DPA-714

DPA-714 or N,N-diethyl-2-[4-(2-fluoroethoxy)phenyl]-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-acetamide is a selective ligand for the translocator protein (TSPO) currently under evaluation for several clinical applications.^[1] For this reason, a practical, multigram synthetic route for its preparation has been described.^[2]

CAS Number

• 958233-07-3

ChemSpider

• 23328478

UNII

• Y1H4D2VKZD

ChEMBL

• ChEMBL512306

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DPA-714

Identifiers
IUPAC name N,N-diethyl-2-[4-(2-fluoroethoxy)phenyl]-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-acetamide
CAS Number	958233-07-3
ChemSpider	23328478
UNII	Y1H4D2VKZD
ChEMBL	ChEMBL512306
Chemical and physical data
Formula	C22H27FN4O2
Molar mass	398.482 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)C(=O)Cc1c(nn2c1nc(cc2C)C)c3ccc(cc3)OCCF
InChI InChI=1S/C22H27FN4O2/c1-5-26(6-2)20(28)14-19-21(17-7-9-18(10-8-17)29-12-11-23)25-27-16(4)13-15(3)24-22(19)27/h7-10,13H,5-6,11-12,14H2,1-4H3 Key:FLZZFWBNYJNHMY-UHFFFAOYSA-N

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The binding affinity of DPA-714 for TSPO is reported as K_i = 7.0 ± 0.4 nM.^[3][4]

[¹⁸F]DPA-714 is currently under investigation as a potential radiopharmaceutical for imaging TSPO in living systems using positron emission tomography (PET). DPA-714, along with other members of the DPA class of TSPO ligands, has been shown to decrease microglial activation and increase neuronal survival in a quinolinic acid rat model of excitotoxic neurodegeneration, suggesting potential neuroprotective effects.^[5]