Dimethylethanolamine

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 ;
3D model (JSmol)	Interactive image;
Abbreviations	DMAE, DMEA
Beilstein Reference	1209235
ChEBI	CHEBI:271436 ;
ChEMBL	ChEMBL1135 ;
ChemSpider	13854944 ;
ECHA InfoCard	100.003.221
EC Number	203-542-8;
KEGG	D07777 ;
MeSH	Deanol
PubChem CID	7902;
RTECS number	KK6125000;
UNII	2N6K9DRA24 ;
UN number	2051
CompTox Dashboard (EPA)	DTXSID2020505 ;
	InChI InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3 Key: UEEJHVSXFDXPFK-UHFFFAOYSA-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)
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). verify (what is ?) Infobox references

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]

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]

References

^ Littel, RJ; Bos, M; Knoop, GJ (1990). "Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K" (PDF). Journal of Chemical and Engineering Data. 35 (3): 276–77. doi:10.1021/je00061a014. INIST 19352048.
^ Matthias Frauenkron; Johann-Peter Melder; Günther Ruider; Roland Rossbacher; Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001. ISBN 978-3-527-30673-2.
^ Ashford, Robert D. (2011). Ashford's Dictionary of Industrial Chemicals, 3rd edition. Wavelength. p. 3294. ISBN 9780952267430. OCLC 863579691. Retrieved 2023-10-04. {{cite book}}: |website= ignored (help)
^ "Dimethylaminoethyl Acrylate - Global Review 2020 to 2030". Fact.MR. Retrieved 2023-10-04.
^ Haneke, Karen E.; Masten, Scott (November 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 (PDF). National Toxicology Program (Report). Archived (PDF) from the original on 2023-10-04. Retrieved 2015-04-30 – via Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina, 27709.
^ "Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate". Archived from the original on 2023-10-04.
^ Blin, Olivier; Audebert, Christine; Pitel, Séverine; Kaladjian, Arthur; Casse-Perrot, Catherine; Zaim, Mohammed; Micallef, Joelle; Tisne-Versailles, Jacky; Sokoloff, Pierre; Chopin, Philippe; Marien, Marc (2009-12-01). "Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies". Psychopharmacology. 207 (2): 201–212. doi:10.1007/s00213-009-1648-7. ISSN 1432-2072. PMID 19756528. S2CID 8535134.
^ Levin, Edward D; Rose, Jed E; Abood, Leo (June 1995). "Effects of nicotinic dimethylaminoethyl esters on working memory performance of rats in the radial-arm maze". Pharmacology Biochemistry and Behavior. 51 (2–3): 369–373. doi:10.1016/0091-3057(94)00406-9. PMID 7667355. S2CID 20685322.

[1] Littel, RJ; Bos, M; Knoop, GJ (1990). "Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K" (PDF). Journal of Chemical and Engineering Data. 35 (3): 276–77. doi:10.1021/je00061a014. INIST 19352048.

[Ullmann-2] Matthias Frauenkron; Johann-Peter Melder; Günther Ruider; Roland Rossbacher; Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001. ISBN 978-3-527-30673-2.

[3] Ashford, Robert D. (2011). Ashford's Dictionary of Industrial Chemicals, 3rd edition. Wavelength. p. 3294. ISBN 9780952267430. OCLC 863579691. Retrieved 2023-10-04. {{cite book}}: |website= ignored (help)

[4] "Dimethylaminoethyl Acrylate - Global Review 2020 to 2030". Fact.MR. Retrieved 2023-10-04.

[5] Haneke, Karen E.; Masten, Scott (November 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 (PDF). National Toxicology Program (Report). Archived (PDF) from the original on 2023-10-04. Retrieved 2015-04-30 – via Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina, 27709.

[6] "Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate". Archived from the original on 2023-10-04.

[7] Blin, Olivier; Audebert, Christine; Pitel, Séverine; Kaladjian, Arthur; Casse-Perrot, Catherine; Zaim, Mohammed; Micallef, Joelle; Tisne-Versailles, Jacky; Sokoloff, Pierre; Chopin, Philippe; Marien, Marc (2009-12-01). "Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies". Psychopharmacology. 207 (2): 201–212. doi:10.1007/s00213-009-1648-7. ISSN 1432-2072. PMID 19756528. S2CID 8535134.

[8] Levin, Edward D; Rose, Jed E; Abood, Leo (June 1995). "Effects of nicotinic dimethylaminoethyl esters on working memory performance of rats in the radial-arm maze". Pharmacology Biochemistry and Behavior. 51 (2–3): 369–373. doi:10.1016/0091-3057(94)00406-9. PMID 7667355. S2CID 20685322.

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Dimethylethanolamine

Contents

Industrial uses

Human uses

See also

References

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 (pK_a)	9.23 (at 20 °C)^[1]
Basicity (pK_b)	4.77 (at 20 °C)
Refractive index (n_D)	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