Compounds > 4-methylmorpholine n-oxide
Page last updated: 2024-11-06

4-methylmorpholine n-oxide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-Methylmorpholine N-oxide (NMO) is a versatile oxidant widely used in organic synthesis. It is a colorless, crystalline solid that is soluble in water and most organic solvents. NMO is a mild and selective oxidant that is commonly employed for the oxidation of alcohols to aldehydes and ketones, the epoxidation of alkenes, and the oxidative cleavage of alkenes. NMO is typically synthesized by the oxidation of 4-methylmorpholine using hydrogen peroxide or peracetic acid. It is often used in combination with a catalytic amount of osmium tetroxide to achieve highly selective dihydroxylation of alkenes. NMO's selectivity, mild reaction conditions, and ease of handling make it a valuable reagent in organic synthesis. It is studied extensively for its synthetic applications, particularly in the development of new and efficient methods for the synthesis of pharmaceuticals and other fine chemicals.'

N-methylmorpholine N-oxide : A morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID82029
CHEMBL ID3184330
CHEBI ID52093
SCHEMBL ID1845
MeSH IDM0186106

Synonyms (103)

Synonym
n-methyl morpholine n-oxide
arc64pkj0f ,
ec 231-391-8
unii-arc64pkj0f
4-methylmorpholine 4-oxide, monohydrate
morpholine, 4-oxide
NCIOPEN2_000960
NCIOPEN2_000398
nsc-73198
7529-22-8
n-methylmorpholine oxide
nsc82153
nsc-82153
nsc73198
4-methylmorpholine 4-oxide
4-methyl-1,4.lambda.~5~-oxazinan-4-ol
morpholine, 4-methyl-, 4-oxide
4-methyl-4-oxido-morpholin-4-ium
NMO ,
4-methylmorpholine n-oxide, 97%
4-methylmorpholine-4-oxide
4-methylmorpholine n-oxide
einecs 231-391-8
nsc 73198
methyl morpholine oxide
nsc 82153
CHEBI:52093 ,
n-methylmorpholine n-oxide
n-methylmorpholine 4-oxide
C1367
4-methyl-4-oxidomorpholin-4-ium
n-methylmorpholine-n-oxide
inchi=1/c5h11no2/c1-6(7)2-4-8-5-3-6/h2-5h2,1h3
lftlokwagjyhhr-uhfffaoysa-
M0981
4-methyl-4-oxidanidyl-morpholin-4-ium
A840005
NCGC00248649-01
AKOS009159059
4-methyl morpholine n-oxide
dtxsid3029287 ,
NCGC00258033-01
cas-7529-22-8
tox21_200479
dtxcid509287
4-methylmorpholine oxide
nmmo
n-methylmorpholine n-oxide [mi]
methyl morpholine oxide [inci]
BP-30197
SCHEMBL1845
4-methyl morpholine-n-oxide
n-methylmopholine n-oxide
4-methylmorpholin-n-oxide
n-methylmorpholin-n-oxid
4-methylmorpholine-n- oxide
4-methyl-morpholine n-oxide
4methylmorpholine-n-oxide
n-methyl morpholin-n-oxide
methylmorpholine n-oxide
n-methymorpholine n-oxide
n-methyl-morpholine-n-oxide
4-methylmorpholine n oxide
4-methy-morpholine-n-oxide
4-methyl morpholine oxide
4-methylmorpholin-4-ium-4-olate
4-methyl morpholin n-oxide
n-methyimorpholine n-oxide
4-methylmorpholine-oxide
methylmorpholine-n-oxide
4-methyl-morpholine-4-oxide
4-methylmorpholine-n-oxide
4-methylmorpholine-n oxide
n-methyl-morpholine n-oxide
n-methylmorpholineoxide
n-methyl morpholine oxide
4-methyl-morpholine 4-oxide
n-methylmorphline n-oxide
4-methyl-morpholine-n-oxide
n-methyl morpholine-n-oxide
4-methyl morpholine-4-oxide
4methylmorpholine n-oxide
4-methylmopholine n-oxide
n-methyl morpholine-oxide
n-methyl-morpholine oxide
4-methyl-morpholine-n- oxide
4-methylnnorpholine n-oxide
4methylmorpholine-n oxide
4-methylmorpholin-4-oxide
4-methymorpholine n-oxide
n-methylmorpholin-n-oxide
W-104395
CHEMBL3184330
M2192
mfcd00005947
Q416248
Z381542114
EN300-37514
CS-0016218
D71257
4-methylmorpholine4-oxide
4-methylmorpholine n-oxide (50% in water, ca. 4.8mol/l)
PD055432
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
morpholine N-oxide
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency54.76630.000214.376460.0339AID720692
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (9.30)18.2507
2000's8 (18.60)29.6817
2010's30 (69.77)24.3611
2020's1 (2.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 52.93

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index52.93 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index81.21 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (52.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.22%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other44 (97.78%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1-butanol
1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.		2.3110alkyl alcohol;
primary alcohol;
short-chain primary fatty alcohol		human metabolite;
mouse metabolite;
protic solvent
methane
Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).		3.3660alkane;
gas molecular entity;
mononuclear parent hydride;
one-carbon compound		bacterial metabolite;
fossil fuel;
greenhouse gas
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		1.9710sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
glycerol
Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.		2.0610alditol;
triol		algal metabolite;
detergent;
Escherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
solvent
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.4920elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
sulfuric acid
sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.		2.1310sulfur oxoacidcatalyst
androsterone
[no description available]		2.071017-oxo steroid;
3alpha-hydroxy steroid;
androstanoid;
C19-steroid		androgen;
anticonvulsant;
human blood serum metabolite;
human metabolite;
human urinary metabolite;
mouse metabolite;
pheromone
dehydroepiandrosterone
Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.		1.981017-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
androstanoid		androgen;
human metabolite;
mouse metabolite
androstenedione
Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.		1.981017-oxo steroid;
3-oxo-Delta(4) steroid;
androstanoid		androgen;
Daphnia magna metabolite;
human metabolite;
mouse metabolite
17-alpha-hydroxyprogesterone
17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.		1.981017alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
tertiary alpha-hydroxy ketone		human metabolite;
metabolite;
mouse metabolite;
progestin
isobutyl alcohol
isobutyl alcohol: RN given refers to parent cpd		2.3110alkyl alcohol;
primary alcohol		Saccharomyces cerevisiae metabolite
4-methylmorpholine
[no description available]		2.0710
pregnenolone
[no description available]		1.981020-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
C21-steroid		human metabolite;
mouse metabolite
dihydrotestosterone
Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.		2.071017beta-hydroxy steroid;
17beta-hydroxyandrostan-3-one;
3-oxo-5alpha-steroid		androgen;
Daphnia magna metabolite;
human metabolite;
mouse metabolite
cellobiose
beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.		2.0710cellobioseepitope
dehydroepiandrosterone sulfate
Dehydroepiandrosterone Sulfate: The circulating form of a major C19 steroid produced primarily by the ADRENAL CORTEX. DHEA sulfate serves as a precursor for TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE.. dehydroepiandrosterone sulfate : A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.		1.981017-oxo steroid;
steroid sulfate		EC 2.7.1.33 (pantothenate kinase) inhibitor;
human metabolite;
mouse metabolite
sodium hydroxide
Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)		2.0310alkali metal hydroxide
rhenium
Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.		3.1910manganese group element atom
ruthenium
Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.		2.7130iron group element atom;
platinum group metal atom
stannic oxide
tin dioxide : A tin oxide compound consisting of tin(IV) covalently bound to two oxygen atoms.		2.0810tin oxide
osmium tetroxide
Osmium Tetroxide: (T-4)-Osmium oxide (OsO4). A highly toxic and volatile oxide of osmium used in industry as an oxidizing agent. It is also used as a histological fixative and stain and as a synovectomy agent in arthritic joints. Its vapor can cause eye, skin, and lung damage.. osmium tetroxide : An osmium coordination entity consisting of four oxygen atoms bound to a central osmium atom via covalent double bonds.		2.0510osmium coordination entityfixative;
histological dye;
oxidising agent;
poison
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.0510benzenes;
phenyl acetates
alkenes
[no description available]		3.5820
phenyliodosodiacetate
phenyliodosodiacetate: glycol-cleaving reagent used with amino alcohols in ring opening & Mannich base reactions; structure		2.0510
17-alpha-hydroxypregnenolone
17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.		1.981017alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
3beta-hydroxy-Delta(5)-steroid;
hydroxypregnenolone;
tertiary alpha-hydroxy ketone		human metabolite;
mouse metabolite
ruthenium tetraoxide
ruthenium tetraoxide: RN given refers to unlabeled cpd with MF of Ru-O4		3.1910
xylose
xylopyranose: structure in first source		2.0210D-xylose
perrhenate
perrhenate: RN given refers to cpd with MF of O4-Re		3.1910monovalent inorganic anion;
rhenium oxoanion
1-methyl-3-ethylimidazolium
1-methyl-3-ethylimidazolium: structure given in first source. 1-ethyl-3-methylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is ethyl.		2.07101-alkyl-3-methylimidazolium
lignin
Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.		3.250
cellulase
Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.		3.3360cellotriose
oleic acid
Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.		2.0810octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.1110chalcogen;
nonmetal atom		macronutrient
cellulose
DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.		4.27170glycoside
chitosan
[no description available]		2.0710
tetrapropylammonium perruthenate
tetrapropylammonium perruthenate: a catalytic oxidant used in conjunction with N-methylmorpholine N-oxide for oxidation of primary & secondary alcohols to aldehydes and ketones. tetrapropylammonium perruthenate : A quaternary ammonium salt having tetrapropylammonium as the cation and perruthenate as the anion.		3.5220
ConditionIndicatedRelationship StrengthStudiesTrials