Dimethylethanolamine

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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
Abbreviations DMAE, DMEA
ATC code N06BX04
1209235
108-01-0 YesY
ChEBI CHEBI:271436 N
ChEMBL ChEMBL1135 N
ChemSpider 13854944 N
EC number 203-542-8
Jmol-3D images Image
KEGG D07777 N
MeSH Deanol
PubChem 7902
RTECS number KK6125000
UNII 2N6K9DRA24 YesY
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
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%
  • 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 is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Dimethylaminoethanol and dimethylethanolamine (DMAE and DMEA respectively), with deanol, are common names for the bifunctional organic compound 2-(dimethylamino)ethanol that has tertiary amine and primary alcohol groups as functional groups,[2] with characteristics arising from these chemical features as well as from its overall structural similarity to chemical compounds involved in primary metabolism (e.g., choline, the further N-methylated derivative of DMAE) and neurophysiology (e.g., acetylcholine, the O-acetyl derivative of choline). 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.[not verified in body] Biochemical roles are based on the ability of biological systems to convert DMAE to into choline (and the local and systemic impacts of this), and on its ability to serve directly as a choline analog (e.g., during phospholipid biosynthesis).[not verified in body] Industrial uses include as a bulk chemical in water purification, as a fine chemical precursor in pharmaceutical and other organic syntheses, and as an additive in a variety of applications, including with resins and coatings.[not verified in body] There is expanding interest in use of DMAE as a nutraceutical, and it is has been tested as a possible therapeutic agent related to a variety of cholinergic functions.[not verified in body]

The substance is available in various forms, depending on chemical purity and the nature of the salt form, if any.[not verified in body]

Chemical structure and properties[edit]

The alcohol functionality of DMAE, 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.[citation needed] The substance is available in various forms, depending on chemical purity and the nature of the salt form, if any.[citation needed]

Uses[edit]

Biochemical roles[edit]

Dimethylaminoethanol is a structural relative of choline, and a biochemical precursor to the neurotransmitter acetylcholine.[3][4] Dimethylaminoethanol serves as a precursor of choline in the liver.[citation needed] In the brain, DMAE is incorporated into phospholipids, as phosphatidyldimethylethanolamine (PDME), which can then be converted, via N-methylation, to phosphatidylcholine.[citation needed] As a component of nerve membranes, PDME may increase fluidity and permeability, and acting as an antioxidant.[citation needed]

Industrial uses[edit]

DMEA is used in bulk quantities for water treatment, in the coatings industry, and as a curing agent for polyurethanes and epoxy resins.[citation needed] It is also used in the chemical synthesis of dyestuffs, pharmaceuticals, emulsifiers, textile auxiliaries,[citation needed] as an additive to paint removers and amino resins,[citation needed] and as an additive to boiler water to provide corrosion resistance.[citation needed] For instance, 2-dimethylaminoethyl chloride hydrochloride is synthesized from dimethylaminoethanol, and serves as an intermediate that is widely used for the manufacture of pharmaceuticals.[5][full citation needed]

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

Nutraceutical uses[edit]

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)[edit]

  • Grossman, R (2005). "The role of dimethylaminoethanol in cosmetic dermatology". American journal of clinical dermatology 6 (1): 39–47. PMID 15675889.  edit
  • 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. PMID 2517957.  edit

Further reading (primary sources)[edit]

  • On its use as an ionic liquid: 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. doi:10.1021/jp906436e. PMID 19722599.  edit
  • As a putative treatment for ADHD: Knobel M (1974). "Approach to a combined pharmacologic therapy of childhood hyperkinesis". Behav Neuropsychiatry 6 (1–12): 87–90. PMID 4619768. 
  • As a putative stimulant of alertness and mood: 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. 
  • As a putative 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 a putative 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. doi:10.1176/ajp.138.7.970. PMID 7020434. 
  • 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. doi:10.1093/geronj/32.1.38. PMID 830732. 
  • 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. PMID 850128.  edit

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. ^ Other names include N,N-dimethyl-2-aminoethanol, β-dimethylaminoethyl alcohol, and β-hydroxyethyldimethylamine.[citation needed]
  3. ^ Grossman, R (2005). "The role of dimethylaminoethanol in cosmetic dermatology". American journal of clinical dermatology 6 (1): 39–47. PMID 15675889.  edit
  4. ^ 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. PMID 13467254.  edit
  5. ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN 978-0-9522674-3-0, p. 3294.[full citation needed]
  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 [2], accessed 30 April 2015.
  7. ^ Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate