U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO.ClH
Molecular Weight 187.667
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=DYWNLSQWJMTVGJ-KUSKTZOESA-N
InChI=1S/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H/t7-,9-;/m0./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C9H13NO
Molecular Weight 151.2056
Charge 0
Count
Stereochemistry RACEMIC
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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
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
Clarification--Drug risk in patients with glaucoma.
2001 Jun 11
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.
2001 Mar
Tolterodine: an overview.
2001 Nov
Pharmacological properties of A-204176, a novel and selective alpha1A adrenergic agonist, in in vitro and in vivo models of urethral function.
2001 Nov 30
Don't be so quick to ban medications.
2002 Jan 8
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
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
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
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.
2003 Aug 21
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
Impact of a health education intervention in overactive bladder patients.
2004 Dec
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.
2004 Feb 6
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
Pharmacological management of overactive bladder : a systematic and critical review of published economic evaluations.
2005
[Therapy of bladder weakness].
2005 Jan 21
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
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
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006 Jul
Tolterodine.
2006 Jun 6-12
Using anticholinergics to treat overactive bladder: the issue of treatment tolerability.
2006 Mar
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.
2006 Sep 12
Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones.
2007 Apr
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007 Aug
Treatment of men with lower urinary tract symptoms and overactive bladder.
2007 Mar 21
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.
2008 May
Comparison of fesoterodine and tolterodine in patients with overactive bladder.
2008 Nov
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
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
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).
2010 Jul 15
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 Mar
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
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 18:25:53 GMT 2025
Edited
by admin
on Mon Mar 31 18:25:53 GMT 2025
Record UNII
8D5I63UE1Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-23798
Preferred Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
PROPADRINE HYDROCHLORIDE
Common Name English
BROMANATE DC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
Phenylpropanolamine hydrochloride [WHO-DD]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [VANDF]
Common Name English
MYPHETANE DC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, HYDROCHLORIDE, (R*,S*)-, (±)-
Common Name English
BROMANATE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [JAN]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
DEMAZIN COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
DIMETAPP COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
(±)-NOREPHEDRINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
TRIAMINIC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
CONTAC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
DRIZE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [USP-RS]
Common Name English
BIPHETAP COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
HYCOMINE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [MART.]
Common Name English
BROMATAPP COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
TAVIST-D COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [MI]
Common Name English
PHENYLPROPANOLAMINE HCL
Common Name English
ORNADE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
DIMETANE-DC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
CODAMINE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C87053
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
205-826-7
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
DRUG BANK
DBSALT000996
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
NCI_THESAURUS
C66379
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
DAILYMED
8D5I63UE1Q
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
CAS
154-41-6
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
ChEMBL
CHEMBL61006
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
RXCUI
3266
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m8687
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY Merck Index
FDA UNII
8D5I63UE1Q
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
EVMPD
SUB14842MIG
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
SMS_ID
100000091354
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
RS_ITEM_NUM
1534005
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID2025896
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
NSC
23798
Created by admin on Mon Mar 31 18:25:53 GMT 2025 , Edited by admin on Mon Mar 31 18:25:53 GMT 2025
PRIMARY
Related Record Type Details
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE, (-)-
ENANTIOMER -> RACEMATE
Structure of PHENYLPROPANOLAMINE
PARENT -> SALT/SOLVATE
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE
BASIS OF STRENGTH->SUBSTANCE
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE
BASIS OF STRENGTH->SUBSTANCE
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE, (+)-
ENANTIOMER -> RACEMATE
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE
BASIS OF STRENGTH->SUBSTANCE
Related Record Type Details
Structure of CATHINONE HYDROCHLORIDE
IMPURITY -> PARENT
IMPURITY (UV)
USP
Related Record Type Details
Structure of PHENYLPROPANOLAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966