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

N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline¹
	source ↗
Names
	Preferred IUPAC name Ethyl 2-ethoxyquinoline-1(2H)-carboxylate
	Other names Ethyl 1,2-dihydro-2-ethoxyquinoline-1-carboxylate
Identifiers
CAS Number	16357-59-8 Y;
3D model (JSmol)	Interactive image;
Abbreviations	EEDQ
ChEMBL	ChEMBL1527785;
ChemSpider	25898;
ECHA InfoCard	100.036.728
EC Number	240-418-2;
PubChem CID	27833;
UNII	60O971AN19 Y;
CompTox Dashboard (EPA)	DTXSID50871969 ;
	InChI InChI=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 Key: GKQLYSROISKDLL-UHFFFAOYSA-N;
	SMILES CCOC1C=CC2=CC=CC=C2N1C(=O)OCC;
Properties
Chemical formula	C14H17NO3
Molar mass	247.29 g/mol
Melting point	62 to 67 °C (144 to 153 °F; 335 to 340 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) is a dopamine-receptor antagonist.²

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.³

It is also an irreversible dopamine transporter (DAT) blocker in vitro, though it is ineffective in vivo.⁴

References

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline at Sigma-Aldrich
Neuroscience Letters 1992, 137(2), p.265
https://www.bachem.com/
Tarazi FI, Kula NS, Zhang K, Baldessarini RJ (August 2000). "Alkylation of rat dopamine transporters and blockade of dopamine uptake by EEDQ". Neuropharmacology. 39 (11): 2133–8. doi:10.1016/s0028-3908(00)00047-2. PMID 10963756.

[1] 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline at Sigma-Aldrich

[2] Neuroscience Letters 1992, 137(2), p.265

[3] https://www.bachem.com/

[pmid10963756-4] Tarazi FI, Kula NS, Zhang K, Baldessarini RJ (August 2000). "Alkylation of rat dopamine transporters and blockade of dopamine uptake by EEDQ". Neuropharmacology. 39 (11): 2133–8. doi:10.1016/s0028-3908(00)00047-2. PMID 10963756.

1

2

3

4