From Wikipedia, the free encyclopedia
Dimethylethanolamine
Names
Preferred IUPAC name
2-(Dimethylamino)ethan-1-ol
Other names
Deanol Dimethyl ethanolamine Dimethylaminoethanol N ,N -DimethylaminoethanolN ,N -Dimethylethanolamine
Identifiers
Abbreviations
DMAE, DMEA
1209235
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.003.221
EC Number
KEGG
MeSH
Deanol
RTECS number
UNII
UN number
2051
InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
N Key: UEEJHVSXFDXPFK-UHFFFAOYSA-N
N
Properties
C 4 H 11 N O
Molar mass
89.138 g·mol−1
Appearance
Colourless liquid
Odor
Fishy, ammoniacal
Density
890 mg mL−1
Melting point
−59.00 °C; −74.20 °F; 214.15 K
Boiling point
134.1 °C; 273.3 °F; 407.2 K
log P
−0.25
Vapor pressure
816 Pa (at 20 °C)
Acidity (pK a )
9.23 (at 20 °C)
[1]
Basicity (pK b )
4.77 (at 20 °C)
1.4294
Pharmacology
N06BX04 (
WHO )
Hazards
GHS labelling :
Danger
H226 ,
H302 ,
H312 ,
H314 ,
H332
P280 ,
P305+P351+P338 ,
P310
Flash point
39 °C (102 °F; 312 K)
Explosive limits
1.4–12.2%
Lethal dose or concentration (LD, LC):
1.214 g/kg (dermal, rabbit) 2 g/kg (oral, rat)
Related compounds
Related alkanols
Related compounds
Diethylhydroxylamine
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Dimethylethanolamine (DMAE or DMEA) is an
organic compound with the formula (CH3 )2 NCH2 CH2 OH . 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 .
[2]
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 2-dimethylaminoethyl chloride.
[3] The
acrylate ester,
dimethylaminoethyl acrylate is used as a flocculating agent.
[4]
Related compounds are used in gas purification, e.g. removal of
hydrogen sulfide from sour gas streams.
Human uses
The
bitartrate salt of DMAE, i.e.
N ,N -dimethylethanolamine bitartrate , is sold as a dietary supplement.
[5] It is a white powder providing 37% DMAE.
[6]
Animal tests show possible benefit for improving
spatial memory
[7] and
working memory .
[8]
See also
References
^ Littel, RJ; Bos, M; Knoop, GJ (1990).
"Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K" (PDF) . Journal of Chemical and Engineering Data . 35 (3): 276–77.
doi :
10.1021/je00061a014 .
INIST
19352048 .
^ Matthias Frauenkron; Johann-Peter Melder; Günther Ruider; Roland Rossbacher; Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH.
doi :
10.1002/14356007.a10_001 .
ISBN
978-3-527-30673-2 .
^ Ashford, Robert D. (2011).
Ashford's Dictionary of Industrial Chemicals, 3rd edition . Wavelength. p. 3294.
ISBN
9780952267430 .
OCLC
863579691 . Retrieved 2023-10-04 .
^
"Dimethylaminoethyl Acrylate - Global Review 2020 to 2030" . Fact.MR . Retrieved 2023-10-04 .
^ Haneke, Karen E.; Masten, Scott (November 2002).
Dimethylethanolamine (DMAE) [108-01-0] and Selected Salts and Esters: Review of Toxicological Literature (Update) | Report on National Institute of Environmental Health Sciences Contract No. N01-ES-65402 (PDF) . National Toxicology Program (Report).
Archived (PDF) from the original on 2023-10-04. Retrieved 2015-04-30 – via Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina, 27709.
^
"Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate" .
Archived from the original on 2023-10-04.
^ Blin, Olivier; Audebert, Christine; Pitel, Séverine; Kaladjian, Arthur; Casse-Perrot, Catherine; Zaim, Mohammed; Micallef, Joelle; Tisne-Versailles, Jacky; Sokoloff, Pierre; Chopin, Philippe; Marien, Marc (2009-12-01).
"Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies" . Psychopharmacology . 207 (2): 201–212.
doi :
10.1007/s00213-009-1648-7 .
ISSN
1432-2072 .
PMID
19756528 .
S2CID
8535134 .
^ Levin, Edward D; Rose, Jed E; Abood, Leo (June 1995).
"Effects of nicotinic dimethylaminoethyl esters on working memory performance of rats in the radial-arm maze" . Pharmacology Biochemistry and Behavior . 51 (2–3): 369–373.
doi :
10.1016/0091-3057(94)00406-9 .
PMID
7667355 .
S2CID
20685322 .