Deanol

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Template:Chembox ECNumberTemplate:Chembox E numberTemplate:Chembox UNNumberTemplate:Chembox GHSPictogramsTemplate:Chembox GHSSignalWordTemplate:Chembox HPhrasesTemplate:Chembox PPhrasesTemplate:Chembox Lethal amounts (set)
Deanol
Skeletal formula of dimethylethanolamine
Ball-and-stick model of the dimethylethanolamine molecule
Names
IUPAC name
2-(Dimethylamino)ethanol
Other names
  • Deanol
  • Dimethylamino ethanol
Identifiers
3D model (JSmol)
Abbreviations DMAE, DMEA
Beilstein Reference 1209235
ChEBI
ChEMBL
ChemSpider
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KEGG
MeSH Deanol
RTECS number KK6125000
UNII
Properties
C4H11NO
Molar mass 89.14 g·mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 890 mg mL−1
Melting point
Boiling point
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)
Refractive index (nD) 1.4294
Hazards
Flash point {{{value}}}
Explosive limits 1.4–12.2%
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Dimethylaminoethanol, also known as dimethylethanolamine (DMAE and DMEA respectively), is a primary alcohol. This compound also goes by the names of N,N-dimethyl-2-aminoethanol, beta-dimethylaminoethyl alcohol, beta-hydroxyethyldimethylamine and Deanol. It is a transparent, pale-yellow liquid.

Biochemical significance

Dimethylaminoethanol is related to choline and may be a biochemical precursor to the neurotransmitter acetylcholine, although this conclusion has been disputed based on a 1977 rat experiment.[2] It is commonly believed that dimethylaminoethanol is methylated to produce choline in the brain, but this has been shown not to be the case (in a rat experiment).[2] It is known that dimethylaminoethanol is processed by the liver into choline; however, in a rat experiment the choline molecule is charged and cannot pass the blood–brain barrier.[2] In the brain, DMAE is instead bound to phospholipids in place of choline to produce phosphatidyl-dimethylaminoethanol. This is then incorporated into nerve membranes, increasing fluidity and permeability, and acting as an antioxidant.[3]

Uses

Industrial uses

Dimethylaminoethanol is used as a curing agent for polyurethanes and epoxy resins. It is also used in mass quantities for water treatment, and to some extent in the coatings industry. It is used in the synthesis of dyestuffs, textile auxiliaries, pharmaceuticals, emulsifiers, and corrosion inhibitors. It is also an additive to paint removers, boiler water and amino resins. It forms a number of salts with melting points below room temperature (ionic liquids) such as N,N-dimethylethanolammonium acetate and N,N-dimethylethanolammonium octanoate, which have been used as alternatives to conventional solvents.[4]

2-Dimethylaminoethyl chloride hydrochloride is an intermediate made from dimethylaminoethanol that is widely used for the manufacture of pharmaceuticals.[5]

Biomedical research

Short-term studies have shown an increase in vigilance and alertness with a positive influence on mood following administration of DMAE, vitamins, and minerals in individuals suffering from borderline emotional disturbance.[6] Research for ADHD has been promising, though inconclusive.[7] A study showed dimethylaminoethanol to decrease the average life span of aged quail.[8] Three other studies showed an increase in lifespan of mice [9]

The bitartrate salt of DMAE, i.e. 2-dimethylaminoethanol (+)-bitartrate, is sold as a dietary supplement.[10] It is a white powder providing 37% DMAE.[11]

See also

References

  1. Littel, RJ, Bos, M, Knoop, GJ (1990). "Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K". J. Chem. Eng. Data. 35: 276–277. doi:10.1021/je00061a014.
  2. 2.0 2.1 2.2 Zahniser NR, Chou D, Hanin I (March 1977). "Is 2-dimethylaminoethanol (deanol) indeed a precursor of brain acetylcholine? A gas chromatographic evaluation". J. Pharmacol. Exp. Ther. 200 (3): 545–59. PMID 850128.
  3. Zs-Nagy, I (1989). "On the role of intracellular physicochemistry in quantitative gene expression during aging and the effect of centrophenoxine. A review". Archives of gerontology and geriatrics. 9 (3): 215–229.
  4. Sanders MW, Wright L, Tate L, Fairless G, Crowhurst L, Bruce NC, Walker AJ, Hembury GA, Shimizu S (September 2009). "Unexpected preferential dehydration of artemisinin in ionic liquids". J. Phys. Chem. A. 113 (38): 10143–45. doi:10.1021/jp906436e. PMID 19722599.
  5. Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN 978-0-9522674-3-0, page 3294
  6. Dimpfel W, Wedekind W, Keplinger I (May 2003). "Efficacy of dimethylaminoethanol (DMAE) containing vitamin-mineral drug combination on EEG patterns in the presence of different emotional states". Eur. J. Med. Res. 8 (5): 183–91. PMID 12844472.
  7. Knobel M (1974). "Approach to a combined pharmacologic therapy of childhood hyperkinesis". Behav Neuropsychiatry. 6 (1–12): 87–90. PMID 4619768.
  8. Cherkin A, Exkardt MJ (January 1977). "Effects of dimethylaminoethanol upon life-span and behavior of aged Japanese quail". J Gerontol. 32 (1): 38–45. doi:10.1093/geronj/32.1.38. PMID 830732.
  9. Cherkin A, Exkardt MJ (January 1977). "Effects of dimethylaminoethanol upon life-span and behavior of aged Japanese quail". J Gerontol. 32 (1): 38–45. doi:10.1093/geronj/32.1.38. PMID 830732.
  10. "Dimethylethanolamine (DMAE) [108-01-0] and Selected Salts and Esters" (PDF). National Institute of Environmental Health Sciences. November 2002. Retrieved 8 October 2014.
  11. Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate

Studies



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