U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO
Molecular Weight 151.2056
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE

SMILES

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

InChI

InChIKey=DLNKOYKMWOXYQA-CBAPKCEASA-N
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/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 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 is mainly used as a nasal decongestant. Phenylpropanolamine is also used as anorexiant in obesity and to treat urinary incontinence in veteranary. Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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
158
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Agonist
2678
Agonist
2678
 9.8 µM [Ki]
Agonist
2678
 280.0 µM [EC50]
Agonist
2678
 8.4 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
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Withdrawn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Withdrawn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

2000
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
Positive phentolamine test in hypertension induced by a nasal decongestant.
1969 Apr 17
Phenylpropanolamine-associated headache.
1985 Apr
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Intracerebral hemorrhage and phenylpropanolamine use.
1987 Mar
Alpha and beta adrenergic receptor involvement in catecholamine-induced growth of gram-negative bacteria.
1993 Jan 29
Phenylpropanolamine-induced psychosis. Potential predisposing factors.
1994 Sep
Dystonic reaction following recommended use of a cold syrup.
1995 Dec
Failure of tolterodine to treat clozapine-induced nocturnal enuresis.
2001 Jul-Aug
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
Tolterodine: an overview.
2001 Nov
The effect of tolterodine on the pharmacokinetics and pharmacodynamics of a combination oral contraceptive containing ethinyl estradiol and levonorgestrel.
2001 Nov
Maternal medication use and risks of gastroschisis and small intestinal atresia.
2002 Jan 1
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
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
A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder.
2002 Sep
Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder.
2003 Jan
Quantifying errors without random sampling.
2003 Jun 12
The fitness of copings constructed over UCLA abutments and the implant, constructed by different techniques: casting and casting with laser welding.
2004 Dec
Hidden amphetamines: from smoking cessation to diabetes.
2004 Feb
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.
2004 Jul
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
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Validation of the urgency perception scale.
2005 Mar
Tolterodinium (+)-(2R,3R)-hydrogen tartrate.
2005 Mar
Juvenile pig detrusor: effects of propiverine and three of its metabolites.
2005 Nov 7
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia.
2006 Apr
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.
2006 Dec
Use of oral decongestants during pregnancy and delivery outcome.
2006 Feb
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006 Jul
[Stroke and phenylpropanolamine: what risk factors and what recommendations in request?].
2007
Mixed urinary incontinence: continuing to confound?
2007 Dec
Efficacy and safety of combined therapy with terazosin and tolteradine for patients with lower urinary tract symptoms associated with benign prostatic hyperplasia: a prospective study.
2007 Mar 5
Extended-release tolterodine with or without tamsulosin in men with lower urinary tract symptoms and overactive bladder: effects on urinary symptoms assessed by the International Prostate Symptom Score.
2008 Nov
How many drugs for LUTS due to BPH are too many?
2008 Sep
Mean arterial pressure: therapeutic goals and pharmacologic support.
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
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).
2010 Jul 15
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.
2010 May
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 (Phenylpropanolamine) orally every 4 hours
Route of Administration: Nasal
In Vitro Use Guide
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Name Type Language
PHENYLPROPANOLAMINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
PROPADRINE
Common Name English
RINEXIN
Brand Name English
NSC-9920
Code English
PHENYLPROPANOLAMINE [MI]
Common Name English
FANSIA
Brand Name English
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, (R*,S*)-, (±)-
Common Name English
Phenylpropanolamine [WHO-DD]
Common Name English
NOREPHEDRINE
Common Name English
(±)-NOREPHEDRINE
Common Name English
PHENYLPROPANOLAMINE [HSDB]
Common Name English
PHENYLPROPANOLAMINE [MART.]
Common Name English
PHENYLPROPANOLAMINE [VANDF]
Common Name English
phenylpropanolamine [INN]
Common Name English
SELEGILINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
PHENYLFENESIN
Common Name English
Classification Tree Code System Code
WHO-ATC R01BA01
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
WHO-VATC QR01BA51
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
WHO-VATC QR01BA01
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
DEA NO. 1225
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
WHO-VATC QG04BX91
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
WHO-ATC R01BA51
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
NCI_THESAURUS C87053
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
CFR 21 CFR 1315.13
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
CFR 21 CFR 1314.20
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
CFR 21 CFR 520.1760
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL61006
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
FDA UNII
33RU150WUN
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
MERCK INDEX
m8687
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PHENYLPROPANOLAMINE
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
NCI_THESAURUS
C29364
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
DRUG CENTRAL
2149
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
INN
4955
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
CAS
14838-15-4
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
PUBCHEM
10297
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
DAILYMED
33RU150WUN
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
RXCUI
8175
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY RxNorm
EVMPD
SUB09790MIG
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
NSC
9920
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
SMS_ID
100000082264
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
CHEBI
8104
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
HSDB
6485
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
DRUG BANK
DB00397
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
238-900-2
Created by admin on Fri Dec 15 16:03:48 GMT 2023 , Edited by admin on Fri Dec 15 16:03:48 GMT 2023
PRIMARY
PARENT (METABOLITE ACTIVE)
Structure of AMPHETAMINE
SALT/SOLVATE (PARENT)
Structure of PHENYLPROPANOLAMINE MALEATE
SALT/SOLVATE (PARENT)
Structure of PHENYLPROPANOLAMINE SULFATE
NIH
NCATS
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DISCLAIMER
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