A positive allosteric modulator of mGluR2
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Biphenylindanone A

Item No. 11986

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3'-[[(2-cyclopentyl-2,3-dihydro-6,7-dimethyl-1-oxo-1H-inden-5-yl)oxy]methyl]-[1,1'-biphenyl]-4-carboxylic acid
CAS Number
866823-73-6
Synonyms
  • BINA
  • MRLSD 230
Molecular Formula
C30H30O4
Formula Weight
454.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1.6 mg/mlDMSO: 1.3 mg/mlEthanol: 0.20 mg/ml
λmax
209, 271 nm
SMILES
CC1=C(C)C2=C(CC(C3CCCC3)C2=O)C=C1OCC4=CC(C5=CC=C(C(O)=O)C=C5)=CC=C4
InChi Code
InChI=1S/C30H30O4/c1-18-19(2)28-25(15-26(29(28)31)22-7-3-4-8-22)16-27(18)34-17-20-6-5-9-24(14-20)21-10-12-23(13-11-21)30(32)33/h5-6,9-14,16,22,26H,3-4,7-8,15,17H2,1-2H3,(H,32,33)
InChi Key
KMKBEESNZAPKMP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $117

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    10 mg

    $203

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    25 mg

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    Product Description

    Biphenylindanone A (BINA) is a positive allosteric modulator of mGluR2, stimulating the human and rat receptors with EC50 values of 33.2 and 96 nM, respectively.1 It has no effect on glutamate-induced activation of other mGluR types.1 BINA can be used on cells, tissues, or animals.1,2 Because of its selectivity for mGluR2, robust in vivo activity, and brain penetrance, BINA can be used to elucidate the role of mGluR2 in such diverse processes as psychosis, schizophrenia, and drug addiction.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Galici, R., Jones, C.K., Hemstapat, K., et al. Biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2, has antipsychotic- and anxiolytic-like effects in mice. J. Pharmacol. Exp. Ther. 318(1), 173-185 (2006).

    2. Dhanya, R.P., Sidique, S., Sheffler, D.J., et al. Design and synthesis of an orally active metabotropic glutamate receptor subtype-2 (mGluR2) positive allosteric modulator (PAM) that decreases cocaine self-administration in rats. J. Med. Chem. 54(1), 342-353 (2011).

    3. Benneyworth, M.A., Xiang, Z., Smith, R.L., et al. A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis. Mol. Pharmacol. 72(2), 477-484 (2007).

    4. Hackler, E.A., Byun, N.E., Jones, C.K., et al. Selective potentiation of the metabotropic glutamate receptor subtype 2 blocks phencyclidine-induced hyperlocomotion and brain activation. Neuroscience 168, 209-218 (2010).

    5. Jin, X., Semenova, S., Yang, L., et al. The mGluR2 positive allosteric modulator BINA decreases cocaine self-administration and cue-induced cocaine-seeking and counteracts cocaine-induced enhancement of brain reward function in rats. Neuropsychopharmacology 35(10), 2021-2036 (2010).