Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 13:13, 17 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit		Latest revision as of 14:18, 12 January 2024 edit undo103.153.104.62 (talk) →Industrial uses: Fixed typoTags: Mobile edit Mobile web edit
(245 intermediate revisions by more than 100 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 401999827
			| Watchedfields = changed
	| ImageFile=DMAE.png
			| verifiedrevid = 414428398
	| IUPACName=2-(Dimethylamino)ethanol
			| ImageFile = Dimethylethanolamine Structure V.1.svg
	| OtherNames=Dimethylamino ethanol<br>Deanol
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| Section1 = {{Chembox Identifiers
			| ImageSize = 160
	| Abbreviations=DMAE
			| ImageAlt = Skeletal formula of dimethylethanolamine
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ImageFile1 = Dimethylethanolamine 3D ball.png
	| ChemSpiderID = 13835861
			| ImageSize1 = 170
	| UNII_Ref = {{fdacite|correct|FDA}}
			| ImageAlt1 = Ball-and-stick model of the dimethylethanolamine molecule
	| UNII = 2N6K9DRA24
			| PIN = 2-(Dimethylamino)ethan-1-ol
	| InChIKey = CBTVGIZVANVGBH-UHFFFAOYAK
			| OtherNames = {{ubl|Deanol|Dimethyl ethanolamine|Dimethylaminoethanol|''N'',''N''-Dimethylaminoethanol|''N'',''N''-Dimethylethanolamine}}
	| ChEMBL = 122588
			|Section1={{Chembox Identifiers
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| Abbreviations = DMAE, DMEA
	| StdInChI = 1S/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3
			| CASNo = 108-01-0
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = CBTVGIZVANVGBH-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| PubChem = 7902
	| CASNo=108-01-0
			| ChemSpiderID = 13854944
	| EINECS=7902
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| PubChem=
	| SMILES = CC(C)(N)CO		| EINECS = 203-542-8
			| UNII = 2N6K9DRA24
	| InChI = 1/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNNumber = 2051
			| KEGG = D07777
			| KEGG_Ref = {{keggcite|changed|kegg}}
			| MeSHName = Deanol
			| ChEBI = 271436
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1135
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| RTECS = KK6125000
			| Beilstein = 1209235
			| SMILES = CN(C)CCO
			| StdInChI = 1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = UEEJHVSXFDXPFK-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=4|H=11|N=1|O=1		| C=4 | H=11 | N=1 | O=1
			| Appearance = Colourless liquid
	| Density=0.89 g/mL
			| Odor = Fishy, ammoniacal
	| Solubility=
			| Density = 890 mg mL<sup>−1</sup>
	| MeltingPtC = -70
			| MeltingPtK = 214.15
	| BoilingPt = 133–134 °C
			| BoilingPtK = 407.2
	| pKa=
	| pKb=		| LogP = −0.25
			| VaporPressure = 816 Pa (at 20&nbsp;°C)
	| IsoelectricPt=
			| pKa = 9.23 (at 20&nbsp;°C)<ref>{{cite journal |author1=Littel, RJ |author2=Bos, M |author3=Knoop, GJ |year=1990 |title=Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K |journal=Journal of Chemical and Engineering Data |volume=35 |issue=3 |pages=276–77 |id={{INIST|19352048}} |doi=10.1021/je00061a014 |url=https://ris.utwente.nl/ws/files/6481946/Littel90dissociation.pdf}}</ref>
	| DeltaHf=
			| pKb = 4.77 (at 20&nbsp;°C)
	| DeltaHc=
			| RefractIndex = 1.4294
	}}
	}}		}}
			|Section6={{Chembox Pharmacology
			| ATCCode_prefix = N06
			| ATCCode_suffix = BX04
			}}
			|Section7={{Chembox Hazards
			| GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}}
			| GHSSignalWord = '''DANGER'''
			| HPhrases = {{h-phrases|226|302|312|314|332}}
			| PPhrases = {{p-phrases|280|305+351+338|310}}
			| FlashPtC = 39
			| ExploLimits = 1.4–12.2%
			| LD50 = {{ubl|1.214 g/kg (dermal, rabbit)|2 g/kg (oral, rat)}}
			}}
			|Section8={{Chembox Related
			| OtherFunction_label = alkanols
			| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]}}
			| OtherCompounds = ]
			}}
			}}
			'''Dimethylethanolamine''' (DMAE or DMEA) is an ] with the formula {{chem2|(CH3)2NCH2CH2OH}}. It is ], containing both a ] and ] ]s. It is a colorless viscous liquid. It is used in skin care products for improving skin tone and
			also taken orally as a ]. It is prepared by the ] of ].<ref name=Ullmann>{{cite encyclopedia|author=Matthias Frauenkron |author2=Johann-Peter Melder |author3=Günther Ruider |author4=Roland Rossbacher |author5=Hartmut Höke |chapter=Ethanolamines and Propanolamines|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a10_001|isbn=978-3-527-30673-2}}</ref>
			==Industrial uses==
	'''Dimethylaminoethanol''', also known as '''DMAE''' or '''dimethylethanolamine''', is an ]. This compound also goes by the names of N,N-dimethyl-2-aminoethanol, beta-dimethylaminoethyl alcohol, beta-hydroxyethyldimethylamine and Deanol. It is a liquid with a color that ranges from clear to pale-yellow.
			Dimethylaminoethanol is used as a curing agent for polyurethanes and epoxy resins. It is a precursor to other chemicals, such as the ] 2-dimethylaminoethyl chloride.<ref>{{Cite book |title=Ashford's Dictionary of Industrial Chemicals, 3rd edition |isbn=9780952267430 |oclc=863579691 |date=2011 |url=https://www.worldcat.org/ |page=3294 |access-date=2023-10-04 |website=WorldCat.org |last1=Ashford |first1=Robert D. |publisher=Wavelength }}</ref> The ] ester, ] is used as a flocculating agent.<ref>{{Cite web |title=Dimethylaminoethyl Acrylate - Global Review 2020 to 2030 |url=https://www.factmr.com/report/5154/dimethylaminoethyl-acrylate-market |access-date=2023-10-04 |website=Fact.MR}}</ref>
	== Industrial uses ==
	Dimethylaminoethanol is used as a ] for ]s and ]. 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 ]stuffs, textile auxiliaries, ]s, ]s, and ]s. It is also an ] to ] removers, ] water and ] ]s. It forms a number of salts with melting points below room temperature (]) such as ''N,N''-dimethylethanolammonium acetate and ''N,N''-dimethylethanolammonium octanoate, which have been used as alternatives to conventional solvents.<ref>{{cite journal |doi=10.1021/jp906436e |author=Sanders MW, Wright L, Tate L, Fairless G, Crowhurst L, Bruce NC, Walker AJ, Hembury GA, Shimizu S |title=Unexpected preferential dehydration of artemisinin in ionic liquids |journal=J. Phys. Chem. A |volume=113 |issue=38 |pages=10143–45 |year=2009 |month=September |url=http://pubs.acs.org/doi/abs/10.1021/jp906436e |pmid=19722599}}</ref>
			Related compounds are used in gas purification, e.g. removal of ] from sour gas streams.
	== Biochemical precursor ==
	Dimethylaminoethanol is related to ] and may be a biochemical precursor to the neurotransmitter ], although this conclusion has been disputed.<ref name=Zahniser>{{cite journal |author=Zahniser NR, Chou D, Hanin I |title=Is 2-dimethylaminoethanol (deanol) indeed a precursor of brain acetylcholine? A gas chromatographic evaluation |journal=J. Pharmacol. Exp. Ther. |volume=200 |issue=3 |pages=545–59 |year=1977 |month=March |pmid=850128 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=850128}}</ref> It is believed that dimethylaminoethanol is ]ated to produce choline in the brain.<ref name=Zahniser/> It is known that dimethylaminoethanol is processed by the ] into choline; however, the choline molecule is charged and cannot pass the ].<ref name=Zahniser/>
	=== Research ===		==Human uses==
			The ] salt of DMAE, i.e. ], is sold as a dietary supplement.<ref>{{Cite report |first1=Karen E. |last1=Haneke |first2=Scott |last2=Masten |title=Dimethylethanolamine (DMAE) and Selected Salts and Esters: Review of Toxicological Literature (Update) {{!}} Report on National Institute of Environmental Health Sciences Contract No. N01-ES-65402|url=https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf |archive-url=https://web.archive.org/web/20231004110351/https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf |archive-date=2023-10-04 |url-status=live |access-date=2015-04-30 |date=November 2002 |website=National Toxicology Program |via=Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina, 27709}}</ref> It is a white powder providing 37% DMAE.<!-- 89.14/239.22 = 37.26% --><ref>{{Cite web |title=Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate |url-status=live |archive-date=2023-10-04 |archive-url=https://web.archive.org/web/20231004105534/https://www.sigmaaldrich.com/IN/en/sds/aldrich/39000 |url=https://www.sigmaaldrich.com/IN/en/sds/aldrich/39000}}</ref>
	Short-term studies have shown an increase in vigilance and alertness with a positive influence on ] following administration of DMAE, vitamins, and minerals.<ref>{{cite journal |author=Dimpfel W, Wedekind W, Keplinger I |title=Efficacy of dimethylaminoethanol (DMAE) containing vitamin-mineral drug combination on EEG patterns in the presence of different emotional states |journal=Eur. J. Med. Res. |volume=8 |issue=5 |pages=183–91 |year=2003 |month=May |pmid=12844472 }}</ref> Research for ] (ADHD) has been promising, though inconclusive.<ref>{{cite journal |author=Knobel M |title=Approach to a combined pharmacologic therapy of childhood hyperkinesis |journal=Behav Neuropsychiatry |volume=6 |issue=1-12 |pages=87–90 |year=1974 |pmid=4619768 }}</ref> Long-term studies are equivocal. Some showed dimethylaminoethanol to increase the lifespan of animals in which it was tested, while others indicate a possible reduction in the ] of ].<ref>{{cite journal |author=Cherkin A, Exkardt MJ |title=Effects of dimethylaminoethanol upon life-span and behavior of aged Japanese quail |journal=J Gerontol |volume=32 |issue=1 |pages=38–45 |year=1977 |month=January |pmid=830732 |url=http://geronj.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=830732}}</ref>
			Animal tests show possible benefit for improving ]<ref>{{Cite journal |last1=Blin |first1=Olivier |last2=Audebert |first2=Christine |last3=Pitel |first3=Séverine |last4=Kaladjian |first4=Arthur |last5=Casse-Perrot |first5=Catherine |last6=Zaim |first6=Mohammed |last7=Micallef |first7=Joelle |last8=Tisne-Versailles |first8=Jacky |last9=Sokoloff |first9=Pierre |last10=Chopin |first10=Philippe |last11=Marien |first11=Marc |date=2009-12-01 |title=Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies |url=https://link.springer.com/article/10.1007/s00213-009-1648-7 |journal=Psychopharmacology |language=en |volume=207 |issue=2 |pages=201–212 |doi=10.1007/s00213-009-1648-7 |pmid=19756528 |s2cid=8535134 |issn=1432-2072}}</ref> and ].<ref>{{Cite journal |last1=Levin |first1=Edward D |last2=Rose |first2=Jed E |last3=Abood |first3=Leo |date=June 1995 |title=Effects of nicotinic dimethylaminoethyl esters on working memory performance of rats in the radial-arm maze |url=https://www.sciencedirect.com/science/article/abs/pii/0091305794004069 |journal=Pharmacology Biochemistry and Behavior |language=en |volume=51 |issue=2–3 |pages=369–373 |doi=10.1016/0091-3057(94)00406-9|pmid=7667355 |s2cid=20685322 }}</ref>
	==See also==		==See also==
	*]		* ]
	*]		* ]
	*]		* ]
			* ]
			* ] (Centrophenoxine)
			* ]
	==References==		==References==
	{{Reflist}}		{{Reflist}}
	===Studies===
	*Earliest research
	*:{{cite journal |author=Pfeiffer CC, Jenney EH, Gallagher W, ''et al.'' |title=Stimulant effect of 2-dimethylaminoethanol; possible precursor of brain acetylcholine |journal=Science |volume=126 |issue=3274 |pages=610–1 |year=1957 |month=September |pmid=13467254 |url=http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=13467254 |doi=10.1126/science.126.3274.610}}
	*As a treatment for ]
	*:{{cite journal |author=Haug BA, Holzgraefe M |title=Orofacial and respiratory tardive dyskinesia: potential side effects of 2-dimethylaminoethanol (deanol)? |journal=Eur. Neurol. |volume=31 |issue=6 |pages=423–5 |year=1991 |pmid=1756771 |doi=10.1159/000116708 }}
			]
	*As an unsuccessful treatment for ]
			]
	*:{{cite journal |author=Fisman M, Mersky H, Helmes E |title=Double-blind trial of 2-dimethylaminoethanol in Alzheimer's disease |journal=Am J Psychiatry |volume=138 |issue=7 |pages=970–2 |year=1981 |month=July |pmid=7020434 |url=http://ajp.psychiatryonline.org/cgi/pmidlookup?view=long&pmid=7020434}}
			]
	{{Dietary_supplements}}
	{{Nootropics}}
	{{Cholinergics}}
	]
	]
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]