Diarylpropionitrile

Diarylpropionitrile (DPN), also known as 2,3-bis(p-hydroxyphenyl)propionitrile (2,3-BHPPN), is a synthetic, nonsteroidal, and highly selective agonist of ERβ (IC₅₀ = 15 nM)^[1] that is used widely in scientific research to study the function of this receptor.^[2][3] It is 70-fold more selective for ERβ over ERα,^[4] and has 100-fold lower affinity for GPER (GPR30) relative to estradiol.^[5] DPN produces antidepressant- and anxiolytic-like effects in animals via activation of the endogenous oxytocin system.^[6] First reported in 2001, DPN was the first selective ERβ agonist to be discovered, and was followed by prinaberel (ERB-041, WAY-202041), WAY-200070, and 8β-VE2 in 2004, ERB-196 (WAY-202196) in 2005, and certain phytoestrogens like liquiritigenin and nyasol (cis-hinokiresinol) since 2007.^[7]

Other namesSC-4473

CAS Number

• 1428-67-7 ^Y

PubChem CID

• 102614

ChemSpider

• 92686

Quick facts Clinical data, Other names ...

Diarylpropionitrile

Clinical data
Other names	SC-4473
Identifiers
IUPAC name 2,3-bis(4-hydroxyphenyl)propanenitrile
CAS Number	1428-67-7 Y
PubChem CID	102614
ChemSpider	92686
UNII	52XWB8Q4V8
CompTox Dashboard (EPA)	DTXSID0040387
ECHA InfoCard	100.159.105
Chemical and physical data
Formula	C15H13NO2
Molar mass	239.274 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1CC(C#N)C2=CC=C(C=C2)O)O
InChI InChI=1S/C15H13NO2/c16-10-13(12-3-7-15(18)8-4-12)9-11-1-5-14(17)6-2-11/h1-8,13,17-18H,9H2 Key:GHZHWDWADLAOIQ-UHFFFAOYSA-N

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DPN is a racemic mixture of two enantiomers, (R)-DPN and (S)-DPN. Relative to (R)-DPN, (S)-DPN has between 3- and 7-fold higher affinity for ERβ and appears to have higher intrinsic activity in activating ERβ.^[8][9] However, both enantiomers have very high affinity, potency, selectivity for ERβ and efficaciously activate ERβ.^[8] In any case, it has been suggested that (S)-DPN might be the preferred enantiomer to use for scientific research.^[8]