Diarylpropionitrile

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Diarylpropionitrile
Diarylpropionitrile.svg
Systematic (IUPAC) name
2,3-bis(4-hydroxyphenyl)propanenitrile
Identifiers
CAS Number 1428-67-7
PubChem CID: 102614
ChemSpider 92686
Synonyms SC-4473
Chemical data
Formula C15H13NO2
Molecular mass 239.26922 g/mol
  • C1=CC(=CC=C1CC(C#N)C2=CC=C(C=C2)O)O
  • 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

Diarylpropionitrile (DPN), also known as 2,3-bis(p-hydroxyphenyl)propionitrile (2,3-BHPPN), is a synthetic, non-steroidal, and highly selective agonist of ERβ (IC50 = 15 nM)[1] that is used widely in scientific research to study the function of this receptor.[1][2] It is 70-fold more selective for ERβ over ERα,[3] and has 100-fold lower affinity for GPER (GPR30) relative to estradiol.[4] DPN produces antidepressant- and anxiolytic-like effects in animals via activation of the endogenous oxytocin system.[5]

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.[6][7] However, both enantiomers have very high affinity, potency, selectivity for ERβ and efficaciously activate ERβ.[6] In any case, it has been suggested that (S)-DPN might be the preferred enantiomer to use for scientific research.[6]

See also

References

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  6. ↑ 6.0 6.1 6.2 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.



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