Dimethylethanolamine

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Dimethylethanolamine
Skeletal formula of dimethylethanolamine
Identifiers
Abbreviations DMAE, DMEA
CAS number 108-01-0 YesY
PubChem 7902
ChemSpider 13854944 N
UNII 2N6K9DRA24 YesY
EC number 203-542-8
UN number 2051
KEGG D07777 N
MeSH Deanol
ChEBI CHEBI:271436 N
ChEMBL CHEMBL1135 N
RTECS number KK6125000
ATC code N06BX04
Beilstein Reference 1209235
Jmol-3D images Image 1
Properties
Molecular formula C4H11NO
Molar mass 89.14 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)
Refractive index (nD) 1.4294
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H226, H302, H312, H314, H332
GHS precautionary statements P280, P305+351+338, P310
EU Index 603-047-00-0
EU classification Corrosive C
R-phrases R10, R20/21/22, R34
S-phrases (S1/2), S25, S26, S36/37/39, S45
Flash point 39 °C (102 °F; 312 K)
Explosive limits 1.4–12.2%
LD50
  • 1.214 g kg−1 (dermal, rabbit)
  • 2 g kg−1 (oral, rat)
Related compounds
Related alkanols
Related compounds Diethylhydroxylamine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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[edit]

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[edit]

Industrial uses[edit]

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[edit]

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]

The bitartrate salt of DMAE, i.e. 2-dimethylaminoethanol (+)-bitartrate, is sold as a dietary supplement.[9] It is a white powder providing 37% DMAE.[10]

See also[edit]

References[edit]

  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. ^ 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. 
  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. ^ "Dimethylethanolamine (DMAE) [108-01-0] and Selected Salts and Esters". National Institute of Environmental Health Sciences. November 2002. Retrieved 10/08/2014.  Check date values in: |accessdate= (help)
  10. ^ Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate

Studies[edit]

  • 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.