PHENYLPROPANOLAMINE HYDROCHLORIDE, (+)-

US Previously Marketed

First approved in 1941

Details

Stereochemistry	ABSOLUTE
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, (+)-

Structure Search

SMILES

Cl.C[C@@H](N)[C@@H](O)C1=CC=CC=C1

InChI

InChIKey=DYWNLSQWJMTVGJ-PRCZDLBKSA-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-;/m1./s1

HIDE SMILES / InChI

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

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381276 | https://www.google.com/patents/US5260073http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihub
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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381276	Agonist 2752
Adrenergic receptor alpha 65 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 \| https://www.ncbi.nlm.nih.gov/pubmed/15608085	Agonist 2752
Alpha-1a adrenergic receptor 67 Target ID: CHEMBL319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918	Agonist 2752	9.8 µM [Ki]
Alpha-1b adrenergic receptor 45 Target ID: CHEMBL315 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918	Agonist 2752	280.0 µM [EC50]
Alpha-1d adrenergic receptor 37 Target ID: CHEMBL326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918	Agonist 2752	8.4 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Sinusitis 26 Sources: https://www.google.com/patents/US5260073	Primary	Not Provided 511	Unknown Approved Use Unknown
Otitis 38 Sources: https://www.google.com/patents/US5260073	Primary	Not Provided 511	Unknown Approved Use Unknown
Nasal congestion 27 Sources: https://www.drugs.com/dosage/phenylpropanolamine.html http://www.druginfosys.com/drug.aspx?drugcode=569&type=1	Primary	Withdrawn	PHENYLPROPANOLAMINE Approved Use Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Obesity 206 Sources: https://www.drugs.com/dosage/phenylpropanolamine.html http://www.druginfosys.com/drug.aspx?drugcode=569&type=1	Primary	Withdrawn	PHENYLPROPANOLAMINE Approved Use Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Nasal congestion 27 Sources: https://www.drugs.com/comments/phenylpropanolamine/	Primary	Withdrawn	CODAMINE Approved Use Unknown Launch Date 2000

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
ChemIDplus	67244900	https://chem.nlm.nih.gov/chemidplus/id/0067244900
PubChem	118984428	https://pubchem.ncbi.nlm.nih.gov/compound/118984428
Wikidata	Q27274344

PubMed

Title	Date	PubMed
Positive phentolamine test in hypertension induced by a nasal decongestant.	1969 Apr 17	4180300
Intracranial hemorrhages due to phenylpropanolamine.	1985 May-Jun	4002267
Alpha and beta adrenergic receptor involvement in catecholamine-induced growth of gram-negative bacteria.	1993 Jan 29	8381276
Phenylpropanolamine-induced psychosis. Potential predisposing factors.	1994 Sep	7995508
Dystonic reaction following recommended use of a cold syrup.	1995 Dec	7492048
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.	2001 Mar	11248608
Tolterodine: an overview.	2001 Nov	11760779
The effect of tolterodine on the pharmacokinetics and pharmacodynamics of a combination oral contraceptive containing ethinyl estradiol and levonorgestrel.	2001 Nov	11768839
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	11787943
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.	2001 Oct-Dec	11793881
Don't be so quick to ban medications.	2002 Jan 8	11800236
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.	2003 Aug 21	12873745
Use of Ephedra-containing products and risk for hemorrhagic stroke.	2003 Jan 14	12525737
Quantifying errors without random sampling.	2003 Jun 12	12892568
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.	2004 Feb 6	14750795
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.	2004 Jul	15201268
Effects of solifenacin succinate (YM905) on detrusor overactivity in conscious cerebral infarcted rats.	2005 Apr 4	15814091
Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways.	2005 Feb	15708029
[Therapy of bladder weakness].	2005 Jan 21	15650964
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.	2005 Jul	16161387
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Validation of the urgency perception scale.	2005 Mar	15705086
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.	2005 Oct 15	16154527
Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia.	2006 Apr	16618562
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.	2006 Dec	17179687
Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.	2006 Jun	16805764
Efficacy and tolerability of tolterodine extended-release in men with overactive bladder and urgency urinary incontinence.	2006 May	16643482
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.	2006 Sep 12	16870379
[Stroke and phenylpropanolamine: what risk factors and what recommendations in request?].	2007	19102094
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.	2007 Aug	17251912
Effect of tolterodine on sleep structure modulated by CYP2D6 genotype.	2008 Jul	17921051
Cost-effectiveness analysis of solifenacin flexible dosing in patients with overactive bladder symptoms in four Nordic countries.	2009	19384673
Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation.	2009 Jun 5	19446762
Ephedra alkaloids inhibit platelet aggregation.	2010 Apr	20179577
Mean arterial pressure: therapeutic goals and pharmacologic support.	2010 Apr	20381720
Khat use and neurobehavioral functions: suggestions for future studies.	2010 Dec 1	20553832
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.	2010 Feb 25	20047807
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).	2010 Jul 15	20632793
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.	2015 Jan	24792324

Patents

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

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:33:38 GMT 2025` Edited by `admin` on `Mon Mar 31 23:33:38 GMT 2025`
Record UNII	184M412SJH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENYLPROPANOLAMINE HYDROCHLORIDE, (+)-

Common Name

English

(+)-NOREPHEDRINE HYDROCHLORIDE

Preferred Name

English

D-PHENYLPROPANOLAMINE HYDROCHLORIDE

Common Name

English

PHENYLPROPANOLAMINE (+)-FORM HYDROCHLORIDE [MI]

Common Name

English

(1S,2R)-NOREPHEDRINE HYDROCHLORIDE

Common Name

English

(+)-PHENYLPROPANOLAMINE HYDROCHLORIDE

Common Name

English

(1S,2R)-(+)-NOREPHEDRINE HYDROCHLORIDE

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, HYDROCHLORIDE (1:1), (.ALPHA.S)-

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m8687