MONOETHANOLAMINE

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 Search

SMILES

NCCO

InChI

InChIKey=HZAXFHJVJLSVMW-UHFFFAOYSA-N

InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28785375 | https://www.ncbi.nlm.nih.gov/pubmed/20938668 | Speight, G.J. (2015) Fouling in Refineries, page 358, retrieved from: https://books.google.ru/books?id=FeWcBAAAQBAJ

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Signal transducer and activator of transcription 3 10 Target ID: CHEMBL1764933 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20938668	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myocardial ischemia 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20938668	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Binding specificity of Bacillus thuringiensis Cry1Aa for purified, native Bombyx mori aminopeptidase N and cadherin-like receptors.	2001	11722800
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	11716783
Structure-activity relationship studies of (+/-)-terbutaline and (+/-)-fenoterol on beta3-adrenoceptors in the guinea pig gastric fundus.	2001 Aug	11885748
Liquid ionization mass spectrometry of some triorganotin carboxylates.	2001 Dec	11783790
Control of autofluorescence of archival formaldehyde-fixed, paraffin-embedded tissue in confocal laser scanning microscopy (CLSM).	2001 Dec	11724904
Beta 3 agonists. Part 1: evolution from inception to BMS-194449.	2001 Dec 3	11714605
Toxicity of amiodarone and amiodarone analogues on isolated rat liver mitochondria.	2001 Nov	11690709
Nature of glycosylphosphatidylinositols produced by mouse embryonic stem cells.	2001 Nov	11690539
Luminol chemiluminescence in unbuffered solutions with a cobalt(II)-ethanolamine complex immobilized on resin as catalyst and its application to analysis.	2001 Nov 1	11721898
Reductive demercuration in deprotection of trityl thioethers, trityl amines, and trityl ethers.	2001 Nov 16	11701012
Confocal and probe microscopy to study gene transfection mediated by cationic liposomes with a cationic cholesterol derivative.	2001 Nov 19	11718944
Tissue-specific and developmental effects of the easily shocked mutation on ethanolamine kinase activity and phospholipid composition in Drosophila melanogaster.	2001 Oct	11758729
Maternal-fetal n-6 and n-3 polyunsaturated fatty acids gradient in plasma and red cell phospholipids.	2001 Sep	11725693
Poly(amide ester)s from 2,6-pyridinedicarboxylic acid and ethanolamine derivatives: identification of macrocycles by matrix-assisted laser desorption/ionization mass spectrometry.	2002	12125025
[Structural and metabolic status and functional properties of erythrocytes in schizophrenic patients].	2002	12101891
Ethanolamine is a co-mitogenic factor for proliferation of primary hepatocytes.	2002	11787054
Thermal study of simple amino-alcohol solutions.	2002 Apr	12151270
Detection of ligands for selectins in the oligosaccharide fraction of human milk.	2002 Apr	12083318
Glycosylphosphatidylinositol (GPI)-anchored proteins.	2002 Apr	11995915
Mutations inducing divergent shifts of constitutive activity reveal different modes of binding among catecholamine analogues to the beta(2)-adrenergic receptor.	2002 Apr	11934812
Endoscopic management and long-term follow-up of Dieulafoy's lesions in the upper GI tract.	2002 Apr	11923766
Amiodarone-induced phospholipidosis: an in vivo [14C]-acetate uptake study in rat.	2002 Aug	12173246
Phosphatidyl ethanolamine is essential for targeting the arginine transporter Can1p to the plasma membrane of yeast.	2002 Aug 19	12100990
Evaluation and optimization of DNA delivery into gliosarcoma 9L cells by a cholesterol-based cationic liposome.	2002 Aug 31	12175922
New structures of the O-specific polysaccharides of bacteria of the genus Proteus. 1. Phosphate-containing polysaccharides.	2002 Feb	11952425
(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	11897338
Cytoskeletal inhibitors, anti-adhesion molecule antibodies, and lectins inhibit hepatocyte spheroid formation.	2002 Feb	11873944
Regulation of phosphatidylcholine and phosphatidylethanolamine synthesis in rat hepatocytes by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR).	2002 Feb 15	11829744
Kinetic analyses of liver phosphatidylcholine and phosphatidylethanolamine biosynthesis using (13)C NMR spectroscopy.	2002 Feb 28	11880242
Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance.	2002 Feb-Mar	12052034
Rapid synthesis and turnover of brain microsomal ether phospholipids in the adult rat.	2002 Jan	11792723
Dietary n-3 and n-6 fatty acids alter avian metabolism: molecular-species composition of breast-muscle phospholipids.	2002 Jul	12117424
Algicidal effectiveness of Clearigate, Cutrine-Plus, and copper sulfate and margins of safety associated with their use.	2002 Jul	12045870
Computational exploration of rearrangements related to the vitamin B12-dependent ethanolamine ammonia lyase catalyzed transformation.	2002 Jul 31	12137553
Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor.	2002 Jun	12023533
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	12039631
Comparative study of the effects of short- and long-term ethanol treatment and alcohol withdrawal on phospholipid biosynthesis in rat hepatocytes.	2002 Mar	11959031
Saccharomonospora halophila sp. nov., a novel halophilic actinomycete isolated from marsh soil in Kuwait.	2002 Mar	11931168
Coamplification of DAD-R, SOX5, and EKI1 in human testicular seminomas, with specific overexpression of DAD-R, correlates with reduced levels of apoptosis and earlier clinical manifestation.	2002 Mar 15	11912161
Extracellular release of the glycosylphosphatidylinositol (GPI)-linked Leishmania surface metalloprotease, gp63, is independent of GPI phospholipolysis: implications for parasite virulence.	2002 Mar 15	11777912
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	11906284
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	11999740
Endometriosis in reproductive immunology.	2002 May	12148541
Phospholipid biosynthesis in the oyster protozoan parasite, Perkinsus marinus.	2002 May	12034458
Characterization of the hom-thrC-thrB cluster in aminoethoxyvinylglycine-producing Streptomyces sp. NRRL 5331.	2002 May	11988515
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	11964179
Stereochemical properties of lysophosphatidic acid receptor activation and metabolism.	2002 May 23	12069841
Structure-activity relationships of lysophosphatidic acid analogs.	2002 May 23	12069840
Phosphomonoester concentrations differ between chronic lymphocytic leukemia cells and normal human lymphocytes.	2002 Oct	12163053
Involvement of delta-aminolaevulinate synthase encoded by the parasite gene in de novo haem synthesis by Plasmodium falciparum.	2002 Oct 15	12119044

Patents

Sample Use Guides

In Vivo Use Guide

Rat: single injection 5 mg/kg of S1P

Route of Administration: Intravenous

In Vitro Use Guide

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.

Name

Type

Language

MONOETHANOLAMINE

Systematic Name

English

MONOETHANOLAMINE [II]

Common Name

English

IFOSFAMIDE IMPURITY D [EP IMPURITY]

Common Name

English

ETHANOLAMINE

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

Official Name

English

TROLAMINE IMPURITY A [EP IMPURITY]

Common Name

English

ETHANOLAMINE [INCI]

Common Name

English

Classification Tree Code System Code

LOINC

34300-4