PHENYLPROPANOLAMINE, (-)-

US Previously Marketed

First approved in 1941

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 Search

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
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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.	2015-01	24792324
Khat use and neurobehavioral functions: suggestions for future studies.	2010-12-01	20553832
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).	2010-07-15	20632793
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.	2010-05	20497930
Ephedra alkaloids inhibit platelet aggregation.	2010-04	20179577
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.	2010-03	19637377
Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation.	2009-06-05	19446762
Comparison of fesoterodine and tolterodine in patients with overactive bladder.	2008-11	18647298
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.	2008-11	18510659
How many drugs for LUTS due to BPH are too many?	2008-09	18635235
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.	2008-05	18221372
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.	2007-08	17251912
Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones.	2007-04	17445639
Treatment of men with lower urinary tract symptoms and overactive bladder.	2007-03-21	17374810
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.	2006-12	17179687
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.	2006-09-12	16870379
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].	2006-07	16816976
Tolterodine.	2006-06-21	16784047
Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia.	2006-04	16618562
Using anticholinergics to treat overactive bladder: the issue of treatment tolerability.	2006-03	16483863
Juvenile pig detrusor: effects of propiverine and three of its metabolites.	2005-11-07	16256104
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.	2005-10-15	16154527
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.	2005-07	16161387
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Validation of the urgency perception scale.	2005-03	15705086
[Therapy of bladder weakness].	2005-01-21	15650964
Pharmacological management of overactive bladder : a systematic and critical review of published economic evaluations.	2005	16235973
Impact of a health education intervention in overactive bladder patients.	2004-12	15636668
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.	2004-09-03	15336373
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.	2004-07	15201268
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.	2004-02-06	14750795
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.	2003-08-21	12873745
Use of Ephedra-containing products and risk for hemorrhagic stroke.	2003-01-14	12525737
Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder.	2003-01	12614251
Adrenergic drugs for urinary incontinence in adults.	2003	12804414
Different responses to drugs against overactive bladder in detrusor muscle of pig, guinea pig and mouse.	2002-11-01	12409006
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.	2002-10	12324488
A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder.	2002-09	12175392
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.	2002-03-28	11922057
Don't be so quick to ban medications.	2002-01-08	11800236
Pharmacological properties of A-204176, a novel and selective alpha1A adrenergic agonist, in in vitro and in vivo models of urethral function.	2001-11-30	11787943
Tolterodine: an overview.	2001-11	11760779
Clarification--Drug risk in patients with glaucoma.	2001-06-11	11417565
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.	2001-03	11248608
Dystonic reaction following recommended use of a cold syrup.	1995-12	7492048
Phenylpropanolamine-induced psychosis. Potential predisposing factors.	1994-09	7995508
Alpha and beta adrenergic receptor involvement in catecholamine-induced growth of gram-negative bacteria.	1993-01-29	8381276
Nifedipine therapy of phenylpropanolamine-induced hypertension.	1987-02	3812201
Intracranial hemorrhages due to phenylpropanolamine.	1985-05-01	4002267

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 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

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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