Dimethylethanolamine

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.[2]

Dimethylethanolamine
Names
Preferred IUPAC name
2-(Dimethylamino)ethan-1-ol
Other names
deanol, dimethylaminoethanol, dimethylaminoethanol
Identifiers
3D model (JSmol)
Abbreviations DMAE, DMEA
1209235
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.221
EC Number
  • 203-542-8
KEGG
MeSH Deanol
RTECS number
  • KK6125000
UNII
UN number 2051
  • InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3 N
    Key: UEEJHVSXFDXPFK-UHFFFAOYSA-N N
  • CN(C)CCO
Properties
C4H11NO
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 (pKa) 9.23 (at 20 °C)[1]
Basicity (pKb) 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−1 (dermal, rabbit)
  • 2 g kg−1 (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).
N verify (what is YN ?)
Infobox references

Industrial uses

It is a precursor to other chemicals, such as the nitrogen mustard 2-dimethylaminoethyl chloride.[3] The acrylate 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 salt of DMAE, i.e. 2-dimethylaminoethanol (+)-bitartrate, is sold as a dietary supplement.[4] It is a white powder providing 37% DMAE.[5]

Animal tests show possible benefit for improving spatial memory[6] and working memory.[7]

See also

References
  1. 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.
  2. 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 978-3527306732.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  3. Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN 978-0-9522674-3-0, p. 3294.
  4. Karen E. Haneke & Scott Masten, 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, November 2002, from Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina 27709, see , accessed 30 April 2015.
  5. Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate
  6. Blin, O., Audebert, C., Pitel, S. et al. Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies. Psychopharmacology 207, 201 (2009). https://doi.org/10.1007/s00213-009-1648-7
  7. 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.
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