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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-VXNVDRBHSA-N
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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Withdrawn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Withdrawn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
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Detrol LA and Diropan XL for overactive bladder.
2001 Apr 2
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
The effect of tolterodine on the pharmacokinetics and pharmacodynamics of a combination oral contraceptive containing ethinyl estradiol and levonorgestrel.
2001 Nov
Phenylpropanolamine appears not to promote weight loss in patients with schizophrenia who have gained weight during clozapine treatment.
2002 Apr
Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial.
2002 Oct
HPLC determination of phenylpropanolamine in pharmaceutical OTC preparations.
2002 Oct
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
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.
2004 Jul
Nocturnal enuresis in children. A four-year experience in outpatient clinics of pediatric urology.
2005
Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways.
2005 Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones.
2007 Apr
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
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.
2008 Jul-Aug
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
Transobturator vaginal tape inside out for treatment of urethral sphincter mechanism incompetence: preliminary results in 7 female dogs.
2010 Dec
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
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, (+)-
Common Name English
D-(+)-NOREPHEDRINE
Common Name English
BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, (.ALPHA.S)-
Systematic Name English
D-NOREPHEDRINE
Common Name English
(1R,2S)-2-HYDROXY-2-PHENYL-1-METHYL-1-AMINOETHANE
Systematic Name English
(1S,2R)-NOREPHEDRINE
Common Name English
D-PHENYLPROPANOLAMINE
Common Name English
(1S,2R)-2-AMINO-1-PHENYLPROPANOL
Common Name English
PHENYLPROPANOLAMINE, D-
Common Name English
(+)-PHENYLPROPANOLAMINE
Common Name English
(+)-(1S,2R)-NOREPHEDRINE
Common Name English
(1S,2R)-2-AMINO-1-PHENYLPROPAN-1-OL
Common Name English
(+)-NOREPHEDRINE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID301313960
Created by admin on Sat Dec 16 10:59:35 GMT 2023 , Edited by admin on Sat Dec 16 10:59:35 GMT 2023
PRIMARY
CAS
37577-28-9
Created by admin on Sat Dec 16 10:59:35 GMT 2023 , Edited by admin on Sat Dec 16 10:59:35 GMT 2023
PRIMARY
PUBCHEM
26934
Created by admin on Sat Dec 16 10:59:35 GMT 2023 , Edited by admin on Sat Dec 16 10:59:35 GMT 2023
PRIMARY
FDA UNII
7875H6443P
Created by admin on Sat Dec 16 10:59:35 GMT 2023 , Edited by admin on Sat Dec 16 10:59:35 GMT 2023
PRIMARY
NIH
NCATS
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