Trolamine

Identification

Name
Trolamine
Accession Number
DB13747
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • 2,2',2''-nitrilotris(ethanol)
  • nitrilo-2,2',2''-triethanol
  • nitrilotriethanol
  • triethanolamine
  • tris(2-hydroxyethyl)amine
  • tris(β-hydroxyethyl)amine
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Tru-micinLotion0.1 mg/1mLTopicalTruceuticals, Llc2013-06-07Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bee Pollen-jojoba High Moisture CreamTrolamine (0.6 %) + Octinoxate (7.5 %) + Oxybenzone (3.0 %) + Titanium dioxide (0.1 %)CreamTopicalRachel Perry Inc.Not applicableNot applicableCanada
Calenda-cucumber Oil-free MoisturizerTrolamine (0.6 %) + Octinoxate (7.5 %) + Oxybenzone (3 %)CreamTopicalRachel Perry Inc.Not applicableNot applicableCanada
Lecithin-aloe Moisture CreamTrolamine (0.8 %) + Octinoxate (7.5 %) + Oxybenzone (4 %) + Titanium dioxide (0.15 %)CreamTopicalRachel Perry Inc.Not applicableNot applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Sallys Box Friendly Black Head Three Step SheetTrolamine (0.036 mg/3mL)CreamTopicalImine Co., Ltd.2015-01-052015-01-05Us
Categories
UNII
9O3K93S3TK
CAS number
102-71-6
Weight
Average: 149.1882
Monoisotopic: 149.105193351
Chemical Formula
C6H15NO3
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

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.

Associated Conditions
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.

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
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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenAcetaminophen may decrease the excretion rate of Trolamine which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Trolamine which could result in a higher serum level.
AlprazolamAlprazolam may decrease the excretion rate of Trolamine which could result in a higher serum level.
AmilorideAmiloride may increase the excretion rate of Trolamine which could result in a lower serum level and potentially a reduction in efficacy.
AmlodipineAmlodipine may decrease the excretion rate of Trolamine which could result in a higher serum level.
AmoxicillinAmoxicillin may decrease the excretion rate of Trolamine which could result in a higher serum level.
AmphetamineAmphetamine may decrease the excretion rate of Trolamine which could result in a higher serum level.
AmpicillinAmpicillin may decrease the excretion rate of Trolamine which could result in a higher serum level.
AuranofinAuranofin may decrease the excretion rate of Trolamine which could result in a higher serum level.
BaclofenBaclofen may decrease the excretion rate of Trolamine which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:23696578]
External Links
Human Metabolome Database
HMDB0032538
KEGG Drug
D00215
KEGG Compound
C06771
PubChem Compound
7618
PubChem Substance
347829313
ChemSpider
13835630
ChEBI
28621
ChEMBL
CHEMBL446061
HET
211
Wikipedia
Triethanolamine
ATC Codes
D03AX12 — Trolamine
PDB Entries
2hmp / 3frl / 3h7c / 3rq0 / 3zuk / 5cix / 6cww
MSDS
Download (164 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Not Yet RecruitingSupportive CareNasopharyngeal Neoplasms / Radiodermatitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical
CreamTopical0.036 mg/3mL
LotionTopical0.1 mg/1mL
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)21.6Fiume 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)335.4Fiume 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 solubilityMiscibleFiume 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-1.59Fiume 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.
pKa7.76Fiume 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
PropertyValueSource
Water Solubility497.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.9ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)8.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.93 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity38.86 m3·mol-1ChemAxon
Polarizability16.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-03di-1970000000-1cdc1ba11e5a386f1352
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9800000000-98de38ceda39aaf45b22
GC-MS Spectrum - GC-MSGC-MSsplash10-03di-1970000000-1cdc1ba11e5a386f1352
Mass Spectrum (Electron Ionization)MSsplash10-066r-9400000000-4742c6b283ff3c63f5cf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-ca2aa12d755f3b370137
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-1900000000-2b587564dc84bdc0bc33
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01pa-9300000000-57766f4027077ecafb7e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-b274020e58b6ef8d982c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1900000000-c82995f1eed61c2b1729
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fdo-9300000000-db20818734acbebe5241
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-0c50692a60886d3a9842
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ue9-3900000000-2610bf9e1d6b422b2581
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-ad4771662a2213681b1c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-9000000000-3099cf0c685e5aa6736f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006w-9000000000-d387d0ee743aefe8efec
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ue9-4900000000-a63f8f03a9f4f6fe4fd5
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Tertiary aliphatic amine / Tertiary amine / 1,2-aminoalcohol / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tertiary amino compound, amino alcohol (CHEBI:28621)

Drug created on June 23, 2017 14:47 / Updated on August 02, 2018 06:57