Biphenylindanone A

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	866823-73-6 ;
PubChem CID	9868580;
IUPHAR/BPS	3954;
ChemSpider	8044271 ;
ChEMBL	ChEMBL593013 ;
CompTox Dashboard (EPA)	DTXSID90432098 ;
Chemical and physical data
Formula	C30H30O4
Molar mass	454.566 g·mol−1
3D model (JSmol)	Interactive image;
	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,[1] 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.[2]

BINA decreases cocaine self-administration in rats, with no effect on food self-administration, and is in regard to this discrimination superior to the mGluR_2/3 agonist LY-379,268.[3]

References

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.
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.
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.

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[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.

[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.

[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.