by combination of flow injection with capillary electrophoresis.
2003 Jan
Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction.
2003 Jul 5
Safety of selegiline with cold medications.
2003 Mar
Adrenaline given outside the context of life threatening allergic reactions.
2003 Mar 15
Canine model of nasal congestion and allergic rhinitis.
2003 May
Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule.
2003 May 1
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 Sat Dec 16 19:27:40 GMT 2023
Edited
by admin
on Sat Dec 16 19:27:40 GMT 2023
Record UNII
X7TX4R5VWL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Pseudoephedrine Hydrobromide
Common Name English
Pseudoephedrine Hydrobromide [WHO-DD]
Common Name English
Benzenemethanol, α-[(1S)-1-(methylamino)ethyl]-, hydrobromide (1:1), (αS)-
Systematic Name English
Benzenemethanol, α-[1-(methylamino)ethyl]-, hydrobromide, [S-(R*,R*)]-
Systematic Name English
Code System Code Type Description
CAS
60706-27-6
Created by admin on Sat Dec 16 19:27:40 GMT 2023 , Edited by admin on Sat Dec 16 19:27:40 GMT 2023
PRIMARY
PUBCHEM
67679722
Created by admin on Sat Dec 16 19:27:40 GMT 2023 , Edited by admin on Sat Dec 16 19:27:40 GMT 2023
PRIMARY
FDA UNII
X7TX4R5VWL
Created by admin on Sat Dec 16 19:27:40 GMT 2023 , Edited by admin on Sat Dec 16 19:27:40 GMT 2023
PRIMARY
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