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
Skeletal formula of dimethylethanolamine
Ball-and-stick model of the dimethylethanolamine molecule
Names
Preferred IUPAC name
2-(Dimethylamino)ethan-1-ol
Other names
  • Deanol
  • Dimethyl ethanolamine
  • Dimethylaminoethanol
  • N,N-Dimethylaminoethanol
  • N,N-Dimethylethanolamine
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:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
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).
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Infobox references

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.

Nutraceutical 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
  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 978-3-527-30673-2.
  3. "Ashford's Dictionary of Industrial Chemicals, 3rd edition". WorldCat.org. 2011. p. 3294. ISBN 9780952267430. OCLC 863579691. Retrieved 2023-10-04.
  4. "Dimethylaminoethyl Acrylate - Global Review 2020 to 2030". Fact.MR. Retrieved 2023-10-04.
  5. 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.
  6. "Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate". Archived from the original on 2023-10-04.
  7. 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.
  8. 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.
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