An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R₃N⁺-O⁻ (sometimes written as R₃N=O or R₃N→O). In the strict sense the term amine oxide applies only to oxides of tertiary amines including nitrogen-containing aromatic compounds like pyridine, but is sometimes also used for the analogous derivatives of primary and secondary amines. A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Ammonia Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... Simple aromatic rings are aromatic organic compounds (also known as arenes or aromatics) that consist only of conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds. ... R-phrases , , , S-phrases , , Flash point 20 °C Supplementary data page Structure and properties n, εr, etc. ...

Amine oxides are used as protecting group for amines and as chemical intermediates. Long-chain alkyl amine oxides are used as nonionic surfactants and foam stabilizers. A Protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction. ... In chemistry, the phrase chemical synthesis appears to have one of two meanings. ... An Alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... An ion is an atom or group of atoms with a net electric charge. ... Surfactants are wetting agents that lower the surface tension of a liquid, allowing easier spreading, and lower the interfacial tension between two liquids. ... Foam The most general definition of foam is a substance that is formed by trapping many gas bubbles in a liquid or solid. ...

Amine oxide are highly polar molecules have a high polarity close to that of quaternary ammonium salts. Small amine oxides are very hydrophilic and have an excellent water solubility and a very poor solubility in most organic solvents. A commonly-used example of a polar compound is water (H2O). ... layers]] that separate organs or subcompartments in organisms. ... Quaternary ammonium cation. ... The adjective hydrophilic describes something that likes water (from Greek hydros = water; philos = friend). ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... A substance is soluble in a fluid if it dissolves in that fluid. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ...

Amine oxides are weak bases with a pK_a of around 4.5 that form R₂N⁺-OH, cationic hydroxylamines, upon protonation at a pH below their pK_a. It has been suggested that strong base be merged into this article or section. ... In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... A cation is an ion with positive charge. ... The compound hydroxylamine is a nitrogen-containing base whose chemical formula is NH2OH, and is therefore a close relative of the compound ammonia. ... Protonation is the addition of a proton (H+) to an atom, molecule, or ion. ... PH or ph or pH or Ph may be: pH, a measure of acidity (chemistry) Ph, a phenyl ring (organic chemistry) PH, the ISO country code of the Philippines (see . ...

Synthesis

Amine oxides are prepared by oxidation of tertiary amines or pyridine analogs with hydrogen peroxide (H₂O₂) or peracids like mCPBA. The most fundamental reactions in chemistry are the redox processes. ... Hydrogen peroxide (H2O2) is a clear liquid, slightly more viscous than water, that has strong oxidizing properties and is therefore a powerful bleaching agent that has found use as a disinfectant, as an oxidizer, and in rocketry (particularly in high concentrations as high-test peroxide (HTP) as a monopropellant), and... Chemical structure of meta-chloroperoxybenzoic acid meta-Chloroperoxybenzoic acid (mCPBA) is a peroxy acid with chemical formula C7H5ClO3 and CAS number 937-14-4. ...

Reactions

Pyrolytic elimination

Amine oxides, when heated to 150 to 200 ºC eliminate a hydroxylamine, resulting in an alkene. This pyrolytic syn-elimination reaction is known under the name Cope reaction. The mechanism is similar to that of the Hofmann elimination. An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... Pyrolysis is formally defined as chemical decomposition of organic materials by heating in the absence of oxygen or any other reagents. ... An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism. ... It has been suggested that this article or section be merged into Cope rearrangement. ... Hofmann elimination provides the dealkylation of quaternary ammonium salts to tertiary amines due to the scheme: quaternary ammonium salt via 1. ...

Reduction to amines

Amine oxides are readily converted to the parent amine by common reduction reagents including lithium aluminum hydride, sodium borohydride, catalytic reduction, zinc / acetic acid, and iron / acetic acid. Reduction or reducing has several meanings: In mathematics, reduction is the process of manipulating a series of equations or matrices into a desired simpler format. ... When purchasing or preparing chemicals, reagent describes chemical substances of sufficient purity for use in chemical analysis, chemical reactions or physical testing. ... Lithium aluminum hydride (LiAlH4, commonly abbreviated to LAH) is a powerful reducing agent used in organic chemistry. ... Sodium borohydride, also known as sodium tetrahydridoborate, has the chemical formula NaBH4 (CAS 16940-66-2). ... General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Atomic mass 65. ... Flash point 43 Â°C R-phrases , S-phrases , , , U.S. Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... General Name, Symbol, Number iron, Fe, 26 Chemical series transition metals Group, Period, Block 8, 4, d Appearance lustrous metallic with a grayish tinge Atomic mass 55. ...

Metabolites

Amine oxides are common metabolites of medication and psychoactive drugs. Examples include nicotine, Zolmitriptan, and morphine. Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms and cells. ... Oral medication A medication is a licenced drug taken to cure or reduce symptoms of an illness or medical condition. ... A psychoactive drug or psychotropic substance is a chemical that alters brain function, resulting in temporary changes in perception, mood, consciousness, or behavior. ... Nicotine is an organic compound, a pyrrolidine-like alkaloid found naturally in the nightshade family of plants, such as tobacco and tomatoes. ... Zolmitriptan is an oral, selective 5-hydroxytryptamine 1B/1D (5-HT 1B/1D ) receptor agonist, or triptan, for acute treatment of migraine attacks with or without aura. ... See Morphia for the Dutch metal band. ...

Prodrugs

Amine oxides of anti-cancer drugs have been developed as prodrugs that are metabolized in the oxygen deficient cancer tissue to the active drug. Chemotherapy is the use of chemical substances to treat disease. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... When normal cells are damaged beyond repair, they are eliminated by apoptosis. ... Biological tissue is any substance made up of cells that perform a similar function within an organism. ...

See also

• Functional group
• Amine, NR₃
• Hydroxylamine, NR₂OH
• Sulfoxide, R₂S=O
• Azoxy, RN=N+(O–)R RN=N⁺RO⁻
• N-Methylmorpholine N-oxide, an amine oxide
• TEMPO (2,2,6,6-Tetramethylpiperidine-1-oxyl), a stable amine oxide radical

In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Ammonia Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... The compound hydroxylamine is a nitrogen-containing base whose chemical formula is NH2OH, and is therefore a close relative of the compound ammonia. ... A sulfoxide is a chemical compound containing a sulfinyl functional group with a sulfur oxygen double bond attached to two carbon atoms. ... N-methylmorpholine-N-Oxide or NMO is an organic compound. ... In musical terminology, tempo (Italian for time) is the speed or pace of a given piece. ...

External links

• Chemistry of amine oxides
• Surfactants, types and uses (pdf)
• The amine oxides homepage
• Nomenclature of nitrogen compounds
• IUPAC definition (pdf)