Dimethylethanolamine

Dimethylethanolamine
IUPAC name 2-(Dimethylamino)ethanol
Other names Dimethylamino ethanol Deanol
Identifiers
Abbreviations	DMAE
CAS number	108-01-0 Y
ChemSpider	13835861 Y
UNII	2N6K9DRA24 Y
EC number	7902
ChEMBL	CHEMBL122588 Y
Jmol-3D images	Image 1
SMILES CC(C)(N)CO
InChI InChI=1S/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3 Y Key: CBTVGIZVANVGBH-UHFFFAOYSA-N Y InChI=1/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3 Key: CBTVGIZVANVGBH-UHFFFAOYAK
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
Y (verify) (what is: Y/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.

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

• Ethanolamine
• Methylethanolamine
• Choline

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

• Earliest research

  Pfeiffer CC, Jenney EH, Gallagher W, et al. (September 1957). "Stimulant effect of 2-dimethylaminoethanol; possible precursor of brain acetylcholine". Science 126 (3274): 610–1. doi:10.1126/science.126.3274.610. PMID 13467254. http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=13467254. 

• 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. 

• As an unsuccessful treatment for Alzheimer's disease

  Fisman M, Mersky H, Helmes E (July 1981). "Double-blind trial of 2-dimethylaminoethanol in Alzheimer's disease". Am J Psychiatry 138 (7): 970–2. PMID 7020434. http://ajp.psychiatryonline.org/cgi/pmidlookup?view=long&pmid=7020434.