Dimethylethanolamine

Dimethylethanolamine

Dimethylethanolamine
Skeletal formula of dimethylethanolamine
Ball-and-stick model of the dimethylethanolamine molecule
Names
IUPAC name
2-(Dimethylamino)ethanol
Other names
  • Deanol
  • Dimethylamino ethanol
Identifiers
 Y
Abbreviations DMAE, DMEA
ATC code N06
1209235
ChEBI  N
ChEMBL  N
ChemSpider  N
EC number 203-542-8
Jmol-3D images Image
KEGG  N
MeSH
PubChem
RTECS number KK6125000
UNII  Y
UN number 2051
Properties
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)
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
H226, H302, H312, H314, H332
P280, P305+351+338, P310
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%
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
  • 1.214 g kg−1 (dermal, rabbit)
  • 2 g kg−1 (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).
 N  (: Y/N?)

Dimethylaminoethanol and dimethylethanolamine (DMAE and DMEA respectively), with deanol, are common names for 2-(dimethylamino)ethanol.


Contents

  • Chemical structure and properties 1
  • Uses 2
    • Biochemical roles 2.1
    • Industrial uses 2.2
    • Nutraceutical uses 2.3
  • Further reading (secondary sources) 3
  • Further reading (primary sources) 4
  • See also 5
  • References 6

Chemical structure and properties

This compound has tertiary amine and primary alcohol groups as functional groups.. The alcohol functionality, in combination with the amine and its low molecular weight imparts water solubility on the compound, and makes ester derivatives possible; the amine functionality gives the compound its alkaline character, and allows for formulation of salts of the compound.

Uses

Characteristics arising from its chemical features as well as from its overall structural similarity to chemical compounds involved in primary metabolism and neurophysiology

Biochemical roles

Dimethylaminoethanol is a structural relative of choline, and a biochemical precursor to the neurotransmitter acetylcholine.[2][3] Dimethylaminoethanol serves as a precursor of choline in the liver. In the brain, DMAE is incorporated into phospholipids, as phosphatidyldimethylethanolamine (PDME), which can then be converted, via N-methylation, to phosphatidylcholine. As a component of nerve membranes, PDME may increase fluidity and permeability, and acting as an antioxidant.

Industrial uses

Industrial uses include as a bulk chemical in cholinergic functions.

DMEA is used in bulk quantities for water treatment, in the coatings industry, and as a curing agent for polyurethanes and epoxy resins. It is also used in the chemical synthesis of dyestuffs, pharmaceuticals, emulsifiers, textile auxiliaries, as an additive to paint removers and amino resins, and as an additive to boiler water to provide corrosion resistance. For instance, 2-dimethylaminoethyl chloride hydrochloride is synthesized from dimethylaminoethanol, and serves as an intermediate that is widely used for the manufacture of pharmaceuticals.[4]

DMEA forms a number of salts with melting points below room temperature ionic liquids, (e.g. N,N-dimethylethanolammonium acetate and N,N-dimethylethanolammonium octanoate), which can be used in applications where alternatives to conventional solvents are required. [5]

Nutraceutical uses

The bitartrate salt of DMAE, i.e. 2-dimethylaminoethanol (+)-bitartrate, is sold as a dietary supplement.[6] It is a white powder providing 37% DMAE.[7]

Further reading (secondary sources)

  • Grossman, R (2005). "The role of dimethylaminoethanol in cosmetic dermatology". American journal of clinical dermatology 6 (1): 39–47.  
  • 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): 215–29.  

Further reading (primary sources)

  • As a putative treatment for  
  • As a putative stimulant of alertness and  
  • As a putative treatment for tremor, and possible cause of  
  • As a putative treatment for  
  • As a putative agent effecting animal life-span: Cherkin A, Exkardt MJ (January 1977). "Effects of dimethylaminoethanol upon life-span and behavior of aged Japanese quail". J Gerontol 32 (1): 38–45.  
  • Questioning biosynthetic relationship with acetylcholine: Zahniser, N. R.; Chou, D; Hanin, I (1977). "Is 2-dimethylaminoethanol (deanol) indeed a precursor of brain acetylcholine? A gas chromatographic evaluation". The Journal of pharmacology and experimental therapeutics 200 (3): 545–59.  

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.  
  2. ^ Grossman, R (2005). "The role of dimethylaminoethanol in cosmetic dermatology". American journal of clinical dermatology 6 (1): 39–47.  
  3. ^ Pfeiffer, C. C.; Jenney, E. H.; Gallagher, W; Smith, R. P.; Bevan Jr, W; Killam, K. F.; Killam, E. K.; Blackmore, W (1957). "Stimulant effect of 2-dimethylaminoethanol; possible precursor of brain acetylcholine". Science (New York, N.Y.) 126 (3274): 610–1.  
  4. ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN 978-0-9522674-3-0, p. 3294.
  5. ^ Sanders, M. W.; Wright, L; Tate, L; Fairless, G; Crowhurst, L; Bruce, N. C.; Walker, A. J.; Hembury, G. A.; Shimizu, S (2009). "Unexpected preferential dehydration of artemisinin in ionic liquids". The Journal of Physical Chemistry A 113 (38): 10143–5.  
  6. ^ Karen E. Haneke & Scott Masten, 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, November 2002, from Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina 27709, see [4], accessed 30 April 2015.
  7. ^ Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate