Dimethylethanolamine (DMAE or DMEA) is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (CH
3)
2NCH
2CH
2OH. It is
bifunctional
In organic chemistry, when a single organic molecule has two different functional groups, it is called a bifunctional molecule . A bifunctional molecule has the properties of two different types of functional groups, such as an alcohol (), amide ( ...
, containing both a
tertiary amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such a ...
and
primary alcohol
A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group.
In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
s. It is a colorless viscous liquid. It is used in skin care products for improving skin tone and
also taken orally as a
nootropic
Nootropics ( , or ) (colloquial: smart drugs and cognitive enhancers, similar to adaptogens) are a wide range of natural or synthetic supplements or drugs and other substances that are claimed to improve cognitive function or to promote re ...
. It is prepared by the
ethoxylation
Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.
In the usual application, alcohols and phenols are converted i ...
of
dimethylamine
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to aroun ...
.
Industrial uses
Dimethylaminoethanol is used as a curing agent for polyurethanes and epoxy resins. It is a precursor to other chemicals, such as the
nitrogen mustard
Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen m ...
2-dimethylaminoethyl chloride. The
acrylate
Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion C H2=CHC OO−. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acry ...
ester is used as a flocculating agent.
Related compounds are used in gas purification, e.g. removal of hydrogen sulfide from sour gas streams.
Nutraceutical uses
The
bitartrate
, Section2 = {{Chembox Properties
, C=4 , H=5 , O=6
, Formula_Charge = −
, ConjugateAcid = Tartaric acid
, ConjugateBase = Tartrate
Bitartrate is an anion which is the conjugate base of tartaric acid. It may also refer to any salt or ...
salt of DMAE, i.e. 2-dimethylaminoethanol (+)-bitartrate, is sold as a dietary supplement. It is a white powder providing 37% DMAE.
Animal tests show possible benefit for improving
spatial memory
In cognitive psychology and neuroscience, spatial memory is a form of memory responsible for the recording and recovery of information needed to plan a course to a location and to recall the location of an object or the occurrence of an event. Sp ...
and
working memory
Working memory is a cognitive system with a limited capacity that can hold information temporarily. It is important for reasoning and the guidance of decision-making and behavior. Working memory is often used synonymously with short-term memory, ...
.
[Edward D Levin, Jed E Rose, Leo Abood. Effects of nicotinic dimethylaminoethyl esters on working memory performance of rats in the radial-arm maze. Pharmacology Biochemistry and Behavior. Volume 51, Issues 2–3, 1995, Pages 369-373, ISSN 0091-3057, https://doi.org/10.1016/0091-3057(94)00406-9.]
See also
*
Choline Choline is an essential nutrient for humans and many other animals. Choline occurs as a cation that forms various salts (X− in the depicted formula is an undefined counteranion). Humans are capable of some ''de novo synthesis'' of choline but re ...
*
Diphenhydramine
Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremor in parkinsonism, and nausea. It is taken by mouth, injected into a vein ...
*
Doxylamine
Doxylamine, sold under the brand name Unisom among others, is an antihistamine medication which is used in the treatment of insomnia and allergies. In combination with pyridoxine ( vitamin B6), it is also used to treat morning sickness in pregna ...
*
Ethanolamine
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an 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 wit ...
*
Meclofenoxate
Meclofenoxate (International Nonproprietary Name, INN, British Approved Name, BAN; brand name Lucidril, also known as centrophenoxine) is a cholinergic nootropic used as a dietary supplement. It is an ester of dimethylethanolamine (DMAE) and 4-Ch ...
(Centrophenoxine)
*
Orphenadrine
Orphenadrine (sold under many brand names) is an anticholinergic drug of the ethanolamine antihistamine class; it is closely related to diphenhydramine. It is a muscle relaxant that is used to treat muscle pain and to help with motor control in Pa ...
References
{{Acetylcholine receptor modulators
Dimethylamino compounds
Primary alcohols
Cholinergics
Nootropics
Corrosion inhibitors
Ethanolamines