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Details

Stereochemistry ABSOLUTE
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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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Withdrawn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
Positive phentolamine test in hypertension induced by a nasal decongestant.
1969 Apr 17
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Dystonic reaction following recommended use of a cold syrup.
1995 Dec
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.
2001 Jun
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
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
A possible trend suggesting increased abuse from Coricidin exposures reported to the Texas Poison Network: comparing 1998 to 1999.
2002 Jun
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
Cerebral infarcts in a pediatric patient secondary to phenylpropanolamine, a recalled medication.
2004 Apr
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
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004 Sep 3
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
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.
2006 Dec
Tolterodine.
2006 Jun 6-12
Efficacy and tolerability of tolterodine extended-release in men with overactive bladder and urgency urinary incontinence.
2006 May
Effect of tolterodine on sleep structure modulated by CYP2D6 genotype.
2008 Jul
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.
2008 Jul-Aug
How many drugs for LUTS due to BPH are too many?
2008 Sep
Ephedra alkaloids inhibit platelet aggregation.
2010 Apr
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
Transobturator vaginal tape inside out for treatment of urethral sphincter mechanism incompetence: preliminary results in 7 female dogs.
2010 Dec
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.
2010 May
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 22:33:30 GMT 2025
Edited
by admin
on Mon Mar 31 22:33:30 GMT 2025
Record UNII
57B9YG5Y1E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLPROPANOLAMINE, (-)-
Common Name English
NSC-17704
Preferred Name English
(-)-NOREPHEDRIN
Common Name English
(1R,2S)-2-AMINO-1-PHENYL-1-PROPANOL
Systematic Name English
(-)-ERYTHRO-2-AMINO-2-METHYL-1-PHENYLETHANOL
Common Name English
NOREPHEDRINE, (-)-
Common Name English
PHENYLPROPANOLAMINE, L-
Common Name English
BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-, (.ALPHA.R)-
Systematic Name English
ERYTHRO-(1R,2S)-NOREPHEDRINE
Common Name English
(1R,2S)-(-)-NOREPHEDRINE
Common Name English
L-NOREPHEDRINE
Common Name English
(-)-PHENYLPROPANOLAMINE
Common Name English
(1S,2R)-2-HYDROXY-2-PHENYL-1-METHYL-1-AMINOETHANE
Systematic Name English
Code System Code Type Description
NSC
17704
Created by admin on Mon Mar 31 22:33:30 GMT 2025 , Edited by admin on Mon Mar 31 22:33:30 GMT 2025
PRIMARY
CAS
492-41-1
Created by admin on Mon Mar 31 22:33:30 GMT 2025 , Edited by admin on Mon Mar 31 22:33:30 GMT 2025
PRIMARY
FDA UNII
57B9YG5Y1E
Created by admin on Mon Mar 31 22:33:30 GMT 2025 , Edited by admin on Mon Mar 31 22:33:30 GMT 2025
PRIMARY
PUBCHEM
10297
Created by admin on Mon Mar 31 22:33:30 GMT 2025 , Edited by admin on Mon Mar 31 22:33:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID10889348
Created by admin on Mon Mar 31 22:33:30 GMT 2025 , Edited by admin on Mon Mar 31 22:33:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-755-7
Created by admin on Mon Mar 31 22:33:30 GMT 2025 , Edited by admin on Mon Mar 31 22:33:30 GMT 2025
PRIMARY
Related Record Type Details
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE, (-)-
SALT/SOLVATE -> PARENT
Structure of PHENYLPROPANOLAMINE
RACEMATE -> ENANTIOMER
Structure of PHENYLPROPANOLAMINE, (+)-
ENANTIOMER -> ENANTIOMER
NIH
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