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Biphenylindanone A

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Chemical compound Pharmaceutical compound
Biphenylindanone A
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 3’-(((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro- 1H-inden-5-yl)oxy)methyl)biphenyl-4-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H30O4
Molar mass454.566 g·mol
3D model (JSmol)
SMILES
  • c3cc(C(O)=O)ccc3-c(ccc4)cc4COc(c1C)cc(c(C2=O)c1C)CC2C5CCCC5
InChI
  • 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)
  • Key:KMKBEESNZAPKMP-UHFFFAOYSA-N
  (verify)

Biphenylindanone A (BINA, LS-193,571) is a research agent which acts as a potent and selective positive allosteric modulator for the group II metabotropic glutamate receptor subtype mGluR2.

In animal studies it showed anxiolytic and antipsychotic effects, and blocked the effects produced by the hallucinogenic drug DOB. BINA and other selective mGluR2 positive modulators have therefore been suggested as a novel class of drugs for the treatment of schizophrenia which may have superior properties to traditional antipsychotic drugs.

BINA decreases cocaine self-administration in rats, with no effect on food self-administration, and is in regard to this discrimination superior to the mGluR2/3 agonist LY-379,268.

References

  1. Galici R, Jones CK, Hemstapat K, Nong Y, Echemendia NG, Williams LC, et al. (July 2006). "Biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2, has antipsychotic- and anxiolytic-like effects in mice". The Journal of Pharmacology and Experimental Therapeutics. 318 (1): 173–85. doi:10.1124/jpet.106.102046. PMID 16608916. S2CID 14653620.
  2. Benneyworth MA, Xiang Z, Smith RL, Garcia EE, Conn PJ, Sanders-Bush E (August 2007). "A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis". Molecular Pharmacology. 72 (2): 477–84. doi:10.1124/mol.107.035170. PMID 17526600. S2CID 3097502.
  3. Jin X, Semenova S, Yang L, Ardecky R, Sheffler DJ, Dahl R, et al. (September 2010). "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): 2021–36. doi:10.1038/npp.2010.82. PMC 2922422. PMID 20555310.
Metabotropic glutamate receptor modulators
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators
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