Identification
- Brand Names
- Tru-micin
- Generic Name
- Trolamine
- DrugBank Accession Number
- DB13747
- Background
Trolamine, which is also referred to as triethanolamine (TEA), is a tertiary amine and a triol. It is a bifunctional compound that exhibits both properties of alcohols and amines. Trolamine contains small amounts of diethanolamine and ethanolamine and may also act as an antioxidant against the auto-oxidation of animal and vegetable fats 1. It is commonly used as a pH adjuster and surfactant in industrial and cosmetic products such as skin and hair conditioning products.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Trolamine (DB13747)
- Weight
- Average: 149.1882
Monoisotopic: 149.105193351 - Chemical Formula
- C6H15NO3
- Synonyms
- 2,2',2''-nitrilotris(ethanol)
- nitrilo-2,2',2''-triethanol
- nitrilotriethanol
- triethanolamine
- tris(2-hydroxyethyl)amine
- tris(β-hydroxyethyl)amine
- Trolamine
Pharmacology
- Indication
Trolamine is used as an alkalizing agent, surfactant, and counter-ion in cosmetic and pharmaceutical formulations 1. It is not considered to be an active pharmacological ingredient and so has no official indication.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Acts as a surfactant or alkalizing agent to aid in emulsification and solubilizing of compounds or in raising the pH of a solution 1
- Mechanism of action
As an amine, trolamine is capable of accepting a hydrogen to form hydroxide and a conjugate acid. This raises the pH of the solution. As a surfactant, it can lower the interfacial tension in a mixture or solution to prevent separation of emulsions or precipitation of a compound out of solution.
- Absorption
Dermal absorption of trolamine increases with the dose 1. This has been found to range from 19-28% in rats with doses of 68-276 mg/kg in 190 μL of acetone without occlusion and from 60-80% in mice with doses of 79-1120 mg/kg in the same volume of acetone.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Trolamine is excreted mostly as the unchanged compound 1. No diethanolamine or ethanolamine has been found. Very small amounts of trolamine glucuronide have been detected but not quantified.
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- Route of elimination
When orally administered to rats, the 53% of the trolamine dose was found to be excreted in the urine and 20% in the feces 1. 98% was excreted in the urine with intravenous administration.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Trolamine produced mild erythema and edema in rabbits with dermally administered doses of 2 g/kg under occlusion 1. The oral LD50 was found to be 8 g/kg in guinea pigs and 4.19-11.26 g/kg in rats. Repeated oral administration in rats and guinea pigs produced hepatic and renal damage with deaths occurring in rats at doses >0.3 g/kg/day. When inhaled trolamine produced edema and inflammation in rats at doses over 100 mg/m³ after 5 days and at doses over 4.7 mg/m³ after 90 days. There is some evidence of carcinogenicity at high dermal doses (1000 mg/kg/day) in mice. Trolamine is not classified as a carcinogen in humans.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareTenofovir alafenamide The serum concentration of Tenofovir alafenamide can be increased when it is combined with Trolamine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Sallys Box Friendly Black Head Three Step Sheet Cream 0.036 mg/3mL Topical Imine Co., Ltd. 2015-01-05 2015-01-05 US 
Tru-micin Lotion 0.1 mg/1mL Topical Truceuticals, Llc 2013-06-07 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bee Pollen-jojoba High Moisture Cream Trolamine (0.6 %) + Octinoxate (7.5 %) + Oxybenzone (3.0 %) + Titanium dioxide (0.1 %) Cream Topical Rachel Perry Inc. Not applicable Not applicable Canada 
Calenda-cucumber Oil-free Moisturizer Trolamine (0.6 %) + Octinoxate (7.5 %) + Oxybenzone (3 %) Cream Topical Rachel Perry Inc. Not applicable Not applicable Canada Lecithin-aloe Moisture Cream Trolamine (0.8 %) + Octinoxate (7.5 %) + Oxybenzone (4 %) + Titanium dioxide (0.15 %) Cream Topical Rachel Perry Inc. Not applicable Not applicable Canada Protection Hp Hand Sanitizergel Trolamine (0.98 g/350mL) + Carbomer (1.05 g/350mL) + Ethanol (262.5 mL/350mL) Gel Extracorporeal Shenzhen Anmay Paper Manufacture Co., Ltd. 2020-05-20 Not applicable US Protection Hp Hand Sanitizergel Trolamine (1.4 g/500mL) + Carbomer (1.5 g/500mL) + Ethanol (375 mL/500mL) Gel Extracorporeal Shenzhen Anmay Paper Manufacture Co., Ltd. 2020-05-20 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Sallys Box Friendly Black Head Three Step Sheet Trolamine (0.036 mg/3mL) Cream Topical Imine Co., Ltd. 2015-01-05 2015-01-05 US
Categories
- ATC Codes
- D03AX12 — Trolamine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- 1,2-aminoalcohols
- Alternative Parents
- Trialkylamines / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 1,2-aminoalcohol / Alcohol / Aliphatic acyclic compound / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Tertiary aliphatic amine / Tertiary amine
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- tertiary amino compound, amino alcohol (CHEBI:28621)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9O3K93S3TK
- CAS number
- 102-71-6
- InChI Key
- GSEJCLTVZPLZKY-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2
- IUPAC Name
- 2-[bis(2-hydroxyethyl)amino]ethan-1-ol
- SMILES
- OCCN(CCO)CCO
References
- General References
- Fiume MM, Heldreth B, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler D, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Andersen FA: Safety assessment of triethanolamine and triethanolamine-containing ingredients as used in cosmetics. Int J Toxicol. 2013 May-Jun;32(3 Suppl):59S-83S. doi: 10.1177/1091581813488804. [Article]
- External Links
- Human Metabolome Database
- HMDB0032538
- KEGG Drug
- D00215
- KEGG Compound
- C06771
- PubChem Compound
- 7618
- PubChem Substance
- 347829313
- ChemSpider
- 13835630
- 38623
- ChEBI
- 28621
- ChEMBL
- CHEMBL446061
- ZINC
- ZINC000000896409
- PDBe Ligand
- 211
- Wikipedia
- Triethanolamine
- PDB Entries
- 2hmp / 3frl / 3h7c / 3rq0 / 3zuk / 5cix / 6cww
- MSDS
- Download (164 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Allergic Reaction 2 3 Completed Treatment Dermatitis, Photoallergic 1 3 Completed Treatment Dermatitis, Phototoxic 1 2 Unknown Status Supportive Care Nasopharyngeal Neoplasms / Radiodermatitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Gel Extracorporeal Liquid Extracorporeal Cream Topical 0.036 mg/3mL Liquid Topical Lotion Topical 0.1 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 21.6 Fiume MM, Heldreth B, Bergfeld WF, et al. Safety assessment of triethanolamine and triethanolamine-containing ingredients as used in cosmetics. Int J Toxicol. 2013;32(3 Suppl):59S-83S. boiling point (°C) 335.4 Fiume MM, Heldreth B, Bergfeld WF, et al. Safety assessment of triethanolamine and triethanolamine-containing ingredients as used in cosmetics. Int J Toxicol. 2013;32(3 Suppl):59S-83S. water solubility Miscible Fiume MM, Heldreth B, Bergfeld WF, et al. Safety assessment of triethanolamine and triethanolamine-containing ingredients as used in cosmetics. Int J Toxicol. 2013;32(3 Suppl):59S-83S. logP -1.59 Fiume MM, Heldreth B, Bergfeld WF, et al. Safety assessment of triethanolamine and triethanolamine-containing ingredients as used in cosmetics. Int J Toxicol. 2013;32(3 Suppl):59S-83S. pKa 7.76 Fiume MM, Heldreth B, Bergfeld WF, et al. Safety assessment of triethanolamine and triethanolamine-containing ingredients as used in cosmetics. Int J Toxicol. 2013;32(3 Suppl):59S-83S. - Predicted Properties
Property Value Source Water Solubility 497.0 mg/mL ALOGPS logP -1.4 ALOGPS logP -1.9 Chemaxon logS 0.52 ALOGPS pKa (Strongest Acidic) 15.12 Chemaxon pKa (Strongest Basic) 8.44 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 63.93 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 38.86 m3·mol-1 Chemaxon Polarizability 16.38 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.8948042 predictedDarkChem Lite v0.1.0 [M-H]- 130.7023042 predictedDarkChem Lite v0.1.0 [M-H]- 129.34485 predictedDeepCCS 1.0 (2019) [M+H]+ 127.9768042 predictedDarkChem Lite v0.1.0 [M+H]+ 128.0769042 predictedDarkChem Lite v0.1.0 [M+H]+ 132.27501 predictedDeepCCS 1.0 (2019) [M+Na]+ 128.3917042 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.4975042 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.06438 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:47 / Updated at September 28, 2021 21:54