View source for Dimethylethanolamine

{{chembox new|
 ImageFile=DMAE.png|
 IUPACName=2-(dimethylamino)ethanol| 
 OtherNames=dimethylamino ethanol<br>Deanol| 
 Abbreviations=DMAE|
 Formula=[[Carbon|C]]<sub>4</sub>[[Hydrogen|H]]<sub>11</sub>[[Nitrogen|N]][[Oxygen|O]]|
 MolarMass=89.14|
 CASNo=108-01-0|
 Density=0.89 g/mL|
 Solubility=|
 MeltingPt=-70|
 BoilingPt=133-134|
 pKa=|
 pKb=|
 IsoelectricPt=|
 DeltaHf=|
 DeltaHc=|
 EINECS=|
 PubChem=|
 SMILES=CN(C)CCO|
 InChI=|
}}


==Overview==
'''Dimethylaminoethanol''', also known as '''DMAE''' or '''dimethylethanolamine''', is an [[organic compound]]. This compound also goes by the names of N,N-dimethyl-2-aminoethanol, beta-dimethylaminoethyl alcohol, beta-hydroxyethyldimethylamine and Deanol. It is a liquid with a color that ranges from clear to pale yellow.

== Industrial Uses ==

Dimethylaminoethanol is used as a [[curing agent]] for [[polyurethane]]s and [[epoxy resins]]. It is used to the synthesis of [[dye|dyestuff]]s, textile auxiliaries, [[pharmaceutical]]s, [[emulsifier]]s, and [[corrosion inhibitor]]s. Also it is an [[additive]] to [[paint]] removers, [[boiler]] water, and [[amino]] [[resin]]s.

== Biochemical Precursor ==

Dimethylaminoethanol is related to [[choline]] and is a biochemical precursor to the neurotransmitter [[acetylcholine]], and found naturally in fishes like sardines and anchovies. It is reported to have [[nootropic]] effects, although research on this chemical has found both positive and negative potential results.

It is believed that dimethylaminoethanol is [[methyl]]ated to produce choline in the brain<ref>N. R. Zahniser, D. Chou, I. Hanin. "[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=850128 Is 2-dimethylaminoethanol (deanol) indeed a precursor of brain acetylcholine? A gas chromatographic evaluation]", ''Journal of Pharmacology and Experimental Therapeutics'' '''200'''(3):545–559, 1977.</ref>. It is known that dimethylaminoethanol is processed by the [[liver]] into choline; however, the choline molecule is charged and cannot pass the [[blood-brain barrier]].

=== Research ===

Short term studies have shown an increase in vigilance and alertness, with a positive influence on [[mood]]<ref>W. Dimpfel, W. Wedekind, I. Keplinger, "[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=12844472 Efficacy of dimethylaminoethanol (DMAE) containing vitamin-mineral drug combination on EEG patterns in the presence of different emotional states]", ''European Journal Medical Research'' '''8'''(5):183-191,  2003.</ref>.  Long term studies are equivocal.  Some showed dimethylaminoethanol to increase the lifespan of animals in which it was tested, while others indicate a possible reduction in the [[average life span]] of [[quail]]<ref>A. Cherkin, M.J. Exkardt, "[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=830732 Effects of dimethylaminoethanol upon life-span and behavior of aged Japanese quail]", ''Journal of Gerontology'' '''32'''(1):38-45, 1977.</ref>. With the uncertainty of whether this could be extrapolated to [[human]]s, dimethylaminoethanol supplementation is not generally recommended.  It is possible that dose is a major determining factor in the overall effects of dimethylaminoethanol - a high dose could produce the opposite effects than sought and contribute to life-shortening.<ref>G. Morissette, L. Germain, F. Marceau, "[http://www.blackwell-synergy.com/doi/abs/10.1111/j.1365-2133.2007.07681.x The antiwrinkle effect of topical concentrated 2-dimethylaminoethanol involves a vacuolar cytopathology]", ''British Journal of Dermatology'' '''156'''(3) pp.433-439, 2007.</ref>

A recent study indicates that synthetic DMAE applied topically may alter the appearance of skin cells. "From our point of view the cells are altered. They stop dividing, they stop secreting, and after 24 hours a certain proportion of them die," said Dr. Francois Marceau of the Centre Hospitalier Universitaire de Quebec.

Marceau, a cell biologist, said he is reluctant to recommend that these products not be used. However, the findings make it clear that more research is needed on how these and similar products work. "I don't want to scare people," he added. "The risk is probably not very big, but in my opinion it hasn't been measured accurately." <ref>Anne Harding, "[http://www.reuters.com/article/healthNews/idUSCOL85568520070418 "Instant face lift" chemical DMAE damages skin cells]",  ''Reuters Health'' Wed Apr 18, 2007 7:50PM EDT</ref><ref>Jean-François Huppé, "[http://www.eurekalert.org/pub_releases/2007-04/ul-acc041107.php Anti-wrinkle compound causes pathological reaction in skin cells]", ''Eureka Alert!'', 11-Apr-2007 </ref>.

==See also==
*[[Ethanolamine]]
*[[Methylethanolamine]]

==References==
<references/>

==Other studies==
*Earliest research
*:Pfeiffer C, et al. ''Stimulant effect of 2-dimethylaminoethanol; possible precursor of brain acetylcholine.'' [[Science (journal)|Science]] 126(3274):610-611, 1957. [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=13467254]

*As a treatment for [[tardive dyskinesia]]
*:Haug BA, Holzgraefe M. "Orofacial and respiratory tardive dyskinesia: potential side effects of 2-dimethylaminoethanol (deanol)?" ''European Neurology'' 31(6):423–425, 1991. [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=1756771]

*As an unsuccessful treatment for [[Alzheimer's disease]]
*:Fisman M, Mersky H, Helmes E. "Double-blind trial of 2-dimethylaminoethanol in Alzheimer's disease." ''American Journal of Psychiatry'' 138(7):970–972, 1981. [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=7020434]
{{Psychostimulants, agents used for ADHD and nootropics}}
[[Category:Amines]]
[[Category:Alcohols]]
[[Category:Nootropics]]

[[de:Dimethylaminoethanol]]
[[fr:Diméthylaminoéthanol]]
[[ja:ジメチルアミノエタノール]]
[[pl:Deanol]]
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