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
Molecular Formula C9H13NO
Molecular Weight 151.2056
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 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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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
157
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Agonist
2752
Agonist
2752
 9.8 µM [Ki]
Agonist
2752
 280.0 µM [EC50]
Agonist
2752
 8.4 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Primary
Not Provided
511
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Withdrawn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
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
healthy, 14
Health Status: healthy
Age Group: 14
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
Disc. AE: Cardiomyopathy...
AEs leading to
discontinuation/dose reduction:
Cardiomyopathy
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
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
healthy, 25
Health Status: healthy
Age Group: 25
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
unhealthy, 31
Health Status: unhealthy
Age Group: 31
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Disc. AE: Vomiting, Hypertension...
AEs leading to
discontinuation/dose reduction:
Vomiting
Hypertension
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
healthy, 56
Health Status: healthy
Age Group: 56
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (severe)
Vomiting
Intracranial hemorrhage
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
AEs

AEs

AESignificanceDosePopulation
Cardiomyopathy Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
healthy, 14
Health Status: healthy
Age Group: 14
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7901355
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
healthy, 25
Health Status: healthy
Age Group: 25
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/12734532
Hypertension Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
unhealthy, 31
Health Status: unhealthy
Age Group: 31
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Vomiting Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
unhealthy, 31
Health Status: unhealthy
Age Group: 31
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/7055513
Intracranial hemorrhage Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
healthy, 56
Health Status: healthy
Age Group: 56
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Vomiting Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
healthy, 56
Health Status: healthy
Age Group: 56
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
Headache severe
Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
healthy, 56
Health Status: healthy
Age Group: 56
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4002267
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
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.
2015-01
Khat use and neurobehavioral functions: suggestions for future studies.
2010-12-01
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).
2010-07-15
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.
2010-05
Ephedra alkaloids inhibit platelet aggregation.
2010-04
Proof of principle: The effect of antimuscarinics on bladder filling sensations in healthy subjects--a placebo controlled double blind investigation using 4 and 8 mg tolterodine extended release.
2010-03
Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation.
2009-06-05
Comparison of fesoterodine and tolterodine in patients with overactive bladder.
2008-11
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.
2008-11
How many drugs for LUTS due to BPH are too many?
2008-09
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.
2008-05
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007-08
Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones.
2007-04
Treatment of men with lower urinary tract symptoms and overactive bladder.
2007-03-21
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.
2006-12
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.
2006-09-12
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006-07
Tolterodine.
2006-06-21
Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia.
2006-04
Using anticholinergics to treat overactive bladder: the issue of treatment tolerability.
2006-03
Juvenile pig detrusor: effects of propiverine and three of its metabolites.
2005-11-07
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005-10-15
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.
2005-07
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
Validation of the urgency perception scale.
2005-03
[Therapy of bladder weakness].
2005-01-21
Pharmacological management of overactive bladder : a systematic and critical review of published economic evaluations.
2005
Impact of a health education intervention in overactive bladder patients.
2004-12
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004-09-03
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.
2004-07
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.
2004-02-06
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.
2003-08-21
Use of Ephedra-containing products and risk for hemorrhagic stroke.
2003-01-14
Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder.
2003-01
Adrenergic drugs for urinary incontinence in adults.
2003
Different responses to drugs against overactive bladder in detrusor muscle of pig, guinea pig and mouse.
2002-11-01
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
2002-10
A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder.
2002-09
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.
2002-03-28
Don't be so quick to ban medications.
2002-01-08
Pharmacological properties of A-204176, a novel and selective alpha1A adrenergic agonist, in in vitro and in vivo models of urethral function.
2001-11-30
Tolterodine: an overview.
2001-11
Clarification--Drug risk in patients with glaucoma.
2001-06-11
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.
2001-03
Dystonic reaction following recommended use of a cold syrup.
1995-12
Phenylpropanolamine-induced psychosis. Potential predisposing factors.
1994-09
Alpha and beta adrenergic receptor involvement in catecholamine-induced growth of gram-negative bacteria.
1993-01-29
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987-02
Intracranial hemorrhages due to phenylpropanolamine.
1985-05-01
Patents

Patents

JP2000516204A
66
JP2001335473A
9
JP2003511458A
19
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:17:52 GMT 2025
Edited
by admin
on Mon Mar 31 18:17:52 GMT 2025
Record UNII
33RU150WUN
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
FANSIA
Preferred Name English
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
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 Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
WHO-VATC QR01BA51
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
WHO-VATC QR01BA01
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
DEA NO. 1225
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
WHO-VATC QG04BX91
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
WHO-ATC R01BA51
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
NCI_THESAURUS C87053
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
CFR 21 CFR 1315.13
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
CFR 21 CFR 1314.20
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
CFR 21 CFR 520.1760
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL61006
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
FDA UNII
33RU150WUN
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
MERCK INDEX
m8687
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
PHENYLPROPANOLAMINE
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
NCI_THESAURUS
C29364
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
DRUG CENTRAL
2149
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
INN
4955
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
CAS
14838-15-4
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
DAILYMED
33RU150WUN
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
RXCUI
8175
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY RxNorm
EVMPD
SUB09790MIG
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
NSC
9920
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
SMS_ID
100000082264
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID4023466
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
CHEBI
8104
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
HSDB
6485
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
DRUG BANK
DB00397
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
ECHA (EC/EINECS)
238-900-2
Created by admin on Mon Mar 31 18:17:52 GMT 2025 , Edited by admin on Mon Mar 31 18:17:52 GMT 2025
PRIMARY
Related Record Type Details
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of PHENYLPROPANOLAMINE MALEATE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
4-METHYLAMINOREX
PARENT->PRECURSOR
Structure of PHENYLPROPANOLAMINE BITARTRATE
SALT/SOLVATE -> PARENT
Structure of PHENYLPROPANOLAMINE SULFATE
SALT/SOLVATE -> PARENT
Structure of PHENYLPROPANOLAMINE, (-)-
ENANTIOMER -> RACEMATE
AMINE OXIDASE (FLAVIN-CONTAINING) A
METABOLIC ENZYME -> INHIBITOR
PHENYLPROPANOLAMINE POLISTIREX
SUB_CONCEPT->SUBSTANCE
Structure of PHENYLPROPANOLAMINE, (+)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of AMPHETAMINE
PARENT -> METABOLITE ACTIVE
Related Record Type Details
Structure of SELEGILINE HYDROCHLORIDE
PARENT -> IMPURITY
Structure of AMPHETAMINE
PARENT -> IMPURITY
Related Record Type Details
Structure of PHENYLPROPANOLAMINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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