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

Details

Stereochemistry ACHIRAL
Molecular Formula C17H21NO.ClH
Molecular Weight 291.816
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLTOLOXAMINE HYDROCHLORIDE

SMILES

Cl.CN(C)CCOC1=C(CC2=CC=CC=C2)C=CC=C1

InChI

InChIKey=HMBOWANDONYIBI-UHFFFAOYSA-N
InChI=1S/C17H21NO.ClH/c1-18(2)12-13-19-17-11-7-6-10-16(17)14-15-8-4-3-5-9-15;/h3-11H,12-14H2,1-2H3;1H

HIDE SMILES / InChI
Molecular Formula C17H21NO
Molecular Weight 255.3547
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

Phenyltoloxamine is an ethanolamine derivative with antihistaminic property, which is used in combination with some analgesics for the temporary relief of minor aches and pains associated with headache; backache; muscular aches; temporarily reduces fever and some others disorders. Phenyltoloxamine blocks H1 histamine receptor, thereby inhibiting phospholipase A2 and production of endothelium-derived relaxing factor, nitric oxide. Subsequent lack of activation of guanylyl cyclase through nitric oxide results in decreased cyclic GMP levels, thereby inhibiting smooth muscle constriction of various tissues, decreasing capillary permeability and decreasing other histamine-activated allergic reactions.

Approval Year

1952
114
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
555
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Bristalin

Approved Use

Phenyltoloxamine is a first generation antihistamine that is used for symptoms of the common cold and as a short acting sedative.

Launch Date

1951
Primary
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Palliative
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Palliative
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Palliative
Not Provided
511
DOLOGESIC

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
60 mg single, oral
Recommended
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2569485/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2569485/
Sources:
https://pubmed.ncbi.nlm.nih.gov/2569485/
PubMed

PubMed

TitleDatePubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011-07-14
Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough.
2010-10-06
(2-Methyl-phen-yl)(phen-yl)methanol.
2010-07-31
Identification of potent chemotypes targeting Leishmania major using a high-throughput, low-stringency, computationally enhanced, small molecule screen.
2009-11-03
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009-10-02
Feasibility study of day case thyroidectomy.
2008-10
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.
2007-05
Ligand-based approach to in silico pharmacology: nuclear receptor profiling.
2006-11-28
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001-04
[Antimycobacterial antihistaminics].
1989-08
Patents

Patents

US3173835
3

Sample Use Guides

In Vivo Use Guide
adults and children 12 years of age and older: take 1 or 2 tablespoons of DOLOGESIC (acetaminophen, phenyltoloxamine citrate, alcohol liquid); every 4 to 6 hours. children under 12 years of age: Consult a physician; do not give this product to children under 12 years of age. This product will provide more than the recommended dose (overdose) of non-aspirin and could cause serious health problems
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:22:06 GMT 2025
Edited
by admin
on Mon Mar 31 18:22:06 GMT 2025
Record UNII
56O4H6ZT2K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-(2-DIMETHYLAMINOETHOXY)DIPHENYLMETHANE, HYDROCHLORIDE
Preferred Name English
PHENYLTOLOXAMINE HYDROCHLORIDE
MI  
Common Name English
N,N-DIMETHYL-2-(.ALPHA.-PHENYL-O-TOLYLOXY)ETHYLAMINE, HYDROCHLORIDE
Systematic Name English
PHENYLTOLOXAMINE HYDROCHLORIDE [MI]
Common Name English
N,N-DIMETHYL-2-(2-(PHENYLMETHYL)PHENOXY)ETHANAMINE, HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
Code System Code Type Description
MERCK INDEX
m8695
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY Merck Index
PUBCHEM
22528
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY
CAS
7587-47-5
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY
DRUG BANK
DBSALT002682
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY
MESH
C008865
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY
FDA UNII
56O4H6ZT2K
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY
NCI_THESAURUS
C97702
Created by admin on Mon Mar 31 18:22:06 GMT 2025 , Edited by admin on Mon Mar 31 18:22:06 GMT 2025
PRIMARY
Related Record Type Details
Structure of PHENYLTOLOXAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHENYLTOLOXAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966