Dimethylethanolamine
From Wikipedia, the free encyclopedia
| Dimethylethanolamine | |
|---|---|
 |
|
|
2-(Dimethylamino)ethanol |
|
|
Other names
|
|
| Identifiers | |
| Abbreviations | DMAE, DMEA |
| CAS number | 108-01-0  |
| PubChem | 7902 |
| ChemSpider | 13854944  |
| UNII | 2N6K9DRA24 |
| EC number | 203-542-8 |
| UN number | 2051 |
| KEGG | D07777 |
| MeSH | Deanol |
| ChEBI | CHEBI:271436 |
| ChEMBL | CHEMBL1135 |
| RTECS number | KK6125000 |
| ATC code | N06 |
| 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 °C, 214.15 K, -74 °F |
| Boiling point |
134 °C, 407.2 K, 273 °F |
| 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 |    |
| 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 |  C |
| R-phrases | R10, R20/21/22, R34 |
| S-phrases | (S1/2), S25, S26, S36/37/39, S45 |
| Flash point | 39 °C |
| Explosive limits | 1.4–12.2% |
| LD50 |
|
| Related compounds | |
| Related alkanols | |
| Related compounds | Diethylhydroxylamine |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| 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.
Contents |
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.[2]
2-Dimethylaminoethyl chloride hydrochloride is an intermediate made from dimethylaminoethanol that is widely used for the manufacture of pharmaceuticals.[3]
Biochemical precursor[edit]
Dimethylaminoethanol is related to choline and may be a biochemical precursor to the neurotransmitter acetylcholine, although this conclusion has been disputed.[4] It is commonly believed that dimethylaminoethanol is methylated to produce choline in the brain, but this has been shown not to be the case.[4] 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.[4] 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.[5]
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 attention deficit hyperactivity disorder (ADHD) has been promising, though inconclusive.[7] A study showed dimethylaminoethanol to decrease the average life span of aged quail.[8]
See also[edit]
References[edit]
- ^ 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.
- ^ 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.
- ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN 978-0-9522674-3-0, page 3294
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Knobel M (1974). "Approach to a combined pharmacologic therapy of childhood hyperkinesis". Behav Neuropsychiatry 6 (1–12): 87–90. PMID 4619768.
- ^ 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.
Studies[edit]
- 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.
- 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.
|
||||||||||||||||||||||||||||||||
|
||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
