U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C6H15NO3
Molecular Weight 149.1882
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Trolamine

SMILES

OCCN(CCO)CCO

InChI

InChIKey=GSEJCLTVZPLZKY-UHFFFAOYSA-N
InChI=1S/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2

HIDE SMILES / InChI

Molecular Formula C6H15NO3
Molecular Weight 149.1882
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 using several sources including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/11340s16lbl.pdf; https://www.ons.org/intervention/trolamine-biafine®; https://www.ncbi.nlm.nih.gov/pubmed/?term=15084618; https://clinicaltrials.gov/ct2/show/NCT02729324; http://www.ncbi.nlm.nih.gov/pubmed/18441842

Trolamine, an organic compound, is the salt formed between triethanolamine and salicylic acid. It is widely used as a topical analgesic. 10% trolamine salicylate medical products sold over-the-counter such as are creams for temporarily relief of minor aches and pains of muscles and joints associated with arthritis, simple backache, lumbago, neuralgia, strains, bruises, and sprains. The FDA approved in 1958 otic solution drops containing triethanolamine polypeptide used in the ear to break down and loosen earwax was discontinued. Trolamine can enhance skin healing by recruiting macrophages and modifying the concentrations of various immunomodulators. Trolamine (Biafine; Genmedix Ltd, France) is commonly prescribed at the beginning of radiotherapy for preventing acute radiation-induced skin toxicity in China. Biafine has been studied in radiodermatitis and Phase 2 clinical trial has been initiated in 2016 by Sun Yat-sen University to establish the efficacy of trolamine (Biafine) for the management of radiation dermatitis in patients with nasopharyngeal carcinoma receiving IMRT.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Volu-Firm

Approved Use

Unknown
Palliative
CERUMENEX

Approved Use

For removal of impacted cerumen prior to ear examination, otologic therapy and/or audiometry. CERUMENEX Eardrops should be used only with caution in external otitis.

Launch Date

1958
Doses

Doses

DosePopulationAdverse events​
5.38 mg 2 times / day multiple, topical
Studied dose
Dose: 5.38 mg, 2 times / day
Route: topical
Route: multiple
Dose: 5.38 mg, 2 times / day
Sources:
unhealthy, 21.6–84.9
Disc. AE: Application site erythema...
AEs leading to
discontinuation/dose reduction:
Application site erythema (6.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Application site erythema 6.7%
Disc. AE
5.38 mg 2 times / day multiple, topical
Studied dose
Dose: 5.38 mg, 2 times / day
Route: topical
Route: multiple
Dose: 5.38 mg, 2 times / day
Sources:
unhealthy, 21.6–84.9
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Fluorescent derivatization of nitrite ions with 2,3-diaminonaphthalene utilizing a pH gradient in a Y-shaped microchannel.
2001 Apr
Analysis of illicit amphetamine seizures by capillary zone electrophoresis.
2002 Dec 6
Quantitation of nicotine in tobacco products by capillary electrophoresis.
2002 Jan-Feb
Synthesis and characterization of mesoporous indium tin oxide possessing an electronically conductive framework.
2002 Jul 24
Amines compounds as inhibitors of PCDD/Fs de novo formation on sintering process fly ash.
2002 Jun 15
Photobleaching of a solid photochromic medium by a Gaussian laser beam.
2002 May 20
Assessing changes in Cd phytoavailability to tomato in amended calcareous soils.
2002 Oct
Sustaining pattern of phenformin hydrochloride using various polymers and waxes.
2002 Sep-Oct
Carcinostatic, protective, and adaptive activities of tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids.
2002 Sep-Oct
Coordination and fluorescence of the intracellular Zn2+ probe [2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxy]acetic acid (Zinquin A) in ternary Zn2+ complexes.
2003 Apr 2
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003 Apr 22
Enantiomeric separation of TAPP, H-Tyr-(D)Ala-Phe-Phe-NH(2), by capillary electrophoresis using 18-crown-6-tetracarboxylic acid as a chiral selector.
2003 Aug 15
The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid.
2003 Aug 27
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
2003 Feb
Expression and function of bradykinin receptors in microglia.
2003 Feb 21
Correlation between pK(a) and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope.
2003 Feb 7
Equilibria of mononuclear oxomolybdenum(VI) complexes of triethanolamine. A multinuclear dynamic magnetic resonance study of structure and exchange mechanisms.
2003 Jul
A novel two-pore domain K+ channel, TRESK, is localized in the spinal cord.
2003 Jul 25
Photovoltaic properties of self-assembled monolayers of porphyrins and porphyrin-fullerene dyads on ITO and gold surfaces.
2003 Jul 30
Capillary electrophoresis determinations of trace concentrations of inorganic ions in large excess of chloride: soft modelling using artificial neural networks for optimisation of electrolyte composition.
2003 Jun
Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum.
2003 Mar
Synthesis of uniform anatase TiO2 nanoparticles by gel-sol method. 4. Shape control.
2003 Mar 1
Synthesis of uniform anatase TiO2 nanoparticles by gel-sol method. 3. Formation process and size control.
2003 Mar 1
Substantial increase of the ordering temperature for [MnII/MoIII(CN)7]-based magnets as a function of the 3d ion site geometry: example of two supramolecular materials with Tc = 75 and 106 K.
2003 Mar 10
Identification of selenium species in urine by ion-pairing HPLC-ICP-MS using laboratory-synthesized standards.
2003 Oct
Direct and fast capillary zone electrophoretic method for the determination of Gleevec and its main metabolite in human urine.
2003 Sep 5
Carbopols as factors buffering triethanolamine interacting with artificial skin sebum.
2004
Effect of some anionic polymers on pH of triethanolamine aqueous solutions.
2004
Determination of alkanolamines in cattails (Typha latifolia) utilizing electrospray ionization with selected reaction monitoring and ion-exchange chromatography.
2004
Phase III randomized trial of Calendula officinalis compared with trolamine for the prevention of acute dermatitis during irradiation for breast cancer.
2004 Apr 15
Analysis of Tamm-Horsfall protein by high-performance liquid chromatography with native fluorescence.
2004 Feb 20
On-line collection/concentration and detection of sulfur dioxide in air by flow-injection spectrophotometry coupled with a chromatomembrane cell.
2004 Jan
Evaluation of method of preparation of passive diffusion tubes for measurement of ambient nitrogen dioxide.
2004 Jan
Rheological characterization of topical carbomer gels neutralized to different pH.
2004 Jul
Lactic acid production with lactate dehydrogenase using the visible light sensitization of zinc porphyrin.
2004 Jul
Integrative analysis of the mitochondrial proteome in yeast.
2004 Jun
Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice.
2004 Jun
Cubic phase prepared in an anionic/amphoteric surfactant/oleic acid/decane/water system and the relationship with the neighboring phase.
2004 Mar 30
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
NTP toxicology and carcinogenesis studies of triethanolamine (Cas No. 102-71-6) in B6C3F1 mice (dermal studies).
2004 May
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.
2004 May 4
Efficient photocurrent generation by self-assembled monolayers composed of 3 10-helical peptides carrying linearly spaced naphthyl groups at the side chains.
2004 Oct 13
Patch test results with the metalworking fluid series of the German Contact Dermatitis Research Group (DKG).
2004 Sep
Determination of diethanolamine or N-methyldiethanolamine in high ammonium concentration matrices by capillary electrophoresis with indirect UV detection: application to the analysis of refinery process waters.
2004 Sep
Functionalized metal oxide clusters: synthesis, characterization, crystal structures, and magnetic properties of a novel series of fully reduced heteropolyoxovanadium cationic clusters decorated with organic ligands--[MVIV6O6[(OCH2CH2)2N(CH2CH2OH)]6]X (M = Li, X = Cl x LiCl; M = Na, X = Cl x H2O; M = Mg, X = 2Br x H2O; M = Mn, Fe, X = 2Cl; M = Co, Ni, X = 2Cl x H2O).
2004 Sep 20
Photopolymerization of poly(ethylene glycol) diacrylate on eosin-functionalized surfaces.
2004 Sep 28
Photosensitized hydrogen evolution from water using conjugated polymers wrapped in dendrimeric electrolytes.
2004 Sep 29
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.
2005 Mar
Photoreduction behavior of cytochrome c by zinc porphyrin in lipid media.
2005 May 13
Effect of cationic micellar aggregates on the kinetics of oxidation of aminoalcohols by N-bromosuccinimide in alkaline medium.
2005 May 15
Patents

Sample Use Guides

Fill ear canal with ear drops of 10% triethanolamine Polypeptide Oleate-Condensate with the patient’s head tilted at a 45° angle. Insert cotton plug and allow to remain 15-30 minutes. Then gently flush with lukewarm water, using a soft rubber syringe (avoid excessive pressure). Exposure of skin outside the ear to the drug should be avoided. The procedure may be repeated if the first application fails to clear the impaction.
Route of Administration: Otic (auricular)
Penetration of triethanolamine into artificial skin sebum and its uplift were measured using 0.1 M aqueous triethanolamine solution.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:17:35 GMT 2025
Edited
by admin
on Mon Mar 31 18:17:35 GMT 2025
Record UNII
9O3K93S3TK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIETHANOLAMINE
INCI   MI   VANDF  
INCI  
Preferred Name English
Trolamine
EP   HSDB   II   INN   MART.   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
TROLAMINE [MART.]
Common Name English
TROLAMINE [EP MONOGRAPH]
Common Name English
TRIETHANOLAMINE [VANDF]
Common Name English
TROLAMINE [II]
Common Name English
TROLAMINE [HSDB]
Common Name English
ETHANOL, 2,2',2''-NITRILOTRIS-
Systematic Name English
TROLAMINE [EP IMPURITY]
Common Name English
NSC-36718
Code English
Trolamine [WHO-DD]
Common Name English
TRIETHANOLAMINE [IARC]
Common Name English
TROLAMINE [VANDF]
Common Name English
TRIETHANOLAMINE [MI]
Common Name English
trolamine [INN]
Common Name English
2,2',2''-NITRILOTRIETHANOL
Systematic Name English
Classification Tree Code System Code
WHO-ATC D03AX12
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
EPA PESTICIDE CODE 4208
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2768
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL446061
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
MERCK INDEX
m11100
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
TRIETHANOLAMINE
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-049-8
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
INN
561
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
CHEBI
28621
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
CONCEPT Industrial Aid
EVMPD
SUB12376MIG
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
FDA UNII
9O3K93S3TK
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID9021392
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
RS_ITEM_NUM
1696958
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
RXCUI
38623
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB13747
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
SMS_ID
100000079034
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
NSC
36718
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
DAILYMED
9O3K93S3TK
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
MESH
C009546
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
PUBCHEM
7618
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
NCI_THESAURUS
C80948
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
CAS
102-71-6
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
HSDB
893
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
ACTIVE MOIETY