Biochanin A

- Overview
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    Background
    
    IC50: 1.8, 1.4 and 2.4 μM for mouse, rat and human FAAH, respectivelyBiochanin A is a natural inhibitor of fatty acid amide hydrolase. Inhibitors of fatty acid amide hydrolase (FAAH), which responsible for the metabolism of the endogenous cannabinoid (CB) receptor ligand anandamide (AEA), are effective in a number of animal models of pain.In vitro: Biochanin A was found to be the most promising candidate. Biochanin A inhibited the hydrolysis of 0.5 mM AEA by mouse, rat and human FAAH with IC50 values of 1.8, 1.4 and 2.4 μM respectively. Biochanin A was found to not interact to any extent with CB1 or CB2 receptors, nor with FAAH-2 [1]. In vivo: In anaesthetized mice, both URB597 and biochanin A inhibited the spinal phosphorylation of extracellular signal-regulated kinase caused by the intraplantar injection of formalin. The effects of both URB597 and biochanin A were found to be significantly reduced by the CB1 receptor antagonist/inverse agonist AM251. In addition, in the tetrad test, biochanin A did not increase brain AEA concentrations, but produced a modest potentiation of the effects of 10 mg·kg-1 i.v. AEA [1]. Clinical trial: N/A
    
    Reference:[1] Thors L,Burston JJ,Alter BJ,McKinney MK,Cravatt BF,Ross RA,Pertwee RG,Gereau RW 4th,Wiley JL,Fowler CJ. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br J Pharmacol.2010 Jun;160(3):549-60.
- Properties
  - Categories
    
    Flavonoid isoflavone
    
    Alternative Name
    
    5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
    
    CAS Number
    
    491-80-5
    
    Molecular Formula
    
    C16H12O5
    
    Molecular Weight
    
    284.26
    
    Purity
    
    98.00%
    
    Solubility
    
    insoluble in EtOH; insoluble in H2O; ≥14.21 mg/mL in DMSO
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
    
    * For Research Use Only