Trolamine

US Previously Marketed

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 Search

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
Sources: https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=TROLAMINE&audience=professional;
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

Condition	Modality	Targets	Highest Phase	Product
Sunburns 22 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a8276be2-93f1-4782-b206-93ea31036216	Inactive ingredient		Approved 8583	Volu-Firm Approved Use Unknown
Impacted cerumen 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/11340s16lbl.pdf	Palliative		Withdrawn	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf	unhealthy, 21.6–84.9 Health Status: unhealthy Age Group: 21.6–84.9 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf	Disc. AE: Application site erythema... AEs leading to discontinuation/dose reduction: Application site erythema (6.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf	unhealthy, 21.6–84.9 Health Status: unhealthy Age Group: 21.6–84.9 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B4-0536	http://www.3bsc.com/index/pro_info.php?id=18384
3B Scientific (Wuhan) Corp	3B4-0537	http://www.3bsc.com/index/pro_info.php?id=18385
3B Scientific (Wuhan) Corp	3B4-0538	http://www.3bsc.com/index/pro_info.php?id=18386
3B Scientific (Wuhan) Corp	3B4-2977	http://www.3bsc.com/index/pro_info.php?id=77610
AA Blocks	AA003UYI	http://www.aablocks.com/goods/Goods/detail?id=AA003UYI
abcr GmbH	AB174244	http://www.abcr.com/shop/en/AB174244
abcr GmbH	AB354582	http://www.abcr.de/shop/en/AB354582
abcr GmbH	AB354583	http://www.abcr.com/shop/en/AB354583
abcr GmbH	AB354584	http://www.abcr.de/shop/en/AB354584
abcr GmbH	AB354585	http://www.abcr.de/shop/en/AB354585
Acadechem	ACDS-032071	http://www.acadechemical.com/product/106770
Achemica	ACMC-20ajek	http://www.achemica.com/prodinfo/?id=138096
Achemtek	0102-022738	http://www.achemtek.com/102-71-6
Acros Organics	AC139560025	https://www.fishersci.com/shop/products/triethanolamine-97-acros-organics/AC139560025
Acros Organics	AC421630025	https://www.fishersci.com/shop/products/triethanolamine-99-acros-organics-1/AC421630025
Acros Organics	AC421630250	https://www.fishersci.com/shop/products/triethanolamine-99-acros-organics/AC421630250
Alfa Aesar	L04486	https://www.alfa.com/en/catalog/L04486/
Alichem	490012088	http://www.alichem.com/en/products/102-71-6.html
Angene	AGN-PC-0DAJHK	http://www.angenechemical.com/productshow/AGN-PC-0DAJHK.html
Aurora Fine Chemicals LLC	A00.157.464	http://online.aurorafinechemicals.com/info?ID=A00.157.464
Aurora Fine Chemicals LLC	K02.098.739	http://online.aurorafinechemicals.com/info?ID=K02.098.739
Avantor Inc	101224-568	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101224-568
Avantor Inc	BT128875-100G	https://us.vwr.com/store/product/16637307/triethanolamine-trolamine-98
Avantor Inc	BT128875-2.5KG	https://us.vwr.com/store/product/16637307/triethanolamine-trolamine-98
Avantor Inc	BT128875-500G	https://us.vwr.com/store/product/16637307/triethanolamine-trolamine-98
Avantor Inc	JT9468-1	https://us.vwr.com/store/product/4563060/triethanolamine-trolamine-99-0-by-gc-baker-analyzed-j-t-baker
BioSynth	J-525067	https://www.biosynth.com/en/products/all-products/products/J-525067.html
BOC Sciences	73205-32-0	https://www.bocsci.com/triethanolamine-d15-cas-73205-32-0-item-307498.html
BroadPharm	BP-21029	https://www.broadpharm.com/web/product.php?catalog=BP-21029
Chem Scene	CS-5859	http://www.chemscene.com/102-71-6.html
Chemenu	CM116573	http://www.chemenu.com/products/CM116573
Chemspace	CSSS00000210588	https://chem-space.com/CSSS00000210588
Clearsynth	CS-EB-02183	https://www.clearsynth.com/en/CSEB02183.html
Clearsynth	CS-ER-02175	https://www.clearsynth.com/en/CSER02175.html
Fisher Chemical	T3504	https://www.fishersci.com/shop/products/triethanolamine-nf-fisher-chemical-2/p-203483
Fisher Chemical	T350500	https://www.fishersci.com/shop/products/triethanolamine-nf-fisher-chemical-2/p-203483
Fisher Chemical	T4071	https://www.fishersci.com/shop/products/triethanolamine-certified-fisher-chemical-3/p-203471
Fisher Chemical	T4074	https://www.fishersci.com/shop/products/triethanolamine-certified-fisher-chemical-3/p-203471
Fisher Chemical	T407500	https://www.fishersci.com/shop/products/triethanolamine-certified-fisher-chemical-3/p-203471
Glentham Life Sciences	GE0563	http://www.glentham.com/products/product/GE0563/
Hairui	HR123823	http://www.hairuichem.com/en/product/102-71-6.html
iChemical	EBD2205814	http://www.ichemical.com/products/102-71-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
LGC Standards	DRE-C17831900	https://www.lgcstandards.com/US/en/p/DRE-C17831900
LGC Standards	MM1204.00	https://www.lgcstandards.com/US/en/p/MM1204.00
Matrix Scientific	99578	https://www.matrixscientific.com/099578.html
mcule	MCULE-1846755153	https://mcule.com/MCULE-1846755153/
MedChem Express	HY-B1809	https://www.medchemexpress.com/Triethanolamine.html
MuseChem	I000173	https://www.musechem.com/product/I000173.html
Oakwood	242387	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=123386&ExtHyperLink=1
Otava	2828994	https://search.otavachemicals.com/#!/search?query=2828994&type=code&base=dbb
Parchem	17809	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-99-Reagent-Grade-007809.aspx
Parchem	25862	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-015862.aspx
Parchem	37993	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-85--027993.aspx
Parchem	37994	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-99--027994.aspx
Renno Tech	RP21273	http://www.rennotech.com/product_show.asp?id=26993
Sigma-Aldrich	16303_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/16303?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1696958_USP	https://www.sigmaaldrich.com/catalog/product/usp/1696958?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30-4160_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/304160?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30-4170_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/304170?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	33729_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/33729?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S016414	http://www.sinfoobiotech.com/product/1019812
Smolecule	S772719	https://www.smolecule.com/products/s772719
Synthetic Heterocycles	ADAL1017515	http://www.synhet.com/products/ADAL1017515
THE BioTek	bt-253452	https://www.thebiotek.com/product/inhibitors/bt-253452
Vitas-M Laboratory	STL264185	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL264185&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL144787	https://www.vladachem.com/product.php?products=102-71-6
VladaChem	VL160744	https://www.vladachem.com/product.php?products=102-71-6
VladaChem	VL165654	https://www.vladachem.com/product.php?products=102-71-6
Yuhao Chemical	LQ0371	http://www.chemyuhao.com/102-71-6.html

PubMed

Title	Date	PubMed
Effect of cationic micellar aggregates on the kinetics of oxidation of aminoalcohols by N-bromosuccinimide in alkaline medium.	2005-05-15	15837498
Photoreduction behavior of cytochrome c by zinc porphyrin in lipid media.	2005-05-13	15878113
Co phytoavailability for tomato in amended calcareous soils.	2005-04	15588767
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.	2005-03	15835735
A factor analysis for complex systems containing nimesulide.	2005-03	15666295
Frequent loss of RUNX3 gene expression in remnant stomach cancer and adjacent mucosa with special reference to topography.	2005-02-14	15685235
New structural motifs in manganese single-molecule magnetism from the use of triethanolamine ligands.	2005-01-28	15624221
Generation of human antibody fragments against Streptococcus mutans using a phage display chain shuffling approach.	2005-01-25	15667665
Polycationic dendrimers interact with RNA molecules: polyamine dendrimers inhibit the catalytic activity of Candida ribozymes.	2005-01-21	15645021
Complete charge pooling is prevented in viologen-based dendrimers by self-protection.	2004-12-03	15532019
[The problem and improvement of colorimetric method for determination of sulfite in foods containing sulfur compounds].	2004-12	15794092
A high-nuclearity "Celtic-ring" isopolyoxotungstate, [H12W36O120]12-, that captures trace potassium ions.	2004-11-03	15506722
Titanatranes derailed: static and dynamic triethanolamine slippage induced by polyphenoxide chelation.	2004-11-01	15500337
Efficient photocurrent generation by self-assembled monolayers composed of 3 10-helical peptides carrying linearly spaced naphthyl groups at the side chains.	2004-10-13	15469265
Determination of volatile corrosion inhibitors by capillary electrophoresis.	2004-10-08	15532588
Photosensitized hydrogen evolution from water using conjugated polymers wrapped in dendrimeric electrolytes.	2004-09-29	15382943
Photopolymerization of poly(ethylene glycol) diacrylate on eosin-functionalized surfaces.	2004-09-28	15379488
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).	2004-09-20	15360233
Patch test results with the metalworking fluid series of the German Contact Dermatitis Research Group (DKG).	2004-09	15479200
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.	2004-09	15338092
Triethanolamine zinc phosphite, (C6H13NO3)Zn2(HPO3): a templated network or a network of clusters?	2004-07-26	15257583
Quantitation of biomarkers of exposure to nitrogen mustards in urine from rats dosed with nitrogen mustards and from an unexposed human population.	2004-07-09	15239850
Rheological characterization of topical carbomer gels neutralized to different pH.	2004-07	15290859
Lactic acid production with lactate dehydrogenase using the visible light sensitization of zinc porphyrin.	2004-07	15239004
Alternative approach to enhancing cation selectivity in ion chromatography.	2004-06-11	15250413
Integrative analysis of the mitochondrial proteome in yeast.	2004-06	15208715
Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice.	2004-06	15056812
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.	2004-05-04	15150627
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].	2004-05	15218738
NTP toxicology and carcinogenesis studies of triethanolamine (Cas No. 102-71-6) in B6C3F1 mice (dermal studies).	2004-05	15213765
Phase III randomized trial of Calendula officinalis compared with trolamine for the prevention of acute dermatitis during irradiation for breast cancer.	2004-04-15	15084618
Synthesis, structure and magnetism of new single molecule magnets composed of MnII2MnIII2 alkoxo-carboxylate bridged clusters capped by triethanolamine ligands.	2004-04-07	15252679
Cubic phase prepared in an anionic/amphoteric surfactant/oleic acid/decane/water system and the relationship with the neighboring phase.	2004-03-30	15835130
Mixture additives inhibit the dermal permeation of the fatty acid, ricinoleic acid.	2004-02-28	14700524
Analysis of Tamm-Horsfall protein by high-performance liquid chromatography with native fluorescence.	2004-02-20	14971498
Mechanical and water barrier properties of glutenin films influenced by storage time.	2004-01-14	14709016
On-line collection/concentration and detection of sulfur dioxide in air by flow-injection spectrophotometry coupled with a chromatomembrane cell.	2004-01	14753267
Evaluation of method of preparation of passive diffusion tubes for measurement of ambient nitrogen dioxide.	2004-01	14737464
Physicochemical and crystallographic characterization of mefenamic acid complexes with alkanolamines.	2004-01	14648644
Carbopols as factors buffering triethanolamine interacting with artificial skin sebum.	2004	15850295
Effect of some anionic polymers on pH of triethanolamine aqueous solutions.	2004	15497608
Determination of alkanolamines in cattails (Typha latifolia) utilizing electrospray ionization with selected reaction monitoring and ion-exchange chromatography.	2004	15282789
Dynamic localization of SPE-9 in sperm: a protein required for sperm-oocyte interactions in Caenorhabditis elegans.	2003-12-03	14653860
A comparative study between catalase gene therapy and the cardioprotector monohydroxyethylrutoside (MonoHER) in protecting against doxorubicin-induced cardiotoxicity in vitro.	2003-12-01	14647150
The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-beta-cyclodextrin.	2003-11	14592694
Extracting material parameters from x-ray attenuation: a CT feasibility study using kilovoltage synchrotron x-rays incident upon low atomic number absorbers.	2003-10-21	14620065
Molecular energy and electron transfer assemblies made of self-organized lipid-porphyrin bilayer vesicles.	2003-10-06	14566867
Reactivity with Tris(hydroxymethyl)aminomethane confounds immunodetection of acrolein-adducted proteins.	2003-10	14565760
Photovoltaic properties of self-assembled monolayers of porphyrins and porphyrin-fullerene dyads on ITO and gold surfaces.	2003-07-30	15369370
Physicochemical determinants of linear alkylbenzene sulfonate (LAS) disposition in skin exposed to aqueous cutting fluid mixtures.	2002-06	14653312

Patents

Sample Use Guides

In Vivo Use Guide

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)

In Vitro Use Guide

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

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Name

Type

Language

TRIETHANOLAMINE

Preferred Name

English

Trolamine

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