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 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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
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
[Cerebral hemorrhage associated with the use of phenylpropanolamine. Clinical cases].
1996 Dec
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.
2001 Jun
Clarification--Drug risk in patients with glaucoma.
2001 Jun 11
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
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
Effect of tolterodine on the anticoagulant actions and pharmacokinetics of single-dose warfarin in healthy volunteers.
2002
Phenylpropanolamine appears not to promote weight loss in patients with schizophrenia who have gained weight during clozapine treatment.
2002 Apr
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
A possible trend suggesting increased abuse from Coricidin exposures reported to the Texas Poison Network: comparing 1998 to 1999.
2002 Jun
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
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
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
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
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Validation of the urgency perception scale.
2005 Mar
Tolterodinium (+)-(2R,3R)-hydrogen tartrate.
2005 Mar
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
Use of oral decongestants during pregnancy and delivery outcome.
2006 Feb
[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 extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.
2006 Jun
Efficacy and tolerability of tolterodine extended-release in men with overactive bladder and urgency urinary incontinence.
2006 May
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.
2006 Sep 12
[Stroke and phenylpropanolamine: what risk factors and what recommendations in request?].
2007
Relationships among symptoms, bother, and treatment satisfaction in overactive bladder patients.
2007
The nonmedical use of prescription ADHD medications: results from a national Internet panel.
2007 Oct 31
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.
2008 Jul-Aug
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
Cost-effectiveness analysis of solifenacin flexible dosing in patients with overactive bladder symptoms in four Nordic countries.
2009
Keep an eye on the pupil: developing countries under chemical attack.
2009 Jun
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
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
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 Wed Jul 05 23:47:53 UTC 2023
Edited
by admin
on Wed Jul 05 23:47:53 UTC 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 Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
205-826-7
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
DRUG BANK
DBSALT000996
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
NCI_THESAURUS
C66379
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
DAILYMED
8D5I63UE1Q
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
CAS
154-41-6
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL61006
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
RXCUI
3266
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M8687
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY Merck Index
FDA UNII
8D5I63UE1Q
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
EVMPD
SUB14842MIG
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
SMS_ID
100000091354
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
RS_ITEM_NUM
1534005
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID2025896
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
NSC
23798
Created by admin on Wed Jul 05 23:47:53 UTC 2023 , Edited by admin on Wed Jul 05 23:47:53 UTC 2023
PRIMARY
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