Dimethylethanolamine

Dimethylethanolamine
Identifiers
Abbreviations DMAE
CAS number 108-01-0 YesY
ChemSpider 13835861 YesY
UNII 2N6K9DRA24 YesY
EC number 7902
ChEMBL CHEMBL122588 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4H11NO
Molar mass 89.14 g mol−1
Density 0.89 g/mL
Melting point

-70 °C, 203 K, -94 °F

Boiling point

133–134 °C

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 clear, pale-yellow liquid.

Contents

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.[1]

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

Biochemical precursor

Dimethylaminoethanol is related to choline and may be a biochemical precursor to the neurotransmitter acetylcholine, although this conclusion has been disputed.[3] It is believed that dimethylaminoethanol is methylated to produce choline in the brain.[3] 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.[3]

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.[4] Research for attention deficit hyperactivity disorder (ADHD) has been promising, though inconclusive.[5] 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.[6]

See also

References

  1. ^ 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. http://pubs.acs.org/doi/abs/10.1021/jp906436e. 
  2. ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN: 978-0-9522674-3-0, page 3294
  3. ^ a b c 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. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=850128. 
  4. ^ 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. 
  5. ^ Knobel M (1974). "Approach to a combined pharmacologic therapy of childhood hyperkinesis". Behav Neuropsychiatry 6 (1–12): 87–90. PMID 4619768. 
  6. ^ Cherkin A, Exkardt MJ (January 1977). "Effects of dimethylaminoethanol upon life-span and behavior of aged Japanese quail". J Gerontol 32 (1): 38–45. PMID 830732. http://geronj.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=830732. 

Studies

  • As a treatment for tardive dyskinesia
    Haug BA, Holzgraefe M (1991). "Orofacial and respiratory tardive dyskinesia: potential side effects of 2-dimethylaminoethanol (deanol)?". Eur. Neurol. 31 (6): 423–5. doi:10.1159/000116708. PMID 1756771.