Dimethylethanolamine

Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH₃)₂NCH₂CH₂OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care products for improving skin tone and also taken orally as a nootropic. It is prepared by the ethoxylation of dimethylamine.^[2]

Dimethylethanolamine

Names
Preferred IUPAC name 2-(Dimethylamino)ethan-1-ol
Other names Deanol Dimethyl ethanolamine Dimethylaminoethanol N,N-Dimethylaminoethanol N,N-Dimethylethanolamine
Identifiers
CAS Number	108-01-0 Y
3D model (JSmol)	Interactive image
Abbreviations	DMAE, DMEA
Beilstein Reference	1209235
ChEBI	CHEBI:271436 N
ChEMBL	ChEMBL1135 N
ChemSpider	13854944 N
ECHA InfoCard	100.003.221
EC Number	203-542-8
KEGG	D07777 N
MeSH	Deanol
PubChem CID	7902
RTECS number	KK6125000
UNII	2N6K9DRA24 Y
UN number	2051
CompTox Dashboard (EPA)	DTXSID2020505
InChI InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3 N Key: UEEJHVSXFDXPFK-UHFFFAOYSA-N N
SMILES CN(C)CCO
Properties
Chemical formula	C4H11NO
Molar mass	89.138 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
Pharmacology
ATC code	N06BX04 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H312, H314, H332
Precautionary statements	P280, P305+P351+P338, P310
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 (dermal, rabbit) 2 g/kg (oral, rat)
Related compounds
Related alkanols	N-Methylethanolamine Diethylethanolamine Diethanolamine N,N-Diisopropylaminoethanol Methyl diethanolamine Triethanolamine Bis-tris methane
Related compounds	Diethylhydroxylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Industrial uses

Dimethylaminoethanol is used as a curing agent for polyurethanes and epoxy resins. It is a precursor to other chemicals, such as the nitrogen mustard 2-dimethylaminoethyl chloride.^[3] The acrylate ester, dimethylaminoethyl acrylate is used as a flocculating agent.^[4]

Related compounds are used in gas purification, e.g. removal of hydrogen sulfide from sour gas streams.

Human uses

The bitartrate salt of DMAE, i.e. N,N-dimethylethanolamine bitartrate, is sold as a dietary supplement.^[5] It is a white powder providing 37% DMAE.^[6]

Animal tests show possible benefit for improving spatial memory^[7] and working memory.^[8]

See also

• Choline
• Diphenhydramine
• Doxylamine
• Ethanolamine
• Meclofenoxate (Centrophenoxine)
• Orphenadrine