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

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 C9H13NO
Molecular Weight 151.2056
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.

Originator

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
PHENYLPROPANOLAMINE

Approved Use

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

Approved Use

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

Approved Use

Unknown

Launch Date

2000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
107 ng/mL
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
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
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: Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources: Page: p.825
Disc. AE: Cardiomyopathy...
AEs leading to
discontinuation/dose reduction:
Cardiomyopathy
Sources: 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: Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.100
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Sources: 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: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Disc. AE: Vomiting, Hypertension...
AEs leading to
discontinuation/dose reduction:
Vomiting
Hypertension
Sources: 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: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (severe)
Vomiting
Intracranial hemorrhage
Sources: 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: Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources: 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: Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources: 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: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: 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: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: 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: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: 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: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: 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: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
PubMed

PubMed

TitleDatePubMed
Phenylpropanolamine-associated headache.
1985 Apr
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
[Cerebral hemorrhage associated with the use of phenylpropanolamine. Clinical cases].
1996 Dec
The overactive bladder in children: a potential future indication for tolterodine.
2001 Apr
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.
2001 Jun
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
Intense and recurrent déjà vu experiences related to amantadine and phenylpropanolamine in a healthy male.
2001 Sep
Effect of tolterodine on the anticoagulant actions and pharmacokinetics of single-dose warfarin in healthy volunteers.
2002
Maternal medication use and risks of gastroschisis and small intestinal atresia.
2002 Jan 1
Don't be so quick to ban medications.
2002 Jan 8
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
2002 Oct
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
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
Intracellular signaling pathways for norepinephrine- and endothelin-1-mediated regulation of myocardial cell apoptosis.
2004 Apr
Hidden amphetamines: from smoking cessation to diabetes.
2004 Feb
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.
2004 Feb 6
Examination of aqueous oxidized cellulose dispersions as a potential drug carrier. I. Preparation and characterization of oxidized cellulose-phenylpropanolamine complexes.
2004 Oct 8
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004 Sep 3
Tolterodine for the treatment of overactive bladder: a review.
2005 Apr
Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways.
2005 Feb
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.
2005 Jul
Comparison of symptom severity and treatment response in patients with incontinent and continent overactive bladder.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.
2006 Jun
Tolterodine.
2006 Jun 6-12
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
Mixed urinary incontinence: continuing to confound?
2007 Dec
Treatment of men with lower urinary tract symptoms and overactive bladder.
2007 Mar 21
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
Effect of tolterodine on sleep structure modulated by CYP2D6 genotype.
2008 Jul
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
How many drugs for LUTS due to BPH are too many?
2008 Sep
Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives.
2009 Dec 3
Keep an eye on the pupil: developing countries under chemical attack.
2009 Jun
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
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

Sample Use Guides

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 Fri Dec 15 16:21:18 GMT 2023
Edited
by admin
on Fri Dec 15 16:21:18 GMT 2023
Record UNII
8D5I63UE1Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLPROPANOLAMINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
PROPADRINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF CONTAC
Common Name English
BROMANATE DC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
Phenylpropanolamine hydrochloride [WHO-DD]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF TRIAMINIC
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [VANDF]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF DEMAZIN
Common Name English
MYPHETANE DC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, HYDROCHLORIDE, (R*,S*)-, (±)-
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF BROMANATE DC
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF MYPHETANE DC
Common Name English
BROMANATE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [JAN]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF BROMATAPP
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF DIMETAPP
Common Name English
DEMAZIN COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF DRIZE
Common Name English
DIMETAPP COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
(±)-NOREPHEDRINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF DIMETANE-DC
Common Name English
TRIAMINIC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
CONTAC COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF BROMANATE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF HYCOMINE
Common Name English
DRIZE COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF CODAMINE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE [USP-RS]
Common Name English
NSC-23798
Code 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
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF TAVIST-D
Common Name English
BROMATAPP COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
TAVIST-D COMPONENT PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF ORNADE
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
PHENYLPROPANOLAMINE HYDROCHLORIDE COMPONENT OF BIPHETAP
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C87053
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
205-826-7
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
DRUG BANK
DBSALT000996
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
NCI_THESAURUS
C66379
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
DAILYMED
8D5I63UE1Q
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
CAS
154-41-6
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL61006
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
PUBCHEM
62943
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
RXCUI
3266
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m8687
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY Merck Index
FDA UNII
8D5I63UE1Q
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
EVMPD
SUB14842MIG
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
SMS_ID
100000091354
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
RS_ITEM_NUM
1534005
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID2025896
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
NSC
23798
Created by admin on Fri Dec 15 16:21:18 GMT 2023 , Edited by admin on Fri Dec 15 16:21:18 GMT 2023
PRIMARY
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