N, N -dimethylethanolamine

Structural formula
General
Non-proprietary name	Dimethylaminoethanol
other names	2- (Dimethylamino) -ethan-1-ol ( IUPAC ); Dimethylethanolamine; Norcholine; DMAE; Deanol; DIMETHYL MEA ( INCI ) ;
Molecular formula	C 4 H 11 NO
Brief description	colorless liquid with an ammonia- like odor
External identifiers / databases
EC number	203-542-8
ECHA InfoCard	100.003.221
PubChem	7902
ChemSpider	13854944
DrugBank	DB13352
Wikidata	Q241049
Drug information
ATC code	N06 BX04
Drug class	Nootropics
properties
Molar mass	89.14 g mol −1
Physical state	liquid
density	0.89 g cm −3 (20 ° C)
Melting point	<−40 ° C
boiling point	131 ° C
Vapor pressure	39.9 hPa (50 ° C)
solubility	miscible with water and ethanol
Refractive index	1.4300 (20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 226-331-312-302-314-335
	P: 210-280-303 + 361 + 353-305 + 351 + 338-312-405
Toxicological data	2000 mg kg −1 ( LD 50 , rat , oral ) ; > 1220 mg kg −1 ( LD 50 , rabbit , transdermal , median value) ; > 5.98 mg l −1 ( LC 50 , rat , inhalation, 4 h , median value) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N, N -Dimethylethanolamine (according to IUPAC nomenclature : 2- (dimethylamino) ethan-1-ol , also known as DMEA for short ) is an organic-chemical compound from the group of alkylated amino alcohols . It isclosely related to the neurotransmitter acetylcholine via choline (the trimethylethanolammonium cation). The compound is an important intermediate product in the chemical and pharmaceutical industries , which has a wide range of applications.

Occurrence

Dimethylaminoethanol occurs as a metabolic product of the metabolism of choline in many living things. Larger amounts are found in fish ( sardines , salmon , anchovies ).

Extraction and presentation

N , N- dimethylethanolamine is produced industrially by reacting ethylene oxide with dimethylamine at temperatures of 125-160 ° C. and pressures of 15-30 bar in the presence of catalytic amounts of water in liquid-cooled jacketed tubular reactors .

The product is purified and worked up by multi-stage distillation in rectification columns .

Furthermore, can the dimethylaminoethanol, by methylation of monoethanolamine are synthesized.

properties

The flash point is 31 ° C, the ignition temperature 220 ° C.

use

Dimethylaminoethanol is used as an aid to dispersion of pigments in water-based paints use. It is also required as an intermediate or starting material for the production of dyes , emulsifiers , corrosion protection agents , textile auxiliaries, cosmetics and pharmaceuticals .

Dimethylaminoethanol is said to have a large number of positive effects, including nootropic effects , for which, however, there is no clear evidence. In Alzheimer -Patients no consistent results were observed. One author reported increased lucid dreams after using DMAE.

Dimethylaminoethanol as a topical gel is said to reduce the formation of wrinkles.

safety instructions

As a tertiary amine, dimethylaminoethanol is a strong base, which is also the reason for its caustic effect. It is of only low acute toxicity ( LD ₅₀ ( rat , oral ): 2.00 g / kg, LD ₅₀ ( rabbit , dermal ): 1.37 g / kg).

literature

National Institute of Environmental Health Sciences : Dimethylethanolamine (DMAE) [108-01-0] and Selected Salts and Esters. Review of Toxicological Literature (Update), November 2002

Trade names

Monopreparations

Risatarun (D, except trade, approval was not granted due to a lack of long-term studies)

Combination preparations

Pharmaton Vital Geriavit (CH), Vita Gerin (D)

Individual evidence

↑ Entry on DIMETHYL MEA in the CosIng database of the EU Commission, accessed on March 21, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on 2- (dimethylamino) ethanol in the GESTIS substance database of the IFA , accessed on December 22, 2019(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-198.
↑ Entry on 2-dimethylaminoethanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b Patent EP2651861B1 : Process for the production of an N, N-dialkylethanolamine with high color stability. Published on February 25, 2015 , applicant: BASF SE, inventor: Frank-Friedrich Pape, Johann-Peter Melder, Alfred Krause, Roland Bou Chedid, Martin Rudloff. ‌
↑ M. Fisman, H. Mersky, E. Helmes: Double-blind trial of 2-dimethylaminoethanol in Alzheimer's disease. In: The American journal of psychiatry. Volume 138, Number 7, July 1981, pp. 970-972, PMID 7020434 .
↑ CC PFEIFFER, EH JENNEY, W. GALLAGHER, RP SMITH, W. BEVAN, KF KILLAM, EK KILLAM, W. BLACKMORE: Stimulant effect of 2-dimethylaminoethanol; possible precursor of brain acetylcholine. In: Science. Volume 126, Number 3274, September 1957, pp. 610-611, PMID 13467254 .
↑ W. Sergio: Use of DMAE (2-dimethylaminoethanol) in the induction of lucid dreams. In: Medical Hypotheses. 26, 1988, pp. 255-257, doi : 10.1016 / 0306-9877 (88) 90129-6 .
^ R. Grossman: The role of dimethylaminoethanol in cosmetic dermatology. In: American Journal of Clinical Dermatology . Volume 6, Number 1, 2005, pp. 39-47, PMID 15675889 . (Review).
↑ I. Uhoda, N. Faska, C. Robert, G. Cauwenbergh, GE Piérard: . Split face study on the cutaneous tensile effect of 2-dimethylaminoethanol (deanol) gel In: Skin Research and Technology . Volume 8, Number 3, August 2002, pp. 164-167, PMID 12236885 .

[CosIng-1] Entry on DIMETHYL MEA in the CosIng database of the EU Commission, accessed on March 21, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on 2- (dimethylamino) ethanol in the GESTIS substance database of the IFA , accessed on December 22, 2019(JavaScript required) .

[CRC90_3_198-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-198.

[CLP_100.003.221-4] Entry on 2-dimethylaminoethanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[VERFAHREN-5] Patent EP2651861B1 : Process for the production of an N, N-dialkylethanolamine with high color stability. Published on February 25, 2015 , applicant: BASF SE, inventor: Frank-Friedrich Pape, Johann-Peter Melder, Alfred Krause, Roland Bou Chedid, Martin Rudloff. ‌

[PMID7020434-6] M. Fisman, H. Mersky, E. Helmes: Double-blind trial of 2-dimethylaminoethanol in Alzheimer's disease. In: The American journal of psychiatry. Volume 138, Number 7, July 1981, pp. 970-972, PMID 7020434 .

[PMID13467254-7] CC PFEIFFER, EH JENNEY, W. GALLAGHER, RP SMITH, W. BEVAN, KF KILLAM, EK KILLAM, W. BLACKMORE: Stimulant effect of 2-dimethylaminoethanol; possible precursor of brain acetylcholine. In: Science. Volume 126, Number 3274, September 1957, pp. 610-611, PMID 13467254 .

[DOI10.1016/0306-9877(88)90129-6-8] W. Sergio: Use of DMAE (2-dimethylaminoethanol) in the induction of lucid dreams. In: Medical Hypotheses. 26, 1988, pp. 255-257, doi : 10.1016 / 0306-9877 (88) 90129-6 .

[PMID15675889-9] R. Grossman: The role of dimethylaminoethanol in cosmetic dermatology. In: American Journal of Clinical Dermatology . Volume 6, Number 1, 2005, pp. 39-47, PMID 15675889 . (Review).

[PMID12236885-10] I. Uhoda, N. Faska, C. Robert, G. Cauwenbergh, GE Piérard: . Split face study on the cutaneous tensile effect of 2-dimethylaminoethanol (deanol) gel In: Skin Research and Technology . Volume 8, Number 3, August 2002, pp. 164-167, PMID 12236885 .