Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:41 UTC
Update Date2023-02-21 17:23:50 UTC
HMDB IDHMDB0033971
Secondary Accession Numbers
  • HMDB33971
Metabolite Identification
Common Name2-Diethylaminoethanol
Description2-Diethylaminoethanol, also known as diethylethanolamine or DEAE, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Based on a literature review a significant number of articles have been published on 2-Diethylaminoethanol.
Structure
Data?1677000230
Synonyms
ValueSource
beta-(Diethylamino)ethyl alcoholChEBI
beta-HydroxytriethylamineChEBI
DEAEChEBI
Diethyl(2-hydroxyethyl)amineChEBI
DiethylaminoethanolChEBI
DiethylethanolamineChEBI
DiethylmonoethanolamineChEBI
N,N-Diethyl-2-aminoethanolChEBI
N,N-Diethyl-N-(beta-hydroxyethyl)amineChEBI
N,N-DiethylethanolamineChEBI
b-(Diethylamino)ethyl alcoholGenerator
Β-(diethylamino)ethyl alcoholGenerator
b-HydroxytriethylamineGenerator
Β-hydroxytriethylamineGenerator
N,N-Diethyl-N-(b-hydroxyethyl)amineGenerator
N,N-Diethyl-N-(β-hydroxyethyl)amineGenerator
2-(N,N-Dimethylamino)ethanol hydrochlorideMeSH
2-(Dimethylamino)ethanol hydrochlorideMeSH
2-Diethylaminoethanol hydrochlorideMeSH
2-Diethylaminoethanol hydrochloride, 14C-labeledMeSH
2-Diethylaminoethanol sulfate (2:1)MeSH
2-Diethylaminoethanol tartrateMeSH
2-Diethylaminoethanol, sodium saltMeSH
Deanol hydrochlorideMeSH
Ethanol, 2-(dimethylamino)-, hydrochloride (1:1)MeSH
Ethanol, 2-dimethylamino-, hydrochlorideMeSH
(2-Hydroxyethyl)diethylamineHMDB
(diethylamino)EthanolHMDB
-DiethylaminoHMDB
2-(diethylamino)-EthanolHMDB
2-(diethylamino)EthanolHMDB
2-(diethylamino)Ethyl alcoholHMDB
2-(N,N-diethylamino)EthanolHMDB
2-DiethylaminoHMDB
2-diethylamino-EthanolHMDB
2-Diethylaminoethanol, 9ciHMDB
2-HydroxytriethylamineHMDB
2-N-(diethylamino)EthanolHMDB
2-N-DiethylaminoethanolHMDB
beta-(diethylamino)EthanolHMDB
beta-DiethylaminoethanolHMDB
beta-Diethylaminoethyl alcoholHMDB
DehydasalHMDB
DiaethylaminoaethanolHMDB
diethylamino EthanolHMDB
ETHANOL,2-diethylaminoHMDB
N, N-DiethylethanolamineHMDB
N,N-Diethyl-2-hydroxyethylamineHMDB
N,N-DiethylaminoethanolHMDB
N,N-DiethylmonoethanolamineHMDB
N-(diethylamino)EthanolHMDB
N-DiethylaminoethanolHMDB
Pennad 150HMDB
PerdilatonHMDB
Chemical FormulaC6H15NO
Average Molecular Weight117.1894
Monoisotopic Molecular Weight117.115364107
IUPAC Name2-(diethylamino)ethan-1-ol
Traditional NameDEAE
CAS Registry Number100-37-8
SMILES
CCN(CC)CCO
InChI Identifier
InChI=1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3
InChI KeyBFSVOASYOCHEOV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point163.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP0.050 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility665 g/LALOGPS
logP0.56ALOGPS
logP0.21ChemAxon
logS0.75ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.78 m³·mol⁻¹ChemAxon
Polarizability14.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.09231661259
DarkChem[M-H]-118.64131661259
DeepCCS[M+H]+127.86530932474
DeepCCS[M-H]-125.25430932474
DeepCCS[M-2H]-161.53230932474
DeepCCS[M+Na]+136.45130932474
AllCCS[M+H]+129.232859911
AllCCS[M+H-H2O]+125.132859911
AllCCS[M+NH4]+133.132859911
AllCCS[M+Na]+134.232859911
AllCCS[M-H]-130.232859911
AllCCS[M+Na-2H]-133.732859911
AllCCS[M+HCOO]-137.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-DiethylaminoethanolCCN(CC)CCO1624.7Standard polar33892256
2-DiethylaminoethanolCCN(CC)CCO895.0Standard non polar33892256
2-DiethylaminoethanolCCN(CC)CCO891.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Diethylaminoethanol,1TMS,isomer #1CCN(CC)CCO[Si](C)(C)C1052.6Semi standard non polar33892256
2-Diethylaminoethanol,1TBDMS,isomer #1CCN(CC)CCO[Si](C)(C)C(C)(C)C1273.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-679642371f35e680a2162017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-c65d76d5528026f7e7162017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol CI-B (Non-derivatized)splash10-014i-0900000000-798a98f8899d79a390442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-0e3e36718a949839e4ca2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-4babed528318afee12022017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-419afeeab276c9a36e302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-679642371f35e680a2162018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-c65d76d5528026f7e7162018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol CI-B (Non-derivatized)splash10-014i-0900000000-798a98f8899d79a390442018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-0e3e36718a949839e4ca2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-4babed528318afee12022018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Diethylaminoethanol EI-B (Non-derivatized)splash10-000i-9000000000-419afeeab276c9a36e302018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Diethylaminoethanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9000000000-8635568927d2a02724b12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Diethylaminoethanol GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9200000000-772be939fd33e13941f32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Diethylaminoethanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 10V, Positive-QTOFsplash10-014i-1900000000-0d3d077e3c625a02f1332015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 20V, Positive-QTOFsplash10-0uxr-4900000000-0ff07e3595583a2fec8a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 40V, Positive-QTOFsplash10-00fr-9100000000-68f36287c0225874fcf42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 10V, Negative-QTOFsplash10-014i-4900000000-ad21c23f9f507797f9ba2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 20V, Negative-QTOFsplash10-014i-9600000000-58b1e4dfbbe5b6ee32652015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 40V, Negative-QTOFsplash10-006x-9000000000-8bc79a57309fabe0e4892015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 10V, Positive-QTOFsplash10-0uxr-1900000000-875cd6dae71978dc1f4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 20V, Positive-QTOFsplash10-0udi-0900000000-8ab050f625b59a8524552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 40V, Positive-QTOFsplash10-0uk9-9500000000-191e1b59f0e0845c2eb92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 10V, Negative-QTOFsplash10-014i-0900000000-8749507c5f3ff7c4c1e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 20V, Negative-QTOFsplash10-00kb-9500000000-0b41fe27133c03c813cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Diethylaminoethanol 40V, Negative-QTOFsplash10-0006-9000000000-154488c2ba6e0c06d07d2021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012202
KNApSAcK IDNot Available
Chemspider ID13842001
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Diethylaminoethanol
METLIN IDNot Available
PubChem Compound7497
PDB IDNot Available
ChEBI ID52153
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1263071
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yang DC, Goldstin B, Moormann AE, Flynn DL, Gullikson GW: SC-53606, a potent and selective antagonist of 5-hydroxytryptamine4 receptors in isolated rat esophageal tunica muscularis mucosae. J Pharmacol Exp Ther. 1993 Sep;266(3):1339-47. [PubMed:8396633 ]
  2. Lee SE, Lee CG, Kang DH, Lee HY, Jung KH: Preparation of corncob grits as a carrier for immobilizing yeast cells for ethanol production. J Microbiol Biotechnol. 2012 Dec;22(12):1673-80. [PubMed:23221530 ]
  3. Mazumder A, Kumar A, Purohit AK, Dubey DK: Application of high performance liquid chromatography coupled to on-line solid-phase extraction-nuclear magnetic resonance spectroscopy for the analysis of degradation products of V-class nerve agents and nitrogen mustard. J Chromatogr A. 2010 Apr 23;1217(17):2887-94. doi: 10.1016/j.chroma.2010.02.071. Epub 2010 Mar 3. [PubMed:20303089 ]
  4. Bhiri F, Chaabouni SE, Limam F, Ghrir R, Marzouki N: Purification and biochemical characterization of extracellular beta-glucosidases from the hypercellulolytic Pol6 mutant of Penicillium occitanis. Appl Biochem Biotechnol. 2008 May;149(2):169-82. doi: 10.1007/s12010-008-8146-y. Epub 2008 Mar 4. [PubMed:18401747 ]
  5. Zhang R, Mjoseng HK, Hoeve MA, Bauer NG, Pells S, Besseling R, Velugotla S, Tourniaire G, Kishen RE, Tsenkina Y, Armit C, Duffy CR, Helfen M, Edenhofer F, de Sousa PA, Bradley M: A thermoresponsive and chemically defined hydrogel for long-term culture of human embryonic stem cells. Nat Commun. 2013;4:1335. doi: 10.1038/ncomms2341. [PubMed:23299885 ]
  6. Feng G, Jiang L, Wen P, Cui Y, Li H, Hu D: A new ion-exchange adsorbent with paramagnetic properties for the separation of genomic DNA. Analyst. 2011 Nov 21;136(22):4822-9. doi: 10.1039/c1an15149e. Epub 2011 Oct 3. [PubMed:21966668 ]
  7. Iwasaki Y, Ichikawa Y, Igarashi O, Konno S, Aoyagi J, Ikeda K, Marabuchi S, Ono S, Iguchi H, Kawabe K, Fujioka T: T-588 protects motor neuron death following axotomy. Neurochem Res. 2004 Feb;29(2):403-6. [PubMed:15002737 ]
  8. Oitate M, Hirota T, Takahashi M, Murai T, Miura S, Senoo A, Hosokawa T, Oonishi T, Ikeda T: Mechanism for covalent binding of rofecoxib to elastin of rat aorta. J Pharmacol Exp Ther. 2007 Mar;320(3):1195-203. Epub 2006 Dec 12. [PubMed:17164475 ]
  9. Takahashi Y, Yasui TA, Stauber EJ, Hippler M: Comparison of the subunit compositions of the PSI-LHCI supercomplex and the LHCI in the green alga Chlamydomonas reinhardtii. Biochemistry. 2004 Jun 22;43(24):7816-23. [PubMed:15196024 ]
  10. Luong J, Shellie RA, Cortes H, Gras R, Hayward T: Ultra-trace level analysis of morpholine, cyclohexylamine, and diethylaminoethanol in steam condensate by gas chromatography with multi-mode inlet, and flame ionization detection. J Chromatogr A. 2012 Mar 16;1229:223-9. doi: 10.1016/j.chroma.2012.01.041. Epub 2012 Jan 24. [PubMed:22325017 ]
  11. Lesch HP, Laitinen A, Peixoto C, Vicente T, Makkonen KE, Laitinen L, Pikkarainen JT, Samaranayake H, Alves PM, Carrondo MJ, Yla-Herttuala S, Airenne KJ: Production and purification of lentiviral vectors generated in 293T suspension cells with baculoviral vectors. Gene Ther. 2011 Jun;18(6):531-8. doi: 10.1038/gt.2010.162. Epub 2011 Jan 20. [PubMed:21248790 ]
  12. Molaakbari E, Mostafavi A, Afzali D: Ionic liquid ultrasound assisted dispersive liquid-liquid microextraction method for preconcentration of trace amounts of rhodium prior to flame atomic absorption spectrometry determination. J Hazard Mater. 2011 Jan 30;185(2-3):647-52. doi: 10.1016/j.jhazmat.2010.09.067. Epub 2010 Sep 29. [PubMed:20971554 ]
  13. Dong WK, Chen X, Sun YX, Yang YH, Zhao L, Xu L, Yu TZ: Synthesis, structure and spectroscopic properties of two new trinuclear nickel(II) clusters possessing solvent effect. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Oct 15;74(3):719-25. doi: 10.1016/j.saa.2009.08.037. Epub 2009 Aug 20. [PubMed:19740699 ]
  14. Jung H, Seok SH, Han JH, Abdelkader TS, Kim TH, Chang SN, Ko AS, Choi SK, Lee CR, Seo JE, Byun SH, Kim JA, Park JH: Effect of fluorescent whitening agent on the transcription of cell damage-related genes in zebrafish embryos. J Appl Toxicol. 2012 Sep;32(9):654-61. doi: 10.1002/jat.1665. Epub 2011 May 2. [PubMed:21538407 ]
  15. Gais HJ, Bruns PR, Raabe G, Hainz R, Schleusner M, Runsink J, Babu GS: Dynamic behavior of chiral sulfonimidoyl-substituted allyl and alkyl (dimethylamino)titanium(IV) complexes: metallotropic shift, reversible beta-hydride elimination/reinsertion, and ab initio calculations of allyl and alkyl aminosulfoxonium ylides. J Am Chem Soc. 2005 May 11;127(18):6617-31. [PubMed:15869283 ]
  16. Smilkstein M, Sriwilaijaroen N, Kelly JX, Wilairat P, Riscoe M: Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening. Antimicrob Agents Chemother. 2004 May;48(5):1803-6. [PubMed:15105138 ]
  17. Ruchelman AL, Singh SK, Ray A, Wu X, Yang JM, Zhou N, Liu A, Liu LF, LaVoie EJ: 11H-Isoquino[4,3-c]cinnolin-12-ones; novel anticancer agents with potent topoisomerase I-targeting activity and cytotoxicity. Bioorg Med Chem. 2004 Feb 15;12(4):795-806. [PubMed:14759740 ]
  18. Hossain MB, Symersky J, Neely SC, van der Helm D, Magarian RA: Structure of 1-(4-[2-(diethylamino)ethoxy]phenyl)-2-(4-methoxyphenyl)-1-phenylethan- 1-ol, the non-steroidal antiestrogen MER25. Acta Crystallogr C. 1993 Mar 15;49 ( Pt 3):500-4. [PubMed:8484922 ]
  19. Kedderis GL, Batra R, Koop DR: Epoxidation of acrylonitrile by rat and human cytochromes P450. Chem Res Toxicol. 1993 Nov-Dec;6(6):866-71. [PubMed:8117926 ]
  20. Jan CR, Ho CM, Wu SN, Tseng CJ: Bradykinin-evoked Ca2+ mobilization in Madin Darby canine kidney cells. Eur J Pharmacol. 1998 Aug 21;355(2-3):219-33. [PubMed:9760037 ]
  21. Nesterov VN, Nesterov VV: Polymorphism and solvolysis of 2-cyano-3-[4-(N,N-diethylamino)phenyl]prop-2-enethioamide. Acta Crystallogr C. 2004 Nov;60(Pt 11):o781-5. Epub 2004 Oct 9. [PubMed:15528819 ]
  22. Vidic J, Podgornik A, Jancar J, Frankovic V, Kosir B, Lendero N, Cucek K, Krajnc M, Strancar A: Chemical and chromatographic stability of methacrylate-based monolithic columns. J Chromatogr A. 2007 Mar 9;1144(1):63-71. Epub 2006 Dec 4. [PubMed:17141793 ]
  23. Sindhu R, Tiwari AK, Mishra LC, Husain MM: Spectroscopic interaction of a coumarin derivative with bovine serum albumin. Cancer Biother Radiopharm. 2012 Sep;27(7):452-6. doi: 10.1089/cbr.2012.1180. [PubMed:22947088 ]
  24. UNGER H: [Effect of diethylaminoethanol (dehydasal) on blood sugar]. Dtsch Gesundheitsw. 1951 Jun 21;6(25):706-8; contd. [PubMed:14849357 ]
  25. Hardick O, Dods S, Stevens B, Bracewell DG: Nanofiber adsorbents for high productivity downstream processing. Biotechnol Bioeng. 2013 Apr;110(4):1119-28. doi: 10.1002/bit.24765. Epub 2012 Nov 1. [PubMed:23097054 ]
  26. Cody V, Luft J: Structure-activity relationships of antiarrhythmic agents: crystal structure of amiodarone hydrochloride and two derivatives, and their conformational comparison with thyroxine. Acta Crystallogr B. 1989 Apr 1;45 ( Pt 2):172-8. [PubMed:2619958 ]
  27. Bandeira V, Peixoto C, Rodrigues AF, Cruz PE, Alves PM, Coroadinha AS, Carrondo MJ: Downstream processing of lentiviral vectors: releasing bottlenecks. Hum Gene Ther Methods. 2012 Aug;23(4):255-63. doi: 10.1089/hgtb.2012.059. Epub 2012 Aug 30. [PubMed:22934827 ]
  28. Karim MZ, Gu Z, Sawada A, Taniguchi T, Kawase K, Yamamoto T, Kitazawa Y: Neuroprotective effects of R(-)-1-(benzo[b]thiophen-5-yl)-2- [2-(N,N-diethylamino)ethoxy]ethanol hydrochloride (T-588) against retinal ganglion cell death induced by elevated intraocular pressure in rat. Jpn J Ophthalmol. 2002 Nov-Dec;46(6):621-6. [PubMed:12543187 ]
  29. Ulrich G, Ziessel R, Haefele A: A general synthetic route to 3,5-substituted boron dipyrromethenes: applications and properties. J Org Chem. 2012 May 4;77(9):4298-311. doi: 10.1021/jo3002408. Epub 2012 Apr 23. [PubMed:22497543 ]
  30. Vazquez SR, Rodriguez MC, Mosquera M, Rodriguez-Prieto F: Rotamerism, tautomerism, and excited-state intramolecular proton transfer in 2-(4'-N,N-diethylamino-2'-hydroxyphenyl)benzimidazoles: novel benzimidazoles undergoing excited-state intramolecular coupled proton and charge transfer. J Phys Chem A. 2008 Jan 24;112(3):376-87. Epub 2007 Dec 23. [PubMed:18154323 ]
  31. Dimmock JR, Vashishtha SC, Quail JW, Pugazhenthi U, Zimpel Z, Sudom AM, Allen TM, Kao GY, Balzarini J, De Clercq E: 4-(beta-Arylvinyl)-3-(beta-arylvinylketo)-1-ethyl-4-piperidinols and related compounds: a novel class of cytotoxic and anticancer agents. J Med Chem. 1998 Oct 8;41(21):4012-20. [PubMed:9767639 ]
  32. SILVESTRINI B, CATANESE B, GARAU A, POZZATTI C: TOXICITY STUDIES ON 3-PHENYL-5-BETADIETHYLAMINOETHYL-1,2,4-OXADIAZOLE: VESICAL IRRITATING ACTIVITY OF DIETHYLAMINE AND OTHER SIMPLE AMINES. Exp Mol Pathol Suppl. 1963 Dec;2:41-9. [PubMed:14089664 ]
  33. Matsumura K, Mitsui Y, Sato K, Sakamoto M, Aoki Y: Schistosoma mansoni: possible involvement of protein kinase C in linoleic acid-induced proteolytic enzyme release from cercariae. Exp Parasitol. 1991 Apr;72(3):311-20. [PubMed:2015870 ]
  34. Mishra R, Sjolander D, Hammarstrom P: Spectroscopic characterization of diverse amyloid fibrils in vitro by the fluorescent dye Nile red. Mol Biosyst. 2011 Apr;7(4):1232-40. doi: 10.1039/c0mb00236d. Epub 2011 Jan 31. [PubMed:21279219 ]
  35. Ngai PH, Ng TB: A lectin with antifungal and mitogenic activities from red cluster pepper (Capsicum frutescens) seeds. Appl Microbiol Biotechnol. 2007 Feb;74(2):366-71. Epub 2006 Nov 3. [PubMed:17082928 ]
  36. Grover A, Dwivedy I, Singh AK, Ray S, Singh MM, Kamboj VP: Synthesis and pregnancy-inhibiting activity of 7-substituted androst-5-ene derivatives. Steroids. 1991 Sep;56(9):477-80. [PubMed:1805460 ]
  37. Kudan S, Pichyangkura R: Purification and characterization of thermostable chitinase from Bacillus licheniformis SK-1. Appl Biochem Biotechnol. 2009 Apr;157(1):23-35. doi: 10.1007/s12010-008-8328-7. Epub 2009 Feb 4. [PubMed:19190863 ]
  38. Nagai H, Yakuo I, Arimura A, Choi SH, Inagaki N, Koda A: Anti-asthmatic activity of newly synthesized calcium antagonists: 2-n-butyl-1 (N-methyl-n-[2-(N',N'-dimethylamino)ethyl]amino) -5,6-methylenedioxy-indene and -indane. Int Arch Allergy Appl Immunol. 1989;90(2):137-43. [PubMed:2583850 ]
  39. Menicagli S, Lippi A, Criscuoli M, Gervasi PG: Effect of rociverine on P450-dependent monooxygenases and its N-deethylation metabolism in rat liver microsomes. Biochem Pharmacol. 1993 Mar 9;45(5):1097-105. [PubMed:8461039 ]
  40. UNGER H: [Fractional stomach aspiration with diethylaminoethanol (Dehydasal)]. Dtsch Gesundheitsw. 1951 Mar 8;6(10):284. [PubMed:14822695 ]
  41. MATTHEWS JH, TERRY RT: Histoplasmosis: treatment of two cases with betadiethylaminoethyl fencholate. Dis Chest. 1956 Nov;30(5):570-5. [PubMed:13365509 ]
  42. Enokibara S: Purification and characterization of an alkaliphilic choline oxidase of Fusarium oxysporum. Biosci Biotechnol Biochem. 2012;76(12):2219-24. Epub 2012 Dec 7. [PubMed:23221722 ]
  43. Qu W, Ikejima K, Zhong Z, Waalkes MP, Thurman RG: Glycine blocks the increase in intracellular free Ca2+ due to vasoactive mediators in hepatic parenchymal cells. Am J Physiol Gastrointest Liver Physiol. 2002 Dec;283(6):G1249-56. Epub 2002 Aug 14. [PubMed:12388211 ]
  44. Kaneta T, Yamamoto D, Imasaka T: Postcolumn derivatization of proteins in capillary sieving electrophoresis/laser-induced fluorescence detection. Electrophoresis. 2009 Nov;30(21):3780-5. doi: 10.1002/elps.200900314. [PubMed:19862753 ]
  45. SOEHRING K, STAVE U: [The effect of novocain (procaine) and diethylaminoethanol on the isolated phrenicus-diaphragma preparation of the rat]. Arch Int Pharmacodyn Ther. 1951 Feb;85(3-4):288-305. [PubMed:14830345 ]
  46. Iglesias E: Inclusion complexation of novocaine by beta-cyclodextrin in aqueous solutions. J Org Chem. 2006 Jun 9;71(12):4383-92. [PubMed:16749765 ]
  47. Nyeborg M, Pissavini M, Lemasson Y, Doucet O: Validation of HPLC method for the simultaneous and quantitative determination of 12 UV-filters in cosmetics. Int J Cosmet Sci. 2010 Feb;32(1):47-53. doi: 10.1111/j.1468-2494.2009.00544.x. [PubMed:20412202 ]
  48. Welsh JP, Yamaguchi H, Zeng XH, Kojo M, Nakada Y, Takagi A, Sugimori M, Llinas RR: Normal motor learning during pharmacological prevention of Purkinje cell long-term depression. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17166-71. Epub 2005 Nov 8. [PubMed:16278298 ]
  49. Cippitelli A, Rezvani AH, Robinson JE, Eisenberg L, Levin ED, Bonaventure P, Motley ST, Lovenberg TW, Heilig M, Thorsell A: The novel, selective, brain-penetrant neuropeptide Y Y2 receptor antagonist, JNJ-31020028, tested in animal models of alcohol consumption, relapse, and anxiety. Alcohol. 2011 Sep;45(6):567-76. doi: 10.1016/j.alcohol.2010.09.003. Epub 2010 Dec 10. [PubMed:21145691 ]
  50. Qiu X, Ren X, Hu S: Fabrication of dual-responsive cellulose-based membrane via simplified surface-initiated ATRP. Carbohydr Polym. 2013 Feb 15;92(2):1887-95. doi: 10.1016/j.carbpol.2012.11.080. Epub 2012 Dec 3. [PubMed:23399233 ]
  51. Qu JB, Wan XZ, Zhai YQ, Zhou WQ, Su ZG, Ma GH: A novel stationary phase derivatized from hydrophilic gigaporous polystyrene-based microspheres for high-speed protein chromatography. J Chromatogr A. 2009 Sep 11;1216(37):6511-6. doi: 10.1016/j.chroma.2009.07.059. Epub 2009 Aug 3. [PubMed:19665720 ]
  52. Torres GE, Holt IL, Andrade R: Antagonists of 5-HT4 receptor-mediated responses in adult hippocampal neurons. J Pharmacol Exp Ther. 1994 Oct;271(1):255-61. [PubMed:7965722 ]
  53. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .