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Details

Stereochemistry RACEMIC
Molecular Formula 2C9H13NO.H2O4S
Molecular Weight 400.49
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE SULFATE

SMILES

OS(O)(=O)=O.C[C@H](N)[C@H](O)C1=CC=CC=C1.C[C@H](N)[C@H](O)C2=CC=CC=C2

InChI

InChIKey=QSGAFDSLNHRMIQ-SMBKYJPPSA-N
InChI=1S/2C9H13NO.H2O4S/c2*1-7(10)9(11)8-5-3-2-4-6-8;1-5(2,3)4/h2*2-7,9,11H,10H2,1H3;(H2,1,2,3,4)/t2*7-,9-;/m00./s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.druginfosys.com/drug.aspx?drugcode=569&type=1 | https://www.drugs.com/dosage/phenylpropanolamine.html | https://www.petcarerx.com/medication-guides/about-the-proin-dosage-for-urinary-incontinence/1086?page=all | https://www.federalregister.gov/documents/2014/02/20/2014-03596/phenylpropanolamine-withdrawal-of-approval-of-13-new-drug-applications-and-7-abbreviated-new-drug

(+)-Phenylpropanolamine is an enantiomer of propanolamine. The substance has low adrenergic activity and exerts measurable physiological effect only at high doses, which were lethal to experimental animals tested. Phenylpropanolamine belongs to the sympathomimetic amine class of drugs and is structurally related to ephedrine. The effects of phenylpropanolamine are largely the result of alpha-adrenergic agonist activity resulting from both direct stimulation of adrenergic receptors and release of neuronal norepinephrine. Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.

CNS Activity

Originator

Mannich, C.|Jacobsohn, W.
9
Sources: C. Mannich and W. Jacobsohn, Ber., 43, 189 (1910).
Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihub

Approval Year

1941
190
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2637
Agonist
2637
Agonist
2637
 9.8 µM [Ki]
Agonist
2637
 280.0 µM [EC50]
Agonist
2637
 8.4 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
505
Unknown

Approved Use

Unknown
Primary
Not Provided
505
Unknown

Approved Use

Unknown
Primary
Withdrawn
PHENYLPROPANOLAMINE

Approved Use

Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Primary
Withdrawn
PHENYLPROPANOLAMINE

Approved Use

Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Primary
Withdrawn
CODAMINE

Approved Use

Unknown

Launch Date

9.700992E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
107 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11361053/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1104 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11361053/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11361053/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Co-administed with::
brompheniramine, p.o(36 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
Page: p.825
Disc. AE: Cardiomyopathy...
AEs leading to
discontinuation/dose reduction:
Cardiomyopathy
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
Page: p.825
25 mg 2 times / day multiple, oral
Recommended
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Page: p.100
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Page: p.100
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
Disc. AE: Vomiting, Hypertension...
AEs leading to
discontinuation/dose reduction:
Vomiting
Hypertension
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (severe)
Vomiting
Intracranial hemorrhage
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
AEs

AEs

AESignificanceDosePopulation
Cardiomyopathy Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Co-administed with::
brompheniramine, p.o(36 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
Page: p.825
Myocardial infarction Disc. AE
25 mg 2 times / day multiple, oral
Recommended
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Page: p.100
Hypertension Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
Vomiting Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Page: p.52
Intracranial hemorrhage Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
Vomiting Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
Headache severe
Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Page: p.510
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChemIDplus
67244900
https://chem.nlm.nih.gov/chemidplus/id/0067244900
PubChem
118984428
https://pubchem.ncbi.nlm.nih.gov/compound/118984428
Wikidata
Q27274344
PubMed

PubMed

TitleDatePubMed
Phenylpropanolamine-associated headache.
1985 Apr
Phenylpropanolamine-induced psychosis. Potential predisposing factors.
1994 Sep
Dystonic reaction following recommended use of a cold syrup.
1995 Dec
Effect of tolterodine on the anticoagulant actions and pharmacokinetics of single-dose warfarin in healthy volunteers.
2002
Phenylpropanolamine appears not to promote weight loss in patients with schizophrenia who have gained weight during clozapine treatment.
2002 Apr
Different responses to drugs against overactive bladder in detrusor muscle of pig, guinea pig and mouse.
2002 Nov 1
Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial.
2002 Oct
HPLC determination of phenylpropanolamine in pharmaceutical OTC preparations.
2002 Oct
A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder.
2002 Sep
Adrenergic drugs for urinary incontinence in adults.
2003
Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder.
2003 Jan
Use of Ephedra-containing products and risk for hemorrhagic stroke.
2003 Jan 14
Intracellular signaling pathways for norepinephrine- and endothelin-1-mediated regulation of myocardial cell apoptosis.
2004 Apr
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004 Sep 3
Nocturnal enuresis in children. A four-year experience in outpatient clinics of pediatric urology.
2005
Tolterodine for the treatment of overactive bladder: a review.
2005 Apr
Should we switch over to tolterodine in every child with non-neurogenic daytime urinary incontinence in whom oxybutynin failed?
2005 Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Determination of ephedrine and related compounds in pharmaceutical preparations by ion chromatography with direct conductivity detection.
2005 May
Juvenile pig detrusor: effects of propiverine and three of its metabolites.
2005 Nov 7
Use of oral decongestants during pregnancy and delivery outcome.
2006 Feb
Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.
2006 Jun
Relationships among symptoms, bother, and treatment satisfaction in overactive bladder patients.
2007
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.
2008 May
Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives.
2009 Dec 3
Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation.
2009 Jun 5
Ephedra alkaloids inhibit platelet aggregation.
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.
2010 May
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.
2015 Jan
Patents

Patents

JP2000516204A
66
JP2001335473A
9
JP2003511458A
17
JP2007513168A
10
JPH02133A
9
JPH10203971A
9
JPS59184168A
9

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Nasal Congestion 25 mg orally every 4 hours. -or- 75 mg orally extended release every 12 hours. Not to exceed 150 mg/day. Usual Adult Dose for Weight Loss 25 mg orally 3 times a day, one-half hour before meals. -or- 75 mg orally extended release once a day in the morning. The use of phenylpropanolamine for weight loss should be limited to 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Name Type Language
PHENYLPROPANOLAMINE SULFATE
WHO-DD  
Common Name English
Phenylpropanolamine sulfate [WHO-DD]
Common Name English
PHENYLPROPANOLAMINE SULPHATE
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
214-457-0
Created by admin on Sun Dec 18 14:54:29 UTC 2022 , Edited by admin on Sun Dec 18 14:54:29 UTC 2022
PRIMARY
PUBCHEM
76966052
Created by admin on Sun Dec 18 14:54:29 UTC 2022 , Edited by admin on Sun Dec 18 14:54:29 UTC 2022
PRIMARY
EPA CompTox
DTXSID40920970
Created by admin on Sun Dec 18 14:54:29 UTC 2022 , Edited by admin on Sun Dec 18 14:54:29 UTC 2022
PRIMARY
CAS
1130-06-9
Created by admin on Sun Dec 18 14:54:29 UTC 2022 , Edited by admin on Sun Dec 18 14:54:29 UTC 2022
PRIMARY
FDA UNII
TQA3O9M79V
Created by admin on Sun Dec 18 14:54:29 UTC 2022 , Edited by admin on Sun Dec 18 14:54:29 UTC 2022
PRIMARY
NIH
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