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
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
Characterization of the lipopolysaccharide and structure of the O-specific polysaccharide of the bacterium Pseudomonas syringae pv. atrofaciens IMV 948.
2001 Apr
Structure-activity relationship studies of (+/-)-terbutaline and (+/-)-fenoterol on beta3-adrenoceptors in the guinea pig gastric fundus.
2001 Aug
Ethanolamine transport in human placental brush-border membrane vesicles.
2001 Aug
Beta 3 agonists. Part 1: evolution from inception to BMS-194449.
2001 Dec 3
Construction of phosphatidylethanolamine-less strain of Saccharomyces cerevisiae. Effect on amino acid transport.
2001 Feb
Chronic ingestion of ethanol stimulates lipogenic response in rat hepatocytes.
2001 Feb 2
Optimized aminolysis conditions for cleavage of N-protected hydrophobic peptides from solid-phase resins.
2001 Jun
Kinetics of removal of carbonyl sulfide by aqueous monoethanolamine.
2001 Jun 1
Suicide through doxylamine poisoning.
2001 Jun 1
Preparation of potent cytotoxic ribonucleases by cationization: enhanced cellular uptake and decreased interaction with ribonuclease inhibitor by chemical modification of carboxyl groups.
2001 Jun 26
Modified phosphatidylethanolamine as the active component of oxidized low density lipoprotein promoting platelet prothrombinase activity.
2001 Jun 8
Resveratrol inhibits the formation of phosphatidic acid and diglyceride in chemotactic peptide- or phorbol ester-stimulated human neutrophils.
2001 Mar
The immunodominant 17-kDa antigen from Cryptosporidium parvum is glycosylphosphatidylinositol-anchored.
2001 Mar
Development of an electrochemical immunosensor for direct detection of interferon-gamma at the attomolar level.
2001 Mar 1
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
Toxicity of amiodarone and amiodarone analogues on isolated rat liver mitochondria.
2001 Nov
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
Reductive demercuration in deprotection of trityl thioethers, trityl amines, and trityl ethers.
2001 Nov 16
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
Phosphatidylethanolamine participates in the stimulation of the contact system of coagulation by very-low-density lipoproteins.
2001 Oct
Polar nitrogen compounds and their behaviour in the drinking water treatment process.
2001 Oct
Early ethanolamine phospholipid translocation marks stress-induced apoptotic cell death in oligodendroglial cells.
2001 Sep
Plants synthesize ethanolamine by direct decarboxylation of serine using a pyridoxal phosphate enzyme.
2001 Sep 21
[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
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
(Aminoethanol)dichloroplatinum(II) complexes: influence of the hydroxyethyl moiety on 5'-GMP and DNA binding, intramolecular stability, the partition coefficient and anticancer activity.
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
Dietary n-3 and n-6 fatty acids alter avian metabolism: molecular-species composition of breast-muscle phospholipids.
2002 Jul
Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor.
2002 Jun
Saccharomonospora halophila sp. nov., a novel halophilic actinomycete isolated from marsh soil in Kuwait.
2002 Mar
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
Structure-activity relationships of lysophosphatidic acid analogs.
2002 May 23
Phosphomonoester concentrations differ between chronic lymphocytic leukemia cells and normal human lymphocytes.
2002 Oct
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 UTC 2023
Edited
by admin
on Sat Dec 16 17:35:35 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 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
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
NDF-RT N0000175814
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
NDF-RT N0000009905
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 15137-3
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 26593-4
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 15142-3
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 25910-1
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
EPA PESTICIDE CODE 11601
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
NDF-RT N0000020024
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 49633-1
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 13613-5
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LOINC 6881-7
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LOINC 2263-2
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 25911-9
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
FDA ORPHAN DRUG 416713
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 25405-2
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
LOINC 26803-7
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
Code System Code Type Description
CHEBI
23981
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID6022000
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
MESH
D019856
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
PUBCHEM
700
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
RXCUI
24457
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY RxNorm
CHEBI
16000
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
CHEBI
57603
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
NCI_THESAURUS
C61756
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
SMS_ID
100000092555
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
EVMPD
SUB01990MIG
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
HSDB
531
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
DAILYMED
5KV86114PT
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
CAS
141-43-5
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
WIKIPEDIA
ETHANOLAMINE
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-483-3
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL104943
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
FDA UNII
5KV86114PT
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
DRUG BANK
DB03994
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
MERCK INDEX
m5052
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1445925
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
INN
497
Created by admin on Sat Dec 16 17:35:38 UTC 2023 , Edited by admin on Sat Dec 16 17:35:38 UTC 2023
PRIMARY
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