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

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 is an enantiomer of propanolamine. The substance has low adrenergic activity and exerts measurable physiological effect only at high doses, which were lethal to experimental animals tested. 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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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

9.700992E11
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
Positive phentolamine test in hypertension induced by a nasal decongestant.
1969 Apr 17
Phenylpropanolamine-associated headache.
1985 Apr
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Intracerebral hemorrhage and phenylpropanolamine use.
1987 Mar
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
Phenylpropanolamine appears not to promote weight loss in patients with schizophrenia who have gained weight during clozapine treatment.
2002 Apr
A possible trend suggesting increased abuse from Coricidin exposures reported to the Texas Poison Network: comparing 1998 to 1999.
2002 Jun
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
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
Quantifying errors without random sampling.
2003 Jun 12
Implementation of the Methamphetamine Anti-Proliferation Act; thresholds for retailers and for distributors required to submit mail order reports; changes to mail order reporting requirements. Final rule.
2003 Oct 7
Cerebral infarcts in a pediatric patient secondary to phenylpropanolamine, a recalled medication.
2004 Apr
Impact of a health education intervention in overactive bladder patients.
2004 Dec
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
Effects of solifenacin succinate (YM905) on detrusor overactivity in conscious cerebral infarcted rats.
2005 Apr 4
Should we switch over to tolterodine in every child with non-neurogenic daytime urinary incontinence in whom oxybutynin failed?
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
Medical costs after initiation of drug treatment for overactive bladder: effects of selection bias on cost estimates.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Determination of ephedrine and related compounds in pharmaceutical preparations by ion chromatography with direct conductivity detection.
2005 May
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
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006 Jul
Relationships among symptoms, bother, and treatment satisfaction in overactive bladder patients.
2007
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007 Aug
Mixed urinary incontinence: continuing to confound?
2007 Dec
Effect of tolterodine on sleep structure modulated by CYP2D6 genotype.
2008 Jul
Effects of serum PSA on efficacy of tolterodine extended release with or without tamsulosin in men with LUTS, including OAB.
2008 Nov
Cost-effectiveness analysis of solifenacin flexible dosing in patients with overactive bladder symptoms in four Nordic countries.
2009
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
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
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
Patents

Sample Use Guides

Usual Adult Dose for Nasal Congestion 25 mg orally every 4 hours. -or- 75 mg orally extended release every 12 hours. Not to exceed 150 mg/day. Usual Adult Dose for Weight Loss 25 mg orally 3 times a day, one-half hour before meals. -or- 75 mg orally extended release once a day in the morning. The use of phenylpropanolamine for weight loss should be limited to 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 14:41:33 UTC 2023
Edited
by admin
on Thu Jul 06 14:41:33 UTC 2023
Record UNII
57B9YG5Y1E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLPROPANOLAMINE, (-)-
Common 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
NSC-17704
Code 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 Thu Jul 06 14:41:33 UTC 2023 , Edited by admin on Thu Jul 06 14:41:33 UTC 2023
PRIMARY
CAS
492-41-1
Created by admin on Thu Jul 06 14:41:33 UTC 2023 , Edited by admin on Thu Jul 06 14:41:33 UTC 2023
PRIMARY
FDA UNII
57B9YG5Y1E
Created by admin on Thu Jul 06 14:41:33 UTC 2023 , Edited by admin on Thu Jul 06 14:41:33 UTC 2023
PRIMARY
PUBCHEM
10297
Created by admin on Thu Jul 06 14:41:33 UTC 2023 , Edited by admin on Thu Jul 06 14:41:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID10889348
Created by admin on Thu Jul 06 14:41:33 UTC 2023 , Edited by admin on Thu Jul 06 14:41:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-755-7
Created by admin on Thu Jul 06 14:41:33 UTC 2023 , Edited by admin on Thu Jul 06 14:41:33 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
ENANTIOMER -> ENANTIOMER