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

N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline[1]
Names
Preferred IUPAC name
Ethyl 2-ethoxyquinoline-1(2H)-carboxylate
Other names
Ethyl 1,2-dihydro-2-ethoxyquinoline-1-carboxylate
Identifiers
CAS Number
3D model (JSmol)
Abbreviations EEDQ
ChEMBL
ChemSpider
ECHA InfoCard 100.036.728
EC Number
  • 240-418-2
PubChem CID
UNII
CompTox Dashboard (EPA)
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).
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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

  1. ^ 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline at Sigma-Aldrich
  2. ^ Neuroscience Letters 1992, 137(2), p.265
  3. ^ https://www.bachem.com/
  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.


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