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

Details

Stereochemistry ACHIRAL
Molecular Formula C2H7NO
Molecular Weight 61.0831
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOETHANOLAMINE

SMILES

NCCO

InChI

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

HIDE SMILES / InChI

Molecular Formula C2H7NO
Molecular Weight 61.0831
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
Developmental changes in choline- and ethanolamine-containing compounds measured with proton-decoupled (31)P MRS in in vivo human brain.
1999 Oct
Binding specificity of Bacillus thuringiensis Cry1Aa for purified, native Bombyx mori aminopeptidase N and cadherin-like receptors.
2001
Concentration verification of ethanol/nitrogen compressed gas cylinders prior to use for periodic determinations of accuracy in California.
2001 Apr
Chlorpromazine-induced increase in dipalmitoylphosphatidylserine surface area in monolayers at room temperature.
2001 Apr 1
Effects of homologues and analogues of palmitoylethanolamide upon the inactivation of the endocannabinoid anandamide.
2001 Aug
Ethanolamine transport in human placental brush-border membrane vesicles.
2001 Aug
Control of autofluorescence of archival formaldehyde-fixed, paraffin-embedded tissue in confocal laser scanning microscopy (CLSM).
2001 Dec
Protein kinase C activation by 12-0-tetradecanoylphorbol 13-acetate in CG-4 line oligodendrocytes stimulates turnover of choline and ethanolamine phospholipids by phospholipase D and induces rapid process contraction.
2001 Jan
Overexpression of a mammalian ethanolamine-specific kinase accelerates the CDP-ethanolamine pathway.
2001 Jan 19
Light-induced reorganization of phospholipids in rod disc membranes.
2001 Jan 26
Synthesis of a chiral aziridine derivative as a versatile intermediate for HIV protease inhibitors.
2001 Jul 26
[Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (Biovar I)].
2001 Jul-Aug
pH-sensitive paramagnetic liposomes as MRI contrast agents: in vitro feasibility studies.
2001 Jun
Optimized aminolysis conditions for cleavage of N-protected hydrophobic peptides from solid-phase resins.
2001 Jun
Structure and expression of the murine phosphatidylserine synthase-1 gene.
2001 Mar 16
Importance of barrier shape in enzyme-catalyzed reactions. Vibrationally assisted hydrogen tunneling in tryptophan tryptophylquinone-dependent amine dehydrogenases.
2001 Mar 2
The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase.
2001 Mar 9
Albibacter methylovorans gen. nov., sp. nov., a novel aerobic, facultatively autotrophic and methylotrophic bacterium that utilizes dichloromethane.
2001 May
Transport characteristics of peptides and peptidomimetics: II. Hydroxyethylamine bioisostere-containing peptidomimetics as substrates for the oligopeptide transporter and P-glycoprotein in the intestinal mucosa.
2001 May
Development of a tRNA-dependent in vitro translation system.
2001 May
Phospholipid composition of human sperm and seminal plasma in relation to sperm fertility.
2001 May-Jun
Nature of glycosylphosphatidylinositols produced by mouse embryonic stem cells.
2001 Nov
Luminol chemiluminescence in unbuffered solutions with a cobalt(II)-ethanolamine complex immobilized on resin as catalyst and its application to analysis.
2001 Nov 1
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
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
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
Detection of ligands for selectins in the oligosaccharide fraction of human milk.
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
New structures of the O-specific polysaccharides of bacteria of the genus Proteus. 1. Phosphate-containing polysaccharides.
2002 Feb
Regulation of phosphatidylcholine and phosphatidylethanolamine synthesis in rat hepatocytes by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR).
2002 Feb 15
Rapid synthesis and turnover of brain microsomal ether phospholipids in the adult rat.
2002 Jan
Endometriosis in reproductive immunology.
2002 May
Characterization of the hom-thrC-thrB cluster in aminoethoxyvinylglycine-producing Streptomyces sp. NRRL 5331.
2002 May
Expression and characterization of the active molecular forms of choline/ethanolamine kinase-alpha and -beta in mouse tissues, including carbon tetrachloride-induced liver.
2002 May 1
Stereochemical properties of lysophosphatidic acid receptor activation and metabolism.
2002 May 23
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 Sat Dec 16 17:35:35 GMT 2023
Edited
by admin
on Sat Dec 16 17:35:35 GMT 2023
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
IFOSFAMIDE IMPURITY D [EP IMPURITY]
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
Ethanolamine [WHO-DD]
Common Name English
2-Aminoethanol
Systematic Name English
ETHANOLAMINE [HSDB]
Common Name English
ETHANOLAMINE [MI]
Common Name English
OLAMINE
INN  
INN  
Official Name English
TROLAMINE IMPURITY A [EP IMPURITY]
Common Name English
ETHANOLAMINE [INCI]
Common Name English
Classification Tree Code System Code
LOINC 34300-4
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 28605-4
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LOINC 26608-0
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LOINC 56678-6
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LOINC 2264-0
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LOINC 13740-6
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NDF-RT N0000175814
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
NDF-RT N0000009905
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 15137-3
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LOINC 26593-4
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LOINC 15142-3
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 25910-1
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
EPA PESTICIDE CODE 11601
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
NDF-RT N0000020024
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 49633-1
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 32239-6
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LOINC 25098-5
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NCI_THESAURUS C29578
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
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 Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
FDA ORPHAN DRUG 416713
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 25405-2
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
LOINC 26803-7
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
Code System Code Type Description
CHEBI
23981
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022000
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
MESH
D019856
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
PUBCHEM
700
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
RXCUI
24457
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY RxNorm
CHEBI
16000
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
CHEBI
57603
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
NCI_THESAURUS
C61756
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
SMS_ID
100000092555
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
EVMPD
SUB01990MIG
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
HSDB
531
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
DAILYMED
5KV86114PT
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
CAS
141-43-5
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
WIKIPEDIA
ETHANOLAMINE
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-483-3
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL104943
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
FDA UNII
5KV86114PT
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
DRUG BANK
DB03994
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
MERCK INDEX
m5052
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1445925
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
INN
497
Created by admin on Sat Dec 16 17:35:38 GMT 2023 , Edited by admin on Sat Dec 16 17:35:38 GMT 2023
PRIMARY
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