Diarylpropionitrile
Chemical compound From Wikipedia, the free encyclopedia
Chemical compound From Wikipedia, the free encyclopedia
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]
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Other names | SC-4473 |
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ECHA InfoCard | 100.159.105 |
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Formula | C15H13NO2 |
Molar mass | 239.274 g·mol−1 |
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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]
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