N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

{{DISPLAYTITLE:''N''-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline}} {{chembox | Watchedfields = changed | verifiedrevid = 424811563 | Reference =<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/149837 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline] at [[Sigma-Aldrich]]</ref> | Name = ''N''-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline | ImageFile = EEDQ Structure.svg | ImageSize = | PIN =Ethyl 2-ethoxyquinoline-1(2''H'')-carboxylate | OtherNames =Ethyl 1,2-dihydro-2-ethoxyquinoline-1-carboxylate |Section1={{Chembox Identifiers | Abbreviations = EEDQ | CASNo_Ref = {{cascite|correct|??}} | CASNo =16357-59-8 | ChEMBL = 1527785 | ChemSpiderID = 25898 | EC_number = 240-418-2 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 60O971AN19 | PubChem =27833 | StdInChI=1S/C14H17NO3/c1-3-17-13-10-9-11-7-5-6-8-12(11)15(13)14(16)18-4-2/h5-10,13H,3-4H2,1-2H3 | StdInChIKey = GKQLYSROISKDLL-UHFFFAOYSA-N | SMILES =CCOC1C=CC2=CC=CC=C2N1C(=O)OCC }} |Section2={{Chembox Properties | Formula =C14H17NO3 | MolarMass =247.29 g/mol | Appearance = | Density = | MeltingPtC = 62 to 67 | MeltingPt_notes = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''''N''-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline''' ('''EEDQ''') is a dopamine-receptor antagonist.<ref>''Neuroscience Letters'' 1992, 137(2), p.265</ref>

EEDQ is also a highly specific reagent for carboxyl groups. It enables the coupling of acylamino acids with amino acid esters in high yield and without racemization.<ref>''https://www.bachem.com/''</ref>

It is also an irreversible [[dopamine transporter]] (DAT) [[dopamine reuptake inhibitor|blocker]] ''[[in vitro]]'', though it is ineffective ''[[in vivo]]''.<ref name="pmid10963756">{{cite journal | vauthors = Tarazi FI, Kula NS, Zhang K, Baldessarini RJ | title = Alkylation of rat dopamine transporters and blockade of dopamine uptake by EEDQ | journal = Neuropharmacology | volume = 39 | issue = 11 | pages = 2133–8 | date = August 2000 | pmid = 10963756 | doi = 10.1016/s0028-3908(00)00047-2 | url = }}</ref>

==References== {{reflist}}

{{DEFAULTSORT:Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, N-}} [[Category:Carbamates]] [[Category:Quinolines]] [[Category:Ethoxy compounds]] [[Category:Ethyl esters]]