Dimethylethanolamine
EC / List no.: 203-542-8
CAS no.: 108-01-0
Mol. formula: C4H11NO
Molar mass: 89.14 g·mol−1
Dimethylaminoethanol = Dimethylethanolamine = DMAE = DMEEA = N,N-DIMETHYLAMINOETHANOL = 2-DIMETHYLAMINOETHANOL = DMEOA
Chemical synonyms: N,N-Dimethylethanolamine; Dimethylethanolamine; Deanol; DMEA; N,N-Dimethyl-2-Hydroxyethylamine; N,N-Dimethyl-N-ethanolamine
2-DIMETHYLAMINO-ETHANOL
2-dimethylaminoethanol
2-DIMETHYLAMINOETHANOL
2-dimethylaminoethanol
2-dimethylaminoethanol
N,N-dimethylethanolamine
Deanol
dimethylaminoethanol
DMEA
DMAE
2-(Dimethylamino)ethanol
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Main Applications: flocculating agent, ion-exchange resin, urethane catalyst
Dimethylethanolamine is a clear to pale-yellow liquid used as a curing agent for polyurethanes and epoxy resins, in water treatment, and in the synthesis of various products.
Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care products for improving skin tone and also taken orally as a nootropic. It is prepared by the ethoxylation of dimethylamine.
Dimethylaminoethanol, also known as dimethylethanolamine (DMAE and DMEA respectively), is a primary alcohol.
This compound also goes by the names of N,N-dimethyl-2-aminoethanol, beta-dimethylaminoethyl alcohol, beta-hydroxyethyldimethylamine and Deanol.
Dimethylethanolamine is a transparent, pale-yellow liquid.
Dimethylethanolamine is used as a curing agent for polyurethanes and epoxy resins; used as a chemical intermediate for pharmaceuticals, dyes, corrosion inhibitors, and emulsifiers; also used as an additive to boiler water, paint removers, and amino resins; [HSDB] Has been used therapeutically as a CNS stimulant; [Merck Index # 2843]
Dimethylethanolamine, also known as Dimethylaminoethanol (DMEA and DMAE respectively), is an organic compound which is industrially produced by the reaction of ethylene oxide with dimethylamine.
Dimethylethanolamine contains both an amine group and a hydroxyl group, and can therefore react as as an amine or an alcohol. It is a transparent, pale-yellow liquid
Dimethylethanolamine is used as a catalyst, corrosion inhibitor, additive to paint removers/boiler, water/amino resins and it is used in cosmetic and biomedical products.
N,N-dimethylethanolamine is a tertiary amine that is ethanolamine having two N-methyl substituents.
N,N-dimethylethanolamine has a role as a curing agent and a radical scavenger.
N,N-dimethylethanolamine is a tertiary amine and a member of ethanolamines.
Dimethylethanolamine (DMEA) is an amino alcohol, organic compound. It is obtained in industry by synthesis of ethylene oxide and dimethylamine.
Dimethylethanolamine is a transparent, slightly yellow liquid. It is miscible with water, acetone, ether, and benzene.
Dimethylethanolamine is used as a curing agent for epoxy resins and polyurethanes.
It is also used in the intermediate synthesis of dyestuffs, textiles, pharmaceuticals, and corrosion inhibitors. Another application is an emulsifier in paints and coatings.
The main areas for dimethylethanolamine application are: the production of initial monomers for water treatment, as a catalyst for polyurethane foam and ion exchange resins. In addition, DMEA is used in the chemical, paint and varnish, pharmaceutical and textile industries.
USES of Dimethylethanolamine:
Dimethylethanolamine (DMEA) is commonly used substance in the formulation of cosmetics related to skin care application.
Its chemical formula is (CH3)2NCH2CH2OH.
Dimethylethanolamine is prepared by the ethoxylation of dimethylamine.
Rising population and urbanization has boosted the demand for cosmetics products, thus driving the Dimethylethanolamine (DMEA) market.
Dimethylethanolamine is a precursor to other chemicals, such as the nitrogen mustard 2-dimethylaminoethyl chloride.
It ranges from colorless to slightly yellow liquid with an amine-like odor.
Dimethylethanolamine (DMEA) is extensively utilized in the water treatment industry.
Dimethylethanolamine is also used as a polyurethane catalyst in coatings applications and as an intermediate in textile chemicals, ion exchange resins, and emulsifying agents.
DMEA is also employed in the pharmaceutical industry as a supplement form to boost brain health by raising acetylcholine levels.
INDUSTRIAL USES of Dimethylethanolamine :
Dimethylethanolamine is used as a curing agent for polyurethanes and epoxy resins.
Dimethylethanolamine is also used in mass quantities for water treatment, and to some extent in the coatings industry.
Dimethylethanolamine is used in the synthesis of dyestuffs, textile auxiliaries, pharmaceuticals, emulsifiers, and corrosion inhibitors.
Dimethylethanolamine is also an additive to paint removers, boiler water and amino resins.
Dimethylethanolamine forms a number of salts with melting points below room temperature (ionic liquids) such as N,N-dimethylethanolammonium acetate and N,N-dimethylethanolammonium octanoate, which have been used as alternatives to conventional solvents.
Dimethylethanolamine in Water Treatment Industry:
Dimethylethanolamine is a neutralizing amine.
Dimethylethanolamine (DMEA) effectively neutralizes the condensate without resulting in appreciable deposit formation.
Organic amines are corrosion control agents that increase pH and scavenge corrosive contaminants.
Dimethylethanolamine (DMEA), for example, is a common corrosion inhibitor that eliminates dissolved CO2 and helps control pH in industrial boilers and nuclear power plants.
Amines are also effective as hydrogen sulfide scavengers in oil and gas production and processing.
On-site monitoring for amines can help maintain appropriate corrosion protection, extending system lifetime and avoiding costly corrosion-induced shutdowns and failures.
N,N-dimethylethanolamine has role curing agent
N,N-dimethylethanolamine has role radical scavenger
N,N-dimethylethanolamine is a ethanolamines
N,N-dimethylethanolamine is a tertiary amine
2-Dimethylaminoethyl chloride hydrochloride is an intermediate made from Dimethylethanolamine that is widely used for the manufacture of pharmaceuticals.
Flocculants: DMEA is a key intermediate in the production of dimethylaminoethyl-(meth)acrylate. The water-soluble polymers produced from this ester, mostly by copolymerisation with acrylamide, are useful as flocculents.
Pulp and paper chemicals: The dry strength or wet strength of paper is increased by adding a homopolymer of dimethylaminoethyl(meth)acrylate to the unbleached kraft paper.
Ion exchange resins: Anion exchange resins can be prepared by reacting tertiary amines like DMEA or trimethylamine with the chloromethylated vinyl or styrene resin.
Increased exchange capacity is obtained by reacting a cross-linked polymer, containing haloalkyl functions, with an amine.
The anion exchange membranes are aminated with DMEA.
Polyurethane: In the production of PU foam for insulating purposes, the use of DMEA is a practical and effective way of reducing the total formula cost.
Resins
Epoxy
DMEA is an effective and versatile curing agent for epoxy resins. It also acts as viscosity reducing agent for resinous polyamides and other viscous hardeners.
DMEA is also an extremely good wetting agent for various filters in epoxy formulations.
DMEA, also known as dimethylethanolamine (DMEA), is a curing agent for epoxy resins.
2-Dimethylethanolamine is miscible with water, alcohols, ether, and aromatic solvents. It undergoes reactions typical of amines and alcohols. It is used in the preparation of waterborne (WB) coatings formulations.
Acrylic
DMEA improves the acid-dyeing properties of acrylonitrile polymers by copolymerisation of DMEA esters.
Water-soluble DMEA salts are used to improve the behaviour of coatings and films to make them water-resistant or provide specific desired sensitivity to water.
Textiles – leather: The acid-dyeing capability of polyacrylonitrile is improved by copolymerisation of the acrylonitrile with DMEA esters, such as dimethylaminoethyl acrylate.
Cellulose modified with the homopolymer of dimethylaminoethyl methacrylate can be dyed with ester salts of a leuco vat dye.
The impregnation of cellulose with polydimethylaminoethyl methacrylate also improves the gas-fading resistance of the fabric.
Long-chain alkylphosphates of DMEA form anti-static agents for non-cellulosic hydrophobic textile materials.
Paints, coatings and inks: DMEA is excellent for neutralising free acidity in water-soluble coating resins. The resin can be acrylic, alkyd or styrene-maleic. DMEA is often preferred to triethylamine when lower volatility is required, as in electrodeposition. It also improves pigment wettability.
Some synthetic enamels with a metallic appearance can be prepared from dimethylaminoethyl methacrylate polymers.
In flexographic inks DMEA can be used to solubilize resins and inoxes.
The adhesion of latex coatings can be improved by copolymerisation of the acrylic monomers with dimethylaminoethyl acrylate.
Surfactants – detergents: Alkylethanolamine salts of anionic surfactants are generally much more soluble than the corresponding sodium salts, both in water and oil systems. DMEA can be an excellent starting material in the production of shampoos from fatty acids. The fatty acid soaps are especially effective as wax emulsifiers for water-resistant floor polishes.
DMEA titanates, zirconates and other group IV-A metal esters are useful as dispersing agents for polymers, hydrocarbons and waxes in aqueous or organic solvent systems.
Applications/uses
Paints & coatings
Dimethylethanolamine (DMEA): Application Segment
In terms of application, the global Dimethylethanolamine (DMEA) market can be segmented into cleansing agent, antibacterial agent, flocculating agent, urethane catalyst, ion-exchange resin, emulsifying agent, and others
The cleansing agent segment is expected to account for a significant share of the global Dimethylethanolamine (DMEA) market.
It is anticipated to be followed by the flocculating agent segment.
The ion-exchange resin segment is likely to expand at a rapid pace, due to the expansion of polymer industry around the globe
Dimethylethanolamine (DMEA): End-use Segment
In terms of end-use, the global Dimethylethanolamine (DMEA) market can be segmented into pharmaceutical, chemical, cosmetics, and others
The cosmetics segment is estimated to expand at a rapid pace.
It is projected to be followed by the pharmaceutical industry segment.
Dimethylethanolamine (DMEA)
DMEA is a novel ingredient initially used in the treatment of hyperkinetic disorders and to improve memory.
It is now being used in cosmeceutical products, gaining popularity from its activity as a precursor to acetylcholine.
Initially utilized as a firming and anti-aging product, new functions, including anti-inflammatory and antioxidant activities, have now been elucidated.
In vitro, DMEA inhibits IL-2 and IL-6 secretion in addition to its actions as a free radical scavenger.
Although the exact mechanism of action of DMEA is unclear, its acetylcholine-like functions increase contractility and cell adhesion in the epidermis and dermis, resulting in the appearance of firmer skin.
PHARMA USE OF Dimethylethanolamine:
DMEA is also known as Dimethylethanolamine, 2-Dimethylaminoethanol or Deanol, is an analog of the vitamin B choline (N,N,N-trimethylethanolamine) and is a precursor of acetylcholine 1).
DMEA was thought to be a precursor for acetylcholine, has been tested for its efficacy in treating a variety of diseases possibly related to deficiencies of acetylcholine, including tardive dyskinesia, Alzheimer’s disease, amnesic disorders, age-related cognitive impairment, attention deficit-hyperactivity disorder (ADHD), Tourette’s syndrome, autism and tardive dyskinesia with mixed results.
Three reported no benefit from DMEA treatment (tardive dyskinesia; cognitive dysfunction; Alzheimer’s disease).
Treatment with DMEA for tardive dyskinesia, a side effect of neuroleptic medications, was associated with serious cholinergic side effects: nasal and oral secretions, dyspnea, and respiratory failure 3).
DMEA was used in the treatment of one patient for a low-frequency action tremor.
This treatment was successful for ten years, until side effects of increasing neck pain and orofacial and respiratory dyskinesia occurred.
Treatment was discontinued, and it was concluded that the dyskinesia could be attributed to the effects of DMEA.
A meta-analysis of randomized controlled trials indicated that DMEA was no more effective than placebo in the treatment of tardive dyskinesia.
Rather, there was a significantly increased risk of adverse events associated with the DMEA treatment.
Benefits from DMEA treatment were found in other studies evaluating DMEA’s ability to increase theta power or concentration.
DMEA has been also used as an ingredient in skin care, and in cognitive function- and mood-enhancing products.
Riker Laboratories’ prescription drug Deaner (Deanol p-acetamidobenzoate) was a U.S. prescription drug for more than 20 years until 1983 when it was withdrawn from the market.
Deaner (deanol p-acetamidobenzoate) was used to treat children with learning and behavior problems.
However, evidence of efficacy was insufficient (Natural Medicines Comprehensive Database, 2002).
In 1959, an Italian article described the use of Deaner in 50 children.
The brief review by CVS Pharmacy (undated) listed the indications for use of Deaner while it was FDA-approved as possibly effective.
The Merck Index, 13th edition, deanol monograph states that Riker’s preparation was patented in 1957.
Remington’s Practice of Pharmacy, 1961 edition 7) listed Deaner as an unofficial (i.e., not listed in the U.S. Pharmacopoeia or the National Formulary) psychomotor stimulant.
Doses of up to 900 mg/day had not been associated with any serious side effects. Oral doses for children with behavior problems were 75 mg/day to start with 75- to 150-mg/day maintenance doses.
Twenty-five years ago, the suggested average daily dose of deanol for adults with Huntington’s chorea was 1.0 to 1.5 g (3.7 to 5.6 mmol) 8).
The anti-inflammatory, analgesic composition Diclofenac-deanol is apparently available in dosages of 75 mg diclofenac and 15 mg deanol (Gerot Pharmazeutica, undated).
DMEA is hypothesized to increase the production of acetylcholine (a chemical that helps nerve cells transmit signals).
Since acetylcholine plays a key role in many brain functions, such as learning and memory, proponents claim that taking DMEA in supplement form may boost brain health by raising acetylcholine levels.1
Recently, a number of synthetic drugs used in a variety of therapeutic indications have been reported to have antiaging effects.
Among them, Dimethylethanolamine (DMEA), an anologue of dietylaminoethanol, is a precursor of choline, which in turn allows the brain to optimize the production of acetylcholine that is a primary neurotransmitter involved in learning and memory.
Biochemical significance
Dimethylethanolamine is related to choline and may be a biochemical precursor to the neurotransmitter acetylcholine, although this conclusion has been disputed based on a 1977 rat experiment.
It is commonly believed that Dimethylethanolamine is methylated to produce choline in the brain, but this has been shown not to be the case (in a rat experiment).
It is known that Dimethylethanolamine is processed by the liver into choline; however, in a rat experiment the choline molecule is charged and cannot pass the blood–brain barrier.
In the brain, DMEA is instead bound to phospholipids in place of choline to produce phosphatidyl-Dimethylethanolamine.
This is then incorporated into nerve membranes, increasing fluidity and permeability, and acting as an antioxidant.
Biomedical research
Short-term studies have shown an increase in vigilance and alertness with a positive influence on mood following administration of DMEA, vitamins, and minerals in individuals suffering from borderline emotional disturbance.
Research for ADHD has been promising, though inconclusive.
A study showed Dimethylethanolamine to decrease the average life span of aged quail.
Three other studies showed an increase in lifespan of mice
The bitartrate salt of DMEA, i.e. 2-Dimethylethanolamine (+)-bitartrate, is sold as a dietary supplement.
It is a white powder providing 37% DMEA.
The Dimethylethanolamine (DMEA) market has been expanding significantly for the last few years. This can be primarily ascribed to a rise in the demand for ion exchange resins, emulsifying agents, and flocculating agent in end-use industries. DMEA acts as a good ingredient and plays an important role in addressing several issues associated with the cleansing and antibacterial properties in the cosmetic industry; hence, it is widely used in skin care products. Demand for urethane catalyst has been rising consistently for the last few years, which in turn is anticipated to boost the demand for DMEA.
Rise in demand for polyurethane is expected to create significant opportunities for urethane catalyst industries. Dimethylethanolamine (DMEA) is an effective, economical amine catalyst for flexible and rigid polyurethane foams. Increase in demand for DMEA as a catalyst in the production of polyurethane foam is expected to create lucrative opportunities for the Dimethylethanolamine (DMEA) market
Translated names
2-(dimethylamino)ethan-1-ol (cs)
2-(dimetylamino)etanol (sk)
2-(dimetyloamino)etanol (pl)
2-dimethylaminoethanol (da)
2-Dimethylaminoethanol (de)
2-dimethylaminoethanol (nl)
2-dimetil-aminoetanol (hr)
2-dimetilaminoetanol (es)
2-dimetilaminoetanol (hu)
2-dimetilaminoetanol (pt)
2-dimetilaminoetanol (ro)
2-dimetilaminoetanol (sl)
2-dimetilaminoetanolis (lt)
2-dimetilaminoetanolo (it)
2-dimetilaminoetanols (lv)
2-dimetylaminoetanol (no)
2-dimetylaminoetanol (sv)
2-dimetyyliaminoetanoli (fi)
2-dimetüülaminoetanool (et)
2-diméthylaminoéthanol N,N-diméthyléthanolamine (fr)
2-διμεθυλαμινοαιθανόλ (el)
2-диметиламиноетанол (bg)
<I>N,N</I>-dimetil-etanolamin (hr)
N,N-dimethylethanolamin (cs)
N,N-Dimethylethanolamin (de)
N,N-dimetiletanolamin (hu)
N,N-dimetiletanolamin (sl)
N,N-dimetiletanolamina (ro)
N,N-dimetiletanolaminas (lt)
N,N-dimetiletanolamīns (lv)
N,N-dimetyletanolamín (sk)
N,N-dimetyloetanoloamina (pl)
N,N-dimetüületanoolamiin (et)
N,N-диметилетаноламин (bg)
CAS names
Ethanol, 2-(dimethylamino)-
IUPAC names
2- Dimethylaminoethanol
2-(Dimethylamino) ethanol
2-(dimethylamino)-ethanol
2-(dimethylamino)ethan-1-ol
2-(Dimethylamino)ethanol
2-(dimethylamino)ethanol
2-(dimethylamino)ethanol
2-Dimethylaminoethanol
2-dimethylaminoethanol
2-Dimethylaminoethanol
2-dimethylaminoethanol
2-dimethylaminoethanol, DMEA
2-dimethylaminoethanol;
2-dimethylaminoethanol; N,N-dimethylethanolamine
Dimethylaminoethanol
DIMETHYLAMINOETHANOL
Dimethylaminoethanol
Dimethylethanolamine
DMEA
DMEA – CM0564B
N,N-Dimethylethanolamine
N,N-dimethylethanolamine
Trade names
(2-Hydroxyethyl)dimethylamine
(Dimethylamino)ethanol
(N,N-Dimethylamino)ethanol
.beta.-(Dimethylamino)ethanol
.beta.-Dimethylaminoethyl alcohol
.beta.-Hydroxyethyldimethylamine
2-(Dimethylamino)-1-ethanol
2-(Dimethylamino)ethanol
2-(N,N-Dimethylamino)ethanol
2-Dimethylaminoethanol (DMEA)
Amietol M 21
Amietol M21
Bimanol
Deanol
Dimethol
Dimethyl(2-hydroxyethyl)amine
Dimethyl(hydroxyethyl)amine
Dimethylethanolamin
Dimethylethanolamine
Dimethylmonoethanolamine
DMEA
DMEA
Ethanol, 2-(dimethylamino)- (8CI, 9CI)
Kalpur P
Liparon
N,N-Dimethyl(2-hydroxyethyl)amine
N,N-Dimethyl-.beta.-hydroxyethylamine
N,N-Dimethyl-2-aminoethanol
N,N-Dimethyl-N-(.beta.-hydroxyethyl)amine
N,N-Dimethyl-N-(2-hydroxyethyl)amine
N,N-Dimethylethanolamine
N-(2-Hydroxyethyl)dimethylamine
Norcholine
Propamine A
Texacat DME
AMIETOL M 21
B-DIMETHYLAMINOETHYL ALCOHOL
BETA-(DIMETHYLAMINO)ETHANOL
BETA-DIMETHYLAMINOETHANOL
BETA-DIMETHYLAMINOETHYL ALCOHOL
BETA-HYDROXYETHYLDIMETHYLAMINE
BIMANOL
DEANOL
DIMETHOL
DIMETHYL(2-HYDROXYETHYL)AMINE
DIMETHYL(HYDROXYETHYL)AMINE
(DIMETHYLAMINO)ETHANOL
2-(DIMETHYLAMINO)ETHANOL
2-(DIMETHYLAMINO)ETHYL ALCOHOL
DIMETHYLAMINOETHANOL
DIMETHYLAMINOETHANOL, [CORROSIVE LIQUID]
2-DIMETHYLAMINOETHANOL
DIMETHYLETHANOLAMINE
DIMETHYLMONOETHANOLAMINE
DMEA
(2-HYDROXYETHYL)DIMETHYLAMINE
KALPUR P
LIPARON
N,N-DIMETHYL(2-HYDROXYETHYL)AMINE
N,N-DIMETHYL-2-AMINOETHANOL
N,N-DIMETHYL-2-HYDROXYETHYLAMINE
N,N-DIMETHYL-BETA-HYDROXYETHYLAMINE
N,N-DIMETHYL-N-(2-HYDROXYETHYL)AMINE
N,N-DIMETHYL-N-(BETA-HYDROXYETHYL)AMINE
(N,N-DIMETHYLAMINO)ETHANOL
2-(N,N-DIMETHYLAMINO)ETHANOL
N,N-DIMETHYLAMINOETHANOL
N,N-DIMETHYLETHANOLAMINE
N-(2-HYDROXYETHYL)DIMETHYLAMINE
N-DIMETHYLAMINOETHANOL
NORCHOLINE
PROPAMINE A
REXOLIN
TEXACAT DME
THANCAT DME
Global Dimethylaminoethanol (DMEA) Market, by Application
Cleansing Agent
Antibacterial Agent
Flocculating Agent
Emulsifying Agent
Ion-Exchange Resin
Epoxy Resin Hardener Ingredient
Global Dimethylethanolamine (DMEA) Market, by End-use
Pharmaceutical
Chemical
Cosmetics
Construction
According to the Organization for Economic Co-operation and Development Screening Information Data Set estimates, 50% of the DMEA produced is used to make flocculants for wastewater treatment, 20% is used in the manufacture of flexible and rigid polyurethane foams and polyurethane lacquers, 20% is used in the manufacture of water-based paints and surface coatings, and the remaining 10% is used for ion exchange resins, pharmaceuticals, and corrosion inhibitor formulations.
DMEA is used for solubilization of water-insoluble resin components for water-based coatings, a process achieved by reaction of DMEA with the resins.
A 2001 article states that DMEA hemisuccinate is used with other chemicals to analyze blood for cholesterol and dehydrocholesterol
DMEA is released into water as a result of its use in the production of polyurethane, acrylates, ion exchange resins and flocculants, and pharmaceuticals.
Based on European estimates, approximately 75% of total DMEA is used in the production of polyurethane, acrylates, ion exchange resins and flocculants, and pharmaceuticals.
While DMEA is cross-linked in the production of polyurethane, resulting in minimal releases to water, up to 50% of the DMEA used in the preparation of ion exchange resins or flocculants may be released to water.
DMEA is also released into the environment as a component of corrosion inhibitor formulations, paints, and surface coatings.
Sealants, architectural coatings, coatings on furniture and cabinets, polyurethane foam cushions, and carpets may emit DMEA in homes, commercial buildings, and vehicles
Industrial uses
Coatings Dimethylethanolamine is used for solubilization of water-insoluble resin components for water-based coatings (ATOFINA Chemicals, Inc., 2000), a process achieved by reaction of Dimethylethanolamine with the resins (Huntsman Corp., 1997).
Water-based Dimethylethanolamine coatings are used on aluminum cans (Dow, 2001a).
In an extensive survey of architectural coatings by the California Air Resources Board (CARB, 1999), Dimethylethanolamine was ranked 77th by weight in a list of 88 ingredients commonly found in waterborne coatings.
It ranked 165th by weight among 186 ingredients used in waterborne or organic-solvent-based coatings.
A recent French study of about 30 water-based paint formulations available to vehiclemanufacturers all contained glycol ethers, N-methylpyrrolidone, [N-methylpyrrolidinone], andalkanolamines (Dimethylethanolamine was mentioned as an example) (Jargot et al., 1999).
Dimethylethanolamine hemisuccinate is named in a patent for organic polymers made from isocyanates to makecathodic electrocoating [Desoto, Inc., U.S.A.] (Lin, 1982), and Dimethylethanolamine bitartrate was part of anaqueous cathodic coating composition to which maleic acid was added to reduce discoloration bymetal ions [PPG Industries, Inc., U.S.A.] (Lucas, 1983).
Dimethylethanolamine is used to produce methacrylatemonomers for polymers as antistatic agents, electrically conducting materials (Huntsman Corp.,1997).
Emulsifying and dispersing agents
Dimethylethanolamine is used as an amino resin stabilizer and as an intermediate in the synthesis of dyes,textiles, and auxiliaries (HSDB, 1996).
Dimethylethanolamine fatty acid soaps are used as emulsifying and dispersing agents for waxes and polishes resistant to water that are used on metal, leather, glass, wood, ceramic ware, floors, furniture, and automobiles, and Dimethylethanolamine esters are common emulsifying agents in the textile industry (Dow, 2001a).
Dimethylethanolamine hydrochloride is used in manufacturing Procter & Gamble detergent compositions (Kandasamy et al., 2000).
Dimethylethanolamine hemisuccinate has been used to make amphoteric surfactants (Nieh and Naylor, 1984).
Gas treating
Alkyl alkanolamines are used to eliminate hydrogen sulfide from natural gas and refinery offgasses (Dow, 2001a). Two out of 73 titles resulting from a CAPLUS search linking Dimethylethanolamine to environmental pollution indicated that Dimethylethanolamine is used to remove hydrogen sulfide from gas mixtures.
Urethane catalysts
Dimethylethanolamine is one of at least 60 amine compounds used as catalysts in the manufacture of polyurethane and polyisocyanurate foams.
Polyurethane formulations require about 0.1 to 5.0% amine catalyst (API, 2000).
Dimethylethanolamine reacts with isocyanates, limiting the amount of Dimethylethanolamine emissions during the foaming reaction (Dow, 2001a).
One study evaluated amine catalyst use in polyurethane production in the United Kingdom.
At afactory making polyether slabstock, the “typical total throughput” of chemicals was 300 kg perminute: 200 kg polyol per minute, 100 kg per minute 80:20 diisocyanates, and 0.6 kg/minuteamine.
At a typical factory for making polyester slabstock, with a throughput of 300 kg perminute, 0.5 to 1.5 kg per minute would be used.
At a typical factory for making a molding, theestimated throughput was 12 kg per minute and the rate of amine use was 0.02 kg per minute(Bugler et al., 1992).
Dimethylethanolamine in vapor phase is also used to catalyze polyurethane-based inks(Huntsman Corp., 1997) to catalyze coatings (U.S. EPA ORD, 1994), and for curing epoxyresins (HSDB, 1996). API (2000) lists 55 other amine catalysts used in polyurethane manufacture.
The di-Dimethylaminoethanolether, that is, bis(2-dimethylaminoethyl) ether [CAS RN 3033-62-3] may be the most widelyused amine catalyst in polyurethane manufacture.
Water treatment
Dimethylethanolamine is used to make flocculants for wastewater treatment (Dow, 2001a; Huntsman Corp.,1997), to inhibit corrosion in return-condensate boiler and steam systems by controlling pH (Dow, 2001a; HSDB, 1996), and to synthesize Type II resins for anion exchange (Dow, 2001a).
Other industrial uses
Other uses of Dimethylethanolamine include as a chemical intermediate (HSDB, 1996), as a corrosion inhibitorin steel-reinforced concrete (CCIA, undated; FHWA DOT, 2000), and as “paper auxiliaries”(Huntsman Corp., 1997).
N,N-Dimethylethanolamine S
N,N-Dimethylethanolamine S (DMEOA, DMEA) belongs to the class of N-alkylated aminoalcohols.
DMEOA is a colorless to slightly yellow liquid with a amine-like odor.
Coatings
DMEOA is used as an intermediate + buffering agent in the synthesis of coatings.
Other
DMEOA is used as a building block for the synthesis of cationic flocculants and ion exchange resins.
Dimethylethanolamine toxicology
Dimethylethanolamine is absorbed and rapidly transported to the liver where much of it is metabolized 33).
Approximately 280 nmol (25.2 μg) Dimethylethanolamine/gram plasma was observed in male mice about ten minutes after receiving 300 mg (3.30 mmol) Dimethylethanolamine/kg, intraperitoneally. Approximately 2.41, 1.30, and 0.20% of an administered dose of 30 mg/kg (0.13 mmol/kg) (with 100 μCi) of 14Ccyprodenate was found in the liver, brain, and plasma, respectively, five minutes after intravenous dosing in male rats. After transport to the liver, a portion of centrophenoxine was converted to its constituent moieties, Dimethylethanolamine and p-chlorophenoxyacetic acid, while the unmetabolized form was transported throughout the body by the circulatory system.
Daily Dimethylethanolamine oral exposures of chinchilla rabbits or humans produced measurable plasma and cerebrospinal concentrations of the parent compound.
The drugs were cleared from the plasma by 36 hours post-treatment.
In male Wistar rats, Dimethylethanolamine was oxidized rapidly to the N-oxide of Dimethylethanolamine, representing the primary urinary metabolite.
However, only 13.5 % of the administered dose was eliminated by the 24 hour time point, suggesting that most of the Dimethylethanolamine was routed toward phospholipid biosynthetic pathways.
In humans, 33% of an injected 1 g (10 mmol) dose of Dimethylethanolamine was excreted unchanged.
It was suggested that the remaining dose might have been demethylated to ethanolamine directed toward normal metabolic pathways.
It is unclear to what extent Dimethylethanolamine is methylated and substituted into acetylcholine.
Some reports indicated that the Dimethylethanolamine that crossed the blood-brain barrier was methylated to form choline and then incorporated into acetylcholine.
Other investigators found that neither acute (in vitro) nor chronic (in vivo) treatments with [2H6] Dimethylethanolamine had the capacity to alter levels of acetylcholine in the brain tissues.
Choline may be formed by methylation of Dimethylethanolamine. De novo synthesis of choline typically involves conversion of phosphatidylethanolamine to phosphatidylcholine.
lthough small amounts may be synthesized, choline must be supplemented through the diet to maintain adequate physiological concentrations for optimal health.
Most of the body’s choline is found as a component of phospholipids.
Choline-containing phospholipids, especially phosphatidylcholine and sphingomyelin, are structural components of cell membranes and precursors for intracellular messenger molecules.
Phosphatidylcholine is a required component of very low-density lipoprotein (VLDL) particles, necessary for the transportation of cholesterol and fat from the liver to other sites in the body. Finally, choline is a precursor for the neurotransmitter, acetylcholine.
As a possible precursor of choline, Dimethylethanolamine has been studied as a potential modulator of many of the above-mentioned biological processes 34).
Dimethylethanolamine acute exposures
Lethal concentration 50 (LC50) is the concentration of the chemical in the air or water that will kill 50% of the test animals with a single exposure.
Dimethylethanolamine inhalation studies resulted in lethal concentration 50 (LC50) values in the mouse of 36.14 mmol/m³.
The upper range for the rat was reported at 70 mmol/m³.
Lethal dose 50 (LD50) is a single dose of a chemical that, when fed, injected or applied to the skin test animals, will kill 50% of the animals.
The LD50 is one way to measure the short-term poisoning potential (acute toxicity) of a material.
Oral Dimethylethanolamine LD50s ranged from 6.790 to 14.60 mmol/kg (mouse) to 2.94 to 67.31 mmol/kg (rat).
Skin Dimethylethanolamine LD50s were derived only for rabbits and ranged from 13.5 to 34.86 mmol/kg.
Signs of toxicity from inhalation exposures included irritation to the mucous membranes of the eyes and upper respiratory tract and incoordination; abnormal contraction of the eyelid muscles and excessive secretion of tears; excessive salivation; ocular, oral, and nasal discharge and encrustation; respiratory difficulties; decreased motor activity; coordination loss, and swelling and bleeding of extremities from excessive preening (high-dose only); and a substantial body-weight loss 35). Discolored lungs, liver, kidneys, and spleen were observed in rats that died and in two high-dose survivors.
Dimethylethanolamine, classified as corrosive (occlusive or semi-occlusive dressings), was moderately lethal in rabbits after acute percutaneous exposures.
Moderate to severe erythema and edema with ecchymoses, necrosis, and ulceration occurred after Dimethylethanolamine application for 24 hours, and progressed to local desquamation, alopecia, and scarring.
Application of 0.75 mg (0.0083 mmol) Dimethylethanolamine to the eyes of rabbits produced severe irritation.
Moderate to severe corneal injury, iritis, and severe conjunctival irritation (with necrosis) was observed in all rabbits treated with 0.005 mL (4 mg; 0.05 mmol) Dimethylethanolamine.
Dimethylethanolamine short-term exposures
All Dimethylethanolamine high-dose (586 ppm; 24 mmol/m³) rats died between days four through eight, and four of fifteen mid-dose (288 ppm; 11.8 mmol/m³) males died on days eight through twelve after inhalation exposure to Dimethylethanolamine (six hours/day, five days/week, nine exposures in eleven days) 36).
Signs of toxicity included respiratory distress, ocular and nasal irritation, and corneal opacity.
Male and female New Zealand White rabbits treated dermally with Dimethylethanolamine (up to 2.0 mL/kg/day (1800 mg/kg/day; 20 mmol/kg/day) developed severe skin irritation.
Microscopic examination revealed no treatmentrelated effects in regions other than treated skin.
Male Wistar rats (24-month-old) dosed orally with centrophenoxine (100 mg/kg body weight [0.640 mmol/kg]) once a day for four weeks had significant differences in malondialdehyde, phospholipid content, superoxide dismutase activity, glutathione and protein thiol relative to tissue levels from untreated young and old rats.
Dimethylethanolamine subchronic and chronic exposures
Male and female rats exposed to Dimethylethanolamine (8 to 76 ppm; 0.3 to 3.1 mmol/m³, six hours/day, five days/week, thirteen weeks) produced corneal opacity in mid- and high-dose rats; an increase in audible respiration was demonstrated in the high-dose group 37).
Histopathologic changes in nasal tissue were observed, including rhinitis, squamous metaplasia, degeneration of respiratory epithelium, atrophy of olfactory epithelium, and microcysts in respiratory epithelium. Nasal lesions were limited to the anterior nasal cavity.
Chronic exposures of mice to emissions from freshly foamed polyurethane insulation [6.7 mg/m³ Dimethylethanolamine (0.075 mmol/m³)] produced disturbances in blood composition including increased leukocyte count and decrease in erythrocytes and hemoglobin content.
A decrease in plasma triglyceride and cholesterol was observed in rats receiving 10 mg/kg (0.10 mmol/kg) per day Dimethylethanolamine orotate for six months, without any signs of fatty acid infiltration of the liver.
A four-month continuous inhalation exposure of rats to high concentrations of Dimethylethanolamine (2.76 mg/m3; 0.031 mmol/m³) resulted in a disturbance in the “dynamic equilibrium between processes of inhibition and excitation” with “prevalence for excitation.”
No-Observed-Adverse-Effect Level (NOAEL) denotes the level of exposure of an organism, found by experiment or observation, at which there is no biologically or statistically significant increase in the frequency or severity of any adverse effects of the tested protocol.
A 90-day Dimethylethanolamine feeding study resulted in a NOAEL 180 mg (2 mmol) Dimethylethanolamine/kg.
The Lowest-Observed-Adverse-Effect Level (LOAEL) is the lowest concentration or amount of a substance found by experiment or observation that causes an adverse alteration of morphology, function, capacity, growth, development, or lifespan of a target organism distinguished from normal organisms of the same species.
The LOAEL of Dimethylethanolamine is 890 mg (10 mmol) Dimethylethanolamine/kg 38).
Dimethylethanolamine reproductive and teratological effects
No histopathological changes in the gonads were observed after repeated exposure to Dimethylethanolamine in a 90 day inhalation study in rats 39).
Dimethylethanolamine induced maternal toxicity as demonstrated by changes in body weight gain in the mid- and high-dose (30 and 100 ppm; 1.20 and 4.10 mmol/m³) groups and ocular changes in the mid- and low dose groups (30 and 10 ppm; 1.20 and 0.41 mmol/m³).
Sporadic, inconsistent alterations in gestational parameters included significant decreases in viable implants per litter, percentage live fetuses/litter, and litter size in rats exposed to 10 ppm (40mg/m³; 41 mmol/m³).
A significant decrease in the percentage of male fetuses in rats exposed to 30 ppm (1.20 mmol/m³) was reported.
Inhaled Dimethylethanolamine induced an inconsistent pattern of skeletal variations reported as poorly ossified cervical centrum, bilobed thoracic centrum, bilobed sternebrae, unossified proximal phalanges of the forelimb, and increased incidences of split cervical centra, and bilobed thoracic centrum.
A NOAEL (No-Observed-Adverse-Effect Level) of 100 ppm (4.10 mmol/m³) or greater was established for embryofetal toxicity and teratogenicity.
A NOAEL for maternal toxicity was estimated at 10 ppm (0.41 mmol/m³).
Pups derived from pregnant rats dosed with Dimethylethanolamine (gestation day 12 through postnatal day 10) demonstrated diminished behavioral decrements (motor activity in the pups; striatal dopamine release in adults) induced by postnatal hypoxia.
Dimethylethanolamine and immunotoxicity
Immunotoxicity is defined as adverse effects on the functioning of both local and systemic immune systems that result from exposure to toxic substances.
Dimethylethanolamine has been classified as a potential skin sensitizer, although this classification has not been supported by human experiences with Dimethylethanolamine under normal handling procedures.
A sensitizer is defined as “a chemical that causes a substantial proportion of exposed people or animals to develop an allergic reaction in normal tissue after repeated exposure to the chemical.” Dimethylethanolamine, evaluated in the guinea pig maximation test was without any clear evidence of skin sensitization 40).
Dimethylethanolamine and the formation of cancer
There was no statistically significant increase, or morphological difference, in the incidence of neoplasms in any organ in female mice given drinking water with 10 mM (900 μg/mL) Dimethylethanolamine for 105 weeks, or in female mice given 15 mM (1300 μg/mL) Dimethylethanolamine for 123 weeks 41).
Dimethylethanolamine and genotoxicity
In genetics, genotoxicity describes the property of chemical agents that damages the genetic information within a cell causing mutations, which may lead to cancer.
Dimethylethanolamine failed to demonstrate genotoxicity in the Salmonella typhimurium assay, Drosophila melanogaster sex-linked recessive lethal assay, sister chromatid exchange assays, or hypoxanthineguanine phosphoribosyl transferase forward gene mutation tests.
No significant increases in the incidence of micronucleated polychromatic erythrocytes were observed in Swiss-Webster mice at Dimethylethanolamine dose levels ranging from 270 to 860 mg/kg body weight (3.00 to 9.60 mmol/kg) 42).
Dimethylethanolamine and choline
Choline has recently been identified as an essential human nutrient, used in the biosynthesis of the phospholipids, phosphatidylcholine, and sphingomyelin and as a precursor of intracellular messenger molecules.
Perturbations in choline metabolism will affect a range of cellular structures and functions.
Dimethylethanolamine (200 μM for 20 minutes) was found to be a potent inhibitor of choline uptake in vitro.
Dimethylethanolamine acted as a choline oxidase inhibitor 43).
In isolated perfused kidney studies, Dimethylethanolamine significantly decreased both the rate of [14C] choline removal and the rate of [14C] betaine addition to the perfusate. Dimethylethanolamine also significantly inhibited [14C] betaine production in cortical, outer, and inner medullary regions of rat kidney in tissue slice experiments.
Although pregnancies progressed equally well for all treatment groups and litters of similar sizes were delivered, only 18/253 offspring derived from pregnant rats maintained on a choline-deficient diet supplemented with 1% Dimethylethanolamine survived for more than 36 hours postpartum.
The pups demonstrated moderate degrees of glycogen and fatty infiltrations in their livers.
Measurable amounts of Dimethylethanolamine (72.2 ± 12.7 nmol/g) were observed in their brains.
In addition, levels of choline and acetylcholine in the brains were elevated 53% and 36%, respectively.
One study reported that the Dimethylethanolamine-induced perturbations of choline uptake and metabolism causedneural tube defects and craniofacial hypoplasia in neurulating mouse embryos in vitro.
Incubation ofmouse embryos for 26 hours in Dimethylethanolamine-containing medium resulted in a statistically significant, dosedependent increase in malformation rate and severity.
Dimethylethanolamine-treatment reduced choline uptake by70% in the 375 μM group (33.7 μg/mL).
Follow-on studies conducted in gastrulation/neurulationstage mouse embryos suggested that Dimethylethanolamine decreased [14C] choline incorporation intophosphocholine, phosphatidylcholine, and sphingomyelin to 25%, 35%, and 50% of control values,respectively, and increased the levels of labeled betaine was threefold.
Dimethylethanolamine treatment produced a15% increase in embryonic ceramide, an important cell-signaling molecule.
Dimethylethanolamine supplement
Dimethylethanolamine salts such as p-acetamidobenzoate (Deanol, Deaner or Pabenol) have been used in humans to treat central nervous system disorders believed to be associated with hypofunction of cholinergic neurons; in the treatment of learning and behavioral problems; hyperkinetic behavior 44); Huntington’s chorea, tardive and levodopa-induced dyskinesias 45); chronic fatigue; and neurasthenia 46).
Dimethylethanolamine salts (Deaner) was recommended for treating schizoid and schizophrenic patients in a 1958 article in the American Journal of Psychiatry 47). Salomon et al. 48) described a clinical trial of Dimethylethanolamine monophosphate (Panclar), described as a psychostimulant, in a neuropsychiatric clinic.
Meclofenoxate hydrochloride (centrophenoxine hydrochloride) is used to enhance cognition in the elderly in Europe, Japan, Mexico and Australia 49). Dimethylethanolamine p-chlorophenoxyacetate and its hydrochlorides (centrofenoxine, meclofenoxate) were named in a review article as showing some efficacy in treating brain injuries, including cerebral atrophy, brain injury, postapopletic disorder, chronic alcoholism, and barbituate intoxications 50), 51).
The Life Extension Foundation Web site (2002a, 2002b) states that in Europe, centrofenoxine in combination with piracetam may improve memory and mental energy.
The article states that the drug is not available in the United States but may be ordered from pharmacies in Europe.
The Giampapa Institute (2001) Web site lists health claims for centrofenoxine that include improving memory, increasing mental energy, removing lipofuscin and potassium from the skin, heart, and brain, and protecting the brain against free radical damage, stroke, and injury.
Dimethylethanolamine and related compounds are found in drug formulations for various purposes.
Dimethylethanolamine was probably one of the basic amines for self-emulsifying oral preparations of antiretroviral pyranones containing 0.1 to 10% basic amines to enhance bioavailability in a World patent assigned to Pharmacia and Upjohn Co., U.S.A 52).
Meclofenoxate was in formulations in a German patent for “transdermal or transmucosal dosage forms containing nicotine for smoking cessation” [LTS Lohmann Therapie-Systeme A.-G., Germany] 53).
Deanol is commonly referred to as 2-(dimethylamino)ethanol, Dimethylethanolamine (DMEA) or dimethylethanolamine (DMEA).
Dimethylethanolamine (DMEA) holds tertiary amine and primary alcohol groups as functional groups.
Deanol has been used in the treatment of attention deficit-hyperactivity disorder (ADHD), Alzheimer’s disease, autism, and tardive dyskinesia.
Dimethylethanolamine (DMEA) has been also used as an ingredient in skin care, and in cognitive function- and mood-enhancing products.
2-Dimethylethanolamine appears as a clear colorless liquid with a fishlike odor. Flash point 105°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used to make other chemicals.
Deanol is commonly referred to as 2-(dimethylamino)ethanol, Dimethylethanolamine (DMEA) or dimethylethanolamine (DMEA). It holds tertiary amine and primary alcohol groups as functional groups. Deanol has been used in the treatment of attention deficit-hyperactivity disorder (ADHD), Alzheimer’s disease, autism, and tardive dyskinesia. It has been also used as an ingredient in skin care, and in cognitive function- and mood-enhancing products.
DrugBank
2-Dimethylethanolamine appears as a clear colorless liquid with a fishlike odor. Flash point 105°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used to make other chemicals.
CAMEO Chemicals
N,N-dimethylethanolamine is a tertiary amine that is ethanolamine having two N-methyl substituents. It has a role as a curing agent and a radical scavenger. It is a tertiary amine and a member of ethanolamines.
Astyl
Bisorcate, Deanol
Deanol
Deanol Bisorcate
Demanol
Demanyl
Dimethylethanolamine
Dimethylethanolamine
N,N Dimethyl 2 hydroxyethylamine
N,N-Dimethyl-2-hydroxyethylamine
N,N-Dimethylethanolamine
Tonibral
Medical Subject Headings (MeSH)
3.4.2Depositor-Supplied Synonyms HelpNew Window
2-(Dimethylamino)ethanol
Deanol
N,N-Dimethylethanolamine
108-01-0
Dimethylethanolamine
Dimethylethanolamine
Norcholine
2-DIMETHYLAMINOETHANOL
DMEA
DMEA
Bimanol
Liparon
N,N-Dimethylaminoethanol
Varesal
Propamine A
Ethanol, 2-(dimethylamino)-
(2-Hydroxyethyl)dimethylamine
Kalpur P
Dimethylmonoethanolamine
Dimethylaminoaethanol
N,N-Dimethyl-2-aminoethanol
Amietol M 21
N,N-Dimethyl-2-hydroxyethylamine
N,N-Dimethyl ethanolamine
N-Dimethylaminoethanol
2-(N,N-Dimethylamino)ethanol
Dimethyl(hydroxyethyl)amine
Texacat DME
Dimethylaethanolamin
Dimethyl(2-hydroxyethyl)amine
2-(Dimethylamino)-1-ethanol
N-(2-Hydroxyethyl)dimethylamine
N,N-Dimethyl-N-(2-hydroxyethyl)amine
2-(Dimethylamino) ethanol
(Dimethylamino)ethanol
beta-Hydroxyethyldimethylamine
2-(dimethylamino)ethan-1-ol
2-Dimethylamino-ethanol
beta-Dimethylaminoethyl alcohol
2-Dwumetyloaminoetanolu
N-(Dimethylamino)ethanol
N,N-Dimethyl-N-(beta-hydroxyethyl)amine
Tegoamin DMEA
NSC 2652
Dabco DMEA
UNII-2N6K9DRA24
Deanol [BAN]
2-Dimethylamino ethanol
N,N-Dimethyl(2-hydroxyethyl)amine
N,N’-Dimethylethanolamine
2-(dimethylamino)-ethanol
(CH3)2NCH2CH2OH
CHEMBL1135
.beta.-(Dimethylamino)ethanol
2N6K9DRA24
.beta.-Hydroxyethyldimethylamine
CHEBI:271436
Phosphatidyl-N-dimethylethanolamine
Deanol (BAN)
MFCD00002846
N,N-DIMETHYLAMINOETHANOL (DMAE)
NCGC00159413-02
Demanol
Demanyl
Tonibral
N,N-Dimethyl-N-(.beta.-hydroxyethyl)amine
DSSTox_CID_505
DSSTox_RID_75628
DSSTox_GSID_20505
N,N-Dimethylethanolamine (2-Dimethylaminoethanol)
Deanol (N,N-Dimethylethanolamine)
CAS-108-01-0
Dimethylaethanolamin [German]
Dimethylamino ethanol
Dimethylaminoaethanol [German]
CCRIS 4802
2-Dwumetyloaminoetanolu [Polish]
HSDB 1329
EINECS 203-542-8
UN2051
BRN 1209235
N,N-Dimethyl-N-ethanolamine
AI3-09209
Jeffcat DMEA
Dimethylethanoiamine
Toyocat -DMA
dimethyl ethanolamine
dimethyl-ethanolamine
Paresan (Salt/Mix)
dimethyl ethanol amine
2-dimethyamino-ethanol
n,n-dimethylethanolamin
Biocoline (Salt/Mix)
N,N dimethylaminoethanol
N,N-dimethyl-ethanolamine
N,N-dimethylamino ethanol
N,N-dimethylethanol amine
N,N-dimethylethanol-amine
ACMC-1C0DD
2-Hydroxyethyldimethylamine
2-Dimethylaminoethanol [UN2051] [Corrosive]
EC 203-542-8
beta -(dimethylamino)ethanol
Dimethylaminoaethanol(german)
Choline chloride (Salt/Mix)
Luridin chloride (Salt/Mix)
beta -hydroxyethyldimethylamine
N,N-Dimethylethanolamine/DMEA
beta -dimethylaminoethyl alcohol
2-(N,N-dimethyl amino)ethanol
2-(N,N-dimethylamino) ethanol
DTXSID2020505
N-hydroxyethyl-N,N-dimethylamine
.beta.-Dimethylaminoethyl alcohol
2-(N,N-dimethyl amino) ethanol
Ni(1/4)OEN-Dimethylethanolamine
NSC2652
beta -(dimethylamino)ethyl alcohol
2-hydroxy-N,N-dimethylethanaminium
WLN: Q2N1 & 1
2-Dimethylaminoethanol, >=99.5%
BCP22017
CS-M3462
NSC-2652
ZINC1641058
.beta.-(Dimethylamino)ethyl alcohol
N, N-Dimethyl(2-hydroxyethyl)amine
BDBM50060526
N,N-Dimethyl-beta -hydroxyethylamine
STL282730
Dimethylaminopropylamine Reagent Grade
AKOS000118738
N,N-Dimethyl-.beta.-hydroxyethylamine
DB13352
MCULE-7567469160
UN 2051
N, N-Dimethyl-N-(2-hydroxyethyl)amine
IUPAC Name
2-(dimethylamino)ethanol
Synonyms
(2-Hydroxyethyl)dimethylamine
2-(Dimethylamino)-1-ethanol
2-(N,N-Dimethylamino)ethanol
2-Dimethylaminoethanol
beta-Dimethylaminoethyl alcohol
beta-Hydroxyethyldimethylamine
Deanol
Dimethyl(2-hydroxyethyl)amine
Dimethyl(hydroxyethyl)amine
Dimethylaminoäthanol Deutsch
Dimethyläthanolamin Deutsch
Dimethylethanolamine
Dimethylmonoethanolamine
DMAE
DMEA
N,N-Dimethyl-2-aminoethanol
N,N-Dimethyl-2-hydroxyethylamine
N,N-Dimethyl-N-(2-hydroxyethyl)amine
N,N-Dimethyl-N-(beta-hydroxyethyl)amine
N,N-Dimethylaminoethanol
N,N-Dimethylethanolamine
N,N-dimethylethanolamine
N-(2-Hydroxyethyl)dimethylamine
N-Dimethylaminoethanol
Norcholine
Propamine A
Synonyms
Deanol; (2-Hydroxyethyl)dimethylamine; 2-(Dimethylamino)-1-ethanol; 2-(N,N-Dimethylamino)ethanol; 2-Dimethylaminoethanol; 2-Dwumetyloaminoetanolu [Polish]; Amietol M 21; Bimanol; DMAE; DMEA; Deanol; Dimethyl(2-hydroxyethyl)amine; Dimethyl(hydroxyethyl)amine; Dimethylaethanolamin [German]; Dimethylaminoaethanol [German]; Dimethylaminoethanol; Dimethylethanolamine; Dimethylmonoethanolamine; Ethanol, 2-(dimethylamino)-; Kalpur P; Liparon; N,N-Dimethyl-2-aminoethanol; N,N-Dimethyl-2-hydroxyethylamine; N,N-Dimethyl-N-(2-hydroxyethyl)amine; N,N-Dimethyl-N-(beta-hydroxyethyl)amine; N,N-Dimethylaminoethanol; N,N-Dimethylethanolamine; N-(2-Hydroxyethyl)dimethylamine; N-Dimethylaminoethanol; Norcholine; Propamine A; Texacat DME; Varesal; beta-Dimethylaminoethyl alcohol; beta-Hydroxyethyldimethylamine; [ChemIDplus] UN2051; UN2920
108-01-0 [RN]
1209235 [Beilstein]
2-(Dimethylamino)-1-ethanol
2-(Dimethylamino)ethanol [ACD/IUPAC Name]
2-(Dimethylamino)ethanol [German] [ACD/IUPAC Name]
2-(Diméthylamino)éthanol [French] [ACD/IUPAC Name]
203-542-8 [EINECS]
2-DIMETHYLAMINOETHANOL
2-Dwumetyloaminoetanolu [Polish]
2N6K9DRA24
4-11-00-00122 [Beilstein]
Deanol [Wiki]
Dimethyl(2-hydroxyethyl)amine
Dimethyl(hydroxyethyl)amine
Dimethylaethanolamin [German]
Dimethylaminoaethanol [German]
DMAE
DMEA
Ethanol, 2-(dimethylamino)- [ACD/Index Name]
KK6125000
MFCD00002846 [MDL number]
N-(2-Hydroxyethyl)dimethylamine
N,N-Dimethyl-2-aminoethanol
N,N-Dimethyl-2-hydroxyethylamine
N,N-Dimethylethanolamine
N,N-Dimethyl-N-(2-hydroxyethyl)amine
N,N-Dimethyl-N-(β-hydroxyethyl)amine
UNII-2N6K9DRA24
β-Dimethylaminoethyl alcohol
β-Hydroxyethyldimethylamine
(2-Hydroxyethyl)dimethylamine
(CH3)2NCH2CH2OH
(Dimethylamino)ethanol
116134-09-9 alternate RN [RN]
2-(Dimethylamino) ethanol
2-(dimethylamino)ethan-1-ol
2-(Dimethylamino)-ethanol
2-(N,N-Dimethylamino)ethanol
2-Dimethylamino ethanol
2-Dimethylamino-ethanol
Amietol M 21 [Trade name]
Bimanol [Trade name]
Demanol [Trade name]
Dimethylaminoethanol [Wiki]
Dimethylethanoiamine
Dimethylethanolamine [Wiki]
Dimethylmonoethanolamine
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:271436
Kalpur P [Trade name]
Liparon [Trade name]
N-(Dimethylamino)ethanol
N, N-Dimethylethanolamine
N,N-Dimethyl ethanolamine
N,N-Dimethyl(2-hydroxyethyl)amine
N,N-dimethylaminoethanol
N,N’-Dimethylethanolamine
N,N-Dimethyl-N-(β -hydroxyethyl)amine
N,N-Dimethyl-N-(β-hydroxyethyl)amine
N,N-Dimethyl-N-ethanolamine
N,N-Dimethyl-N-ethanolamine.
N,N-Dimethyl-β -hydroxyethylamine
N,N-Dimethyl-β-hydroxyethylamine
N-Benzyloxycarbonyl-L-tyrosine
N-dimethyl aminoethanol
N-Dimethylaminoethanol
Norcholine [Trade name]
Propamine A [Trade name]
Q2N1 & 1 [WLN]
Texacat DME [Trade name]
UN 2051
Varesal [Trade name]
β -(dimethylamino)ethanol
β -(dimethylamino)ethyl alcohol
β -dimethylaminoethyl alcohol
β -hydroxyethyldimethylamine
β-(Dimethylamino)ethanol
β-(Dimethylamino)ethyl alcohol
β-Dimethylaminoethyl alcohol
β-Hydroxyethyldimethylamine
Other names: N,N-Dimethyl-2-aminoethanol; Deanol; Varesal; Bimanol; Ethanol, 2-(dimethylamino)-; β-(Dimethylamino)ethanol; β-(Dimethylamino)ethyl alcohol; β-Hydroxyethyldimethylamine; (Dimethylamino)ethanol; (2-Hydroxyethyl)dimethylamine; Dimethyl(hydroxyethyl)amine; Dimethyl(2-hydroxyethyl)amine; Dimethylethanolamine; Dimethylmonoethanolamine; DMAE; Kalpur P; Liparon; N-(2-Hydroxyethyl)dimethylamine; N,N-Dimethyl(2-hydroxyethyl)amine; N,N-Dimethyl-N-(β-hydroxyethyl)amine; N,N-Dimethyl-N-(2-hydroxyethyl)amine; N,N-Dimethylethanolamine; Norcholine; Propamine A; 2-(Dimethylamino)ethanol; 2-(N,N-Dimethylamino)ethanol; (CH3)2NCH2CH2OH; Amietol M 21; Dimethylaminoaethanol; N-(Dimethylamino)ethanol; 2-(Dimethylamino)-1-ethanol; Dimethylaethanolamin; UN 2051; N,N-Dimethyl-β-hydroxyethylamine; Dabco DMEA; N,N’-Dimethylethanolamine; Tegoamin DMEA; Texacat DME; DMEA; NSC 2652; 67-48-1
Dimethylaminoethanol, 2-
2-(dimethylamino)ethanol, N,N-dimethylethanolamine, amietol M 21, Bimanol, Deanol, Liparon, Kalpur B, Norchlorine, Propamine A, Texacat DME, N,N-dimethyl-2-aminoethanol, Varesal, ethanol, 2-(dimethylamino)-, ß-(dimethylamino)ethanol, ß-(dimethylamino)ethyl alcohol, ß-hydroxyethyldimethylamine, (dimethylamino)ethanol, (2-hydroxyethyl)dimethylamine, dimethyl(hydroxyethyl)amine, dimethyl(2-hydroxyethyl)amine, dimethylethanolamine, dimethylmonoethanolamine, N-(2-hydroxyethyl)dimethylamine, DMAE, N,N-dimethyl(2-hydroxyethyl)amine, N,N-dimethyl-N-(ß-hydroxyethyl)amine, N,N-dimethyl-N-(2-hydroxyethyl)amine, N,N-dimethylethanolamine, Norcholine, Propamine A, 2-(dimethylamino)ethanol, 2-(N,N-dimethylamino)ethanol, dimethylaminoaethanol, N-(dimethylamino)ethanol, 2-(dimethylamino)-1-ethanol, N,N-dimethyl-ß-hydroxyethylamine, N,N’-dimethylethanolamine
Uses
dimethyl MEA (DMAE) is also known as dimethylaminoethanol. Studies indicate skin-firming properties, and an ability to reduce the appearance of fine lines and wrinkles as well as dark circles under the eyes. It is considered anti-aging, and antiinflammatory, and has exhibited free-radical scavenging activity.
Uses
2-(Dimethylamino)ethanol is used as corrosion inhibitor, anti-scaling agent, paint additive, coating additive and solids separation agent. It is also used as an intermediate for active pharmaceutical ingredients and dyes. It serves as a curing agent for polyurethanes and epoxy resins. Further, it is used as an additive to boiler water. In addition to this, it is used therapeutically as a CNS stimulant.
Definition
ChEBI: A tertiary amine that is ethanolamine having two N-methyl substituents.
Production Methods
Synthesis of dimethylaminoethanol can be accomplished from equimolar amounts of ethylene oxide and dimethylamine (HSDB 1988).
General Description
A clear colorless liquid with a fishlike odor. Flash point 105°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used to make other chemicals.
Air & Water Reactions
Flammable. Partially soluble in water and less dense than water.
Reactivity Profile
DIMETHYLAMINOETHANOL is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water.
These acid-base reactions are exothermic.
The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base.
Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
N,N-Dimethylethanolamine may react vigorously with oxidizing materials.
Health Hazard
Inhalation of the vapor or mist can cause irritation to the upper respiratory tract. Asthmatic symptoms have been reported.
Extremely irritating; may cause permanent eye injury. Corrosive; will cause severe skin damage with burns and blistering.
Ingestion may cause damage to the mucous membranes and gastrointestinal tract.
Health Hazard
Dimethylaminoethanol is classified as a mild skin irritant and a severe eye irritant (HSDB 1988).
Doses as high as 1200 mg daily produce no serious side effects and a single dose of 2500 mg taken in a suicide attempt had no adverse effects (Gosselin et al 1976).
Reported side effects for the acetamidobenzoate salt of dimethylaminoethanol include occipital headache, constipation, muscle tenseness, restlessness, increased irritability, insomnia, pruritus, skin rash, postural hypotension, and weight loss (HSDB 1988).
Under laboratory conditions, asthmatic responses resulted after exposure to a 2% dimethylaminoethanol solution to a spray painter who earlier was exposed to a similar concentration of dimethylaminoethanol via a particular paint (Vallieres et al 1977).
Serious cholinergic side effects were reported in a 37 yr-old woman with tardive dyskinesia who had been taking dimethylaminoethanol (Nesse and Carroll 1976).
After chronic treatment (5 months) with dimethylaminoethanol, marked sialism, bronchospasm, and parkinson rigidity was observed in an 89 yr-old male with a 50 yr history of chronic paranoid schizophrenia and symptoms of tardive dyskinesia (Mathew et al 1976).
Dimethylaminoethanol appears to have a relatively low order of toxicity (HSDB 1988).
Upon chronic administration in humans, plasma choline concentrations were found to be increased (Ceder et al 1978).
No reports were found in the literature regarding carcinogenic or mutagenic potential.
Industrial uses
Dimethylaminoethanol is used as a chemical intermediate for antihistamines and local anesthetics; as a catalyst for curing epoxy resins and polyurethanes; and as a pH control agent for boiler water treatment.
However, dimethylaminoethanol in the salt form, (i.e. dimethylaminoethanol acetamidobenzoate) is primarily utilized therapeutically as an antidepressant (HSDB 1988).
Safety Profile
Moderately toxic by ingestion, inhalation, skin contact, intraperitoneal, and subcutaneous routes.
A skin and severe eye irritant. Used medically as a central nervous system stimulant.
Flammable liquid when exposed to heat or flame; can react vigorously with oxidzing materials.
Ignites spontaneously in contact with cellulose nitrate of high surface area. To fight fire, use alcohol foam, foam, CO2, dry chemical.
When heated to decomposition it emits toxic fumes of NOx
Metabolism
When administered orally, dimethylaminoethanol acetamidobenzoate (the therapeutic salt formulation) has been shown to cross the blood-brain barrier (HSDB 1988).
Two other studies have examined the pharmacokinetics of dimethylaminoethanol in rats (Dormand et al 1975) and healthy adults (Bismut et al 1986).
It has been postulated that dimethylaminoethanol undergoes endogenous methylation (LaDu et al 1971).
After intravenous treatment of mice with [14C]-labeled dimethylaminoethanol in the brain, dimethylaminoethanol yielded phosphoryldimethylaminoethanol and phosphatidyldimethylaminoethanol. Acid-soluble and lipid cholines derived from dimethylaminoethanol also were found in brain (Miyazaki et al 1976).
While examining the pharmacokinetics of the maleate acid of [14C]-dimethylaminoethanol in rats, Dormand et al (1975) observed that dimethylaminoethanol was metabolized in the phospholipid cycle and produced metabolites such as phosphoryldimethylaminoethanolamine, and glycerophosphatidylcholine.
In kainic-acid lesioned rats, dimethylaminoethanol was converted to a substance which cross-reacted in the radioenzymatic assay for acetylcholine (London et al 1978).
Ansell and Spanner (1979) demonstrated that [14C]-dimethylaminoethanol rapidly disappeared from brain; after 0.5, 1, and 7 h, only 30, 27, and 16% of the administered radioactivity, respectively, remained in the brain after intracerebral injection.
They also showed that brain levels of phosphodimethylaminoethanol increased to a maximum at 1-2 h and decreased afterwards, whereas concentrations of phosphatidylethanolamine increased continuously throughout the 7 h observation period.
This study further found that after i.p. injections of labeled dimethylaminoethanol, the brain content of phosphatidylethanolamine increased through the 7 h period and the levels were 10-40 fold higher than those of phosphodimethylaminoethanol.
Purification Methods
Dry the amine with anhydrous K2CO3 or KOH, and fractionally distil it. [Beilstein 4 IV 1424.]
2-Dimethylaminoethanol Preparation Products And Raw materials
Raw materials
ETHYLENE OXIDE 2-Chloroethanol Dimethylamine
Preparation Products
5-FLUORO-2-PICOLINIC ACID PROPIONYLTHIOCHOLINE IODIDE 1-[6-(Trifluoromethyl)pyridin-2-yl]piperazine polyurethane adhesive 691 ACETYLTHIOCHOLINE IODIDE 2-Dimethylaminoethyl chloride hydrochloride 4-(2-(DIMETHYLAMINO)ETHOXY)-3,5-DICHLOROBENZENAMINE 2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE 2-Chloro-6-trifluoromethylnicotinic acid N,N-Dimethylethylenediamine DOWEX(R) 1X8 S-BUTYRYLTHIOCHOLINE IODIDE 1-(2-DIMETHYLAMINOETHYL)PIPERAZINE 2-Trifluoromethyl-6-pyridinecarboxylic acid N,N-Dimethyltryptamine Meclofenoxate hydrochloride 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate 2-bromoethyldimethylamine 2-Chloro-3,6-dimethylpyridine
OTHER PRODUCTS OF ATAMAN KIMYA THAT MIGHT BE OF INTEREST:
DMIPA
DMAE
DEAE
MOPA
Cyclohexylamine
Ethylenediamine
Morpholine
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