Ethanolamines
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Ethanolamines
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia. Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEOA). The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine. History Ethanolamines, or in particular, their salts, were discovered by Charles Adolphe Wurtz in 1860 by heating 2-Chloroethanol, 2-chloroethanol with ammonia solution while studying derivatives of ethylene oxide he discovered a year earlier. He wasn't able to separate the salts or isolate any free bases. In 1897 Ludwig Knorr deve ...
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N-Methylethanolamine
''N''-Methylethanolamine is an alkanolamine with the formula CH3NHCH2CH2OH. It is flammable, corrosive, colorless, viscous liquid.Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke "Ethanolamines and Propanolamines" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2002, Wiley-VCH, Weinheim. It is an intermediate in the biosynthesis of choline. With both an amine and a hydroxyl functional groups, it is a useful intermediate in the chemical synthesis of various products including polymers and pharmaceuticals. It is also used as a solvent, for example in the processing of natural gas, where it is used together with its analogs ethanolamine and dimethylethanolamine. Production ''N''-Methylethanolamine is produced industrially by reacting ethylene oxide with excess methylamine in aqueous solution. This reaction yields a mixture of the 1:1 addition product NMEA (1) and - by a further addition of another ethylene oxide - the 1:2 addi ...
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Ethanolamine
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia. Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEOA). The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine. History Ethanolamines, or in particular, their salts, were discovered by Charles Adolphe Wurtz in 1860 by heating 2-chloroethanol with ammonia solution while studying derivatives of ethylene oxide he discovered a year earlier. He wasn't able to separate the salts or isolate any free bases. In 1897 Ludwig Knorr deve ...
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Amino Alcohols
In organic chemistry, alkanolamines (amino alcohols) are organic compounds that contain both hydroxyl () and amino (, , and ) functional groups on an alkane backbone. Alkanolamine's bifunctionality and physicochemical characteristics lead to its use in many applications, such as Textile, textiles, cosmetics, agricultural chemical intermediates, drugs, and Cutting fluid, metal working fluids. Many aminoalcohols derivatives also have Chemotherapy, chemotherapeutic properties. Methanolamine.svg, Methanolamine, from the reaction of ammonia with formaldehyde Ethanolamine.svg, Ethanolamine 2-amino-2-methyl-1-propanol.svg, 2-Amino-2-methyl-1-propanol is a precursor to oxazolines valinol.svg, Valinol is derived from the amino acid valine Sphingosine structure.svg, Sphingosine is a component of some cell membrane, cell membranes. Alkanolamines usually have high-solubility in water due to the hydrogen Hydrogen bond, bonding ability of both the hydroxyl group and the amino group. Alkano ...
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Doxylamine
Doxylamine is an antihistamine medication used to treat insomnia and allergies, and—in combination with pyridoxine ( vitamin B6)—to treat morning sickness in pregnant women. It is available over-the-counter and is sold under such brand names as Equate or Unisom, among others; and it is used in nighttime cold medicines (e.g., NyQuil) and pain medications containing paracetamol (acetaminophen) or codeine to help with sleep. The medication is delivered chemically by the salt doxylamine succinate and is taken by mouth. Doxylamine and other first-generation antihistamines are the most widely used sleep medications in the world. Typical side effects of doxylamine include dizziness, drowsiness, grogginess, and dry mouth, among others. As an antihistamine, doxylamine is an inverse agonist of the histamine H1 receptor. As a first-generation antihistamine, it typically crosses the blood–brain barrier into the brain, thereby producing a suite of sedative and hypnotic effects ...
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Diethanolamine
Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool often results in it being found in a colorless, viscous liquid state. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" ( Group 2B). Production The reaction of ethylene oxide with aqueous ammonia first produces ethanolamine: :C2H4O + NH3 → H2NCH2CH2OH which reacts with a second and third equivalent of ethylene oxide to give DEA and triethanolamine: :C2H4O + H2NCH2CH2OH → HN(CH2CH2OH)2 :C2H4O + ...
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Triethanolamine
Triethanolamine, or TEOA, is an organic compound with the chemical formula . It is a colourless, viscous liquid. It is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples may appear yellow because of impurities. Production Triethanolamine is produced from the reaction of ethylene oxide with aqueous ammonia, also produced are ethanolamine and diethanolamine. The ratio of the products can be controlled by changing the stoichiometry of the reactants. : Applications Triethanolamine is used primarily in making surfactants, such as for emulsifier. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizes fatty acids, adjusts and buffers the pH, and solubilizes oils and other ingredients that are not completely soluble in water. Triethanolammonium salts in some cases are more soluble ...
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Ethylene Oxide
Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst. The reactivity that is responsible for many of ethylene oxide's hazards also makes it useful. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used for making many consumer products as well as non-consumer chemicals and intermediates. These products include detergents, thickeners, solvents, plastics, and various organic chemicals such as ethylen ...
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Diethanolamine
Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool often results in it being found in a colorless, viscous liquid state. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" ( Group 2B). Production The reaction of ethylene oxide with aqueous ammonia first produces ethanolamine: :C2H4O + NH3 → H2NCH2CH2OH which reacts with a second and third equivalent of ethylene oxide to give DEA and triethanolamine: :C2H4O + H2NCH2CH2OH → HN(CH2CH2OH)2 :C2H4O + ...
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Chlorphenoxamine
Chlorphenoxamine (Phenoxene) is an antihistamine and anticholinergic used as an antipruritic and antiparkinsonian agent. It is an analog of diphenhydramine Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. Although generally considered sedating, diphenhydramine can cause paradoxical central nervous system stimulation in some individuals, particula .... References H1 receptor antagonists 4-Chlorophenyl compounds Ethers Dimethylamino compounds {{nervous-system-drug-stub ...
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Diphenhydramine
Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. Although generally considered sedating, diphenhydramine can cause paradoxical central nervous system stimulation in some individuals, particularly at higher doses. This may manifest as agitation, anxiety, or restlessness rather than sedation. It is a H1 antagonist#First-generation (non-selective, classical), first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects. Diphenhydramine is also a potent anticholinergic. It is mainly used to treat allergy, allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremors in parkinsonism, and nausea. It is taken oral administration, by mouth, injection into a vein, injected into a vein, injection into a muscle, injected into a muscle, or topical medication, applied to the skin. Maximal effect is typically around two hours af ...
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Ammonia Solution
Ammonia solution, also known as ammonia water, ammonium hydroxide, ammoniacal liquor, ammonia liquor, aqua ammonia, aqueous ammonia, or (inaccurately) ammonia, is a solution of ammonia in water. It can be denoted by the symbols NH3(aq). Although the name ammonium hydroxide suggests a salt with the composition , it is impossible to isolate samples of NH4OH. The ions and OH− do not account for a significant fraction of the total amount of ammonia except in extremely dilute solutions. The concentration of such solutions is measured in units of the Baumé scale (density), with 26 degrees Baumé (about 30% of ammonia by weight at ) being the typical high-concentration commercial product. Basicity of ammonia in water In aqueous solution, ammonia deprotonates a small fraction of the water to give ammonium and hydroxide according to the following equilibrium: : NH3 + H2O ⇌ + OH−. In a 1  M ammonia solution, about 0.42% of the ammonia is converted to ammonium, equivalent ...
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