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

Details

Stereochemistry ACHIRAL
Molecular Formula C2H7NO
Molecular Weight 61.0832
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOETHANOLAMINE

SMILES

C(CO)N

InChI

InChIKey=HZAXFHJVJLSVMW-UHFFFAOYSA-N
InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2

HIDE SMILES / InChI

Molecular Formula C2H7NO
Molecular Weight 61.0832
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Monoethanolamine is both a primary amine and a primary alcohol. It is an olamine derivative. Monoethanolamine occurs in every cell in the human body as the head group of Phosphatidylethanolamine. Monoethanolamine is a component of glycosylphosphatidylinositol-anchored proteins, which are essential for viability. Other sources of monoethanolamine or phosphoethanolamine in the human body are the degradation of sphingosine phosphate by sphingosine phosphate lyase and the degradation of the endocannabinoid anandamide by the fatty acid amine hydrolase. Monoethanolamine stimulates the rapid growth of mammalian cells in culture. Monoethanolamine has a cardioprotective role against ischemia/reperfusion injury via activation of the transcription factor STAT-3. Monoethanolamine is a chemical intermediate in the manufacture of cosmetics, surface-active agents, emulsifiers, pharmaceuticals, and plasticizing agents.

Originator

Sources: DOI: 10.1002/cber.189703001178

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Binding specificity of Bacillus thuringiensis Cry1Aa for purified, native Bombyx mori aminopeptidase N and cadherin-like receptors.
2001
The linkage between beta1 integrin and the actin cytoskeleton is differentially regulated by tyrosine and serine/threonine phosphorylation of beta1 integrin in normal and cancerous human breast cells.
2001
Structure-activity relationship studies of (+/-)-terbutaline and (+/-)-fenoterol on beta3-adrenoceptors in the guinea pig gastric fundus.
2001 Aug
Encephalitozoon cuniculi (Microspora): characterization of a phospholipid metabolic pathway potentially linked to therapeutics.
2001 Aug
Liquid ionization mass spectrometry of some triorganotin carboxylates.
2001 Dec
Control of autofluorescence of archival formaldehyde-fixed, paraffin-embedded tissue in confocal laser scanning microscopy (CLSM).
2001 Dec
Phosphatidylethanolamine has an essential role in Saccharomyces cerevisiae that is independent of its ability to form hexagonal phase structures.
2001 Dec 21
Beta 3 agonists. Part 1: evolution from inception to BMS-194449.
2001 Dec 3
[Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (Biovar I)].
2001 Jul-Aug
Toxicity of amiodarone and amiodarone analogues on isolated rat liver mitochondria.
2001 Nov
Nature of glycosylphosphatidylinositols produced by mouse embryonic stem cells.
2001 Nov
Confocal and probe microscopy to study gene transfection mediated by cationic liposomes with a cationic cholesterol derivative.
2001 Nov 19
Tissue-specific and developmental effects of the easily shocked mutation on ethanolamine kinase activity and phospholipid composition in Drosophila melanogaster.
2001 Oct
Decomposition of bisphenol-A (BPA) by radical oxygen.
2001 Oct
Polar nitrogen compounds and their behaviour in the drinking water treatment process.
2001 Oct
Synthesis and biopharmaceutical characterisation of new poly(hydroxyethylaspartamide) copolymers as drug carriers.
2001 Oct 3
Macromolecular prodrugs. IX. Synthesis of polymer-fenoprofen conjugates.
2001 Oct 9
Maternal-fetal n-6 and n-3 polyunsaturated fatty acids gradient in plasma and red cell phospholipids.
2001 Sep
Early ethanolamine phospholipid translocation marks stress-induced apoptotic cell death in oligodendroglial cells.
2001 Sep
Interaction of the substrate radical and the 5'-deoxyadenosine-5'-methyl group in vitamin B(12) coenzyme-dependent ethanolamine deaminase.
2001 Sep 5
Poly(amide ester)s from 2,6-pyridinedicarboxylic acid and ethanolamine derivatives: identification of macrocycles by matrix-assisted laser desorption/ionization mass spectrometry.
2002
[Structural and metabolic status and functional properties of erythrocytes in schizophrenic patients].
2002
Ethanolamine is a co-mitogenic factor for proliferation of primary hepatocytes.
2002
Thermal study of simple amino-alcohol solutions.
2002 Apr
Detection of ligands for selectins in the oligosaccharide fraction of human milk.
2002 Apr
Glycosylphosphatidylinositol (GPI)-anchored proteins.
2002 Apr
Mutations inducing divergent shifts of constitutive activity reveal different modes of binding among catecholamine analogues to the beta(2)-adrenergic receptor.
2002 Apr
Amiodarone-induced phospholipidosis: an in vivo [14C]-acetate uptake study in rat.
2002 Aug
Evaluation and optimization of DNA delivery into gliosarcoma 9L cells by a cholesterol-based cationic liposome.
2002 Aug 31
New structures of the O-specific polysaccharides of bacteria of the genus Proteus. 1. Phosphate-containing polysaccharides.
2002 Feb
Cytoskeletal inhibitors, anti-adhesion molecule antibodies, and lectins inhibit hepatocyte spheroid formation.
2002 Feb
Regulation of phosphatidylcholine and phosphatidylethanolamine synthesis in rat hepatocytes by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR).
2002 Feb 15
Kinetic analyses of liver phosphatidylcholine and phosphatidylethanolamine biosynthesis using (13)C NMR spectroscopy.
2002 Feb 28
Rapid synthesis and turnover of brain microsomal ether phospholipids in the adult rat.
2002 Jan
Dietary n-3 and n-6 fatty acids alter avian metabolism: molecular-species composition of breast-muscle phospholipids.
2002 Jul
Algicidal effectiveness of Clearigate, Cutrine-Plus, and copper sulfate and margins of safety associated with their use.
2002 Jul
Computational exploration of rearrangements related to the vitamin B12-dependent ethanolamine ammonia lyase catalyzed transformation.
2002 Jul 31
Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor.
2002 Jun
LC-MS/MS identification of in vitro metabolites of a new H+/K+ ATPase inhibitor, KR-60436 produced by rat and human liver microsomes.
2002 Jun 1
Comparative study of the effects of short- and long-term ethanol treatment and alcohol withdrawal on phospholipid biosynthesis in rat hepatocytes.
2002 Mar
Extracellular release of the glycosylphosphatidylinositol (GPI)-linked Leishmania surface metalloprotease, gp63, is independent of GPI phospholipolysis: implications for parasite virulence.
2002 Mar 15
Hydroxyethylamine isostere of an HIV-1 protease inhibitor prefers its amine to the hydroxy group in binding to catalytic aspartates. A synchrotron study of HIV-1 protease in complex with a peptidomimetic inhibitor.
2002 Mar 28
Behavior and characteristics of amine derivatives obtained with o-phthaldialdehyde/3-mercaptopropionic acid and with o-phthaldialdehyde/N-acetyl-L-cysteine reagents.
2002 Mar 8
Endometriosis in reproductive immunology.
2002 May
Phospholipid biosynthesis in the oyster protozoan parasite, Perkinsus marinus.
2002 May
Characterization of the hom-thrC-thrB cluster in aminoethoxyvinylglycine-producing Streptomyces sp. NRRL 5331.
2002 May
Stereochemical properties of lysophosphatidic acid receptor activation and metabolism.
2002 May 23
Structure-activity relationships of lysophosphatidic acid analogs.
2002 May 23
Phosphomonoester concentrations differ between chronic lymphocytic leukemia cells and normal human lymphocytes.
2002 Oct
Involvement of delta-aminolaevulinate synthase encoded by the parasite gene in de novo haem synthesis by Plasmodium falciparum.
2002 Oct 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Ethanolamine is a product of metabolism of sphingosine-1-phosphate (of S1P)
Rat: single injection 5 mg/kg of S1P
Route of Administration: Intravenous
1 uM of Monoethanolamine is required to activate virulence gene expression in Escherichia coli O157:H7 (EHEC), and this concentration is far below the concentration required for ethanolamine to be used as a nitrogen source.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:07:37 UTC 2021
Edited
by admin
on Fri Jun 25 21:07:37 UTC 2021
Record UNII
5KV86114PT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MONOETHANOLAMINE
II   USP-RS  
Systematic Name English
MONOETHANOLAMINE [II]
Common Name English
ETHANOLAMINE [WHO-DD]
Common Name English
ETHANOLAMINE
HSDB   INCI   MI   WHO-DD  
INCI  
Official Name English
MONOETHANOLAMINE [USP-RS]
Common Name English
OLAMINE [INN]
Common Name English
ETHANOLAMINE [EP MONOGRAPH]
Common Name English
2-AMINOETHANOL
Systematic Name English
TROLAMINE IMPURITY A [EP]
Common Name English
ETHANOLAMINE [HSDB]
Common Name English
ETHANOLAMINE [MI]
Common Name English
OLAMINE
INN  
INN  
Official Name English
ETHANOLAMINE [INCI]
Common Name English
Classification Tree Code System Code
LOINC 34300-4
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 28605-4
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 26608-0
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 56678-6
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 2264-0
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 13740-6
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
NDF-RT N0000175814
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
NDF-RT N0000009905
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 15137-3
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 26593-4
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 15142-3
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 25910-1
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
EPA PESTICIDE CODE 11601
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
NDF-RT N0000020024
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 49633-1
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 32239-6
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LOINC 25098-5
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NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 13613-5
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LOINC 6881-7
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LOINC 2263-2
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LOINC 25911-9
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
FDA ORPHAN DRUG 416713
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 25405-2
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
LOINC 26803-7
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
Code System Code Type Description
EPA CompTox
141-43-5
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
MESH
D019856
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
USP_CATALOG
1445925
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY USP-RS
PUBCHEM
700
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
RXCUI
24457
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61756
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
EVMPD
SUB01990MIG
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
HSDB
531
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
CAS
141-43-5
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
WIKIPEDIA
ETHANOLAMINE
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-483-3
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL104943
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
FDA UNII
5KV86114PT
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
DRUG BANK
DB03994
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY
MERCK INDEX
M5052
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
PRIMARY Merck Index
INN
497
Created by admin on Fri Jun 25 21:07:37 UTC 2021 , Edited by admin on Fri Jun 25 21:07:37 UTC 2021
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
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SALT/SOLVATE -> PARENT
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