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B8688

Sigma-Aldrich

Biphenyl-indanone A

≥98% (HPLC), powder

Synonym(s):

3′-[[(2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]methyl]biphenyl-4-carboxylic acid, BINA, Biphenylindanone A

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About This Item

Empirical Formula (Hill Notation):
C30H30O4
CAS Number:
866823-73-6
Molecular Weight:
454.56
MDL number:
MFCD19440914
UNSPSC Code:
12352200
PubChem Substance ID:
329773139

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥18 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

2-8°C

SMILES string

Cc1c(C)c2C(=O)C(Cc2cc1OCc3cccc(c3)-c4ccc(cc4)C(O)=O)C5CCCC5

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

Biochem/physiol Actions

Biphenyl-indanone A (BINA) is a potent selective positive allosteric modulator for the group II metabotropic glutamate receptor subtype mGluR2. In animal studies BINA showed anxiolytic and antipsychotic effects, and blocked the effects produced by the hallucinogenic drug DOB. It decreased cocaine self-administration in rats, with no effect on food self-administration. In recombinant systems, BINA selectively potentiated the response of mGluR2 to glutamate with no effect on the glutamate response of other mGluR receptor subtypes tested.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (G Protein Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

B8688-BULK:
B8688-5MG:
B8688-VAR:
B8688-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jun-Tao Gao et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 43(13), 2615-2626 (2018-10-05)
Opioid abuse is a rapidly growing public health crisis in the USA. Despite extensive research in the past decades, little is known about the etiology of opioid addiction or the neurobiological risk factors that increase vulnerability to opioid use and
Thor C Møller et al.
Scientific reports, 8(1), 10414-10414 (2018-07-12)
G protein coupled receptors (GPCRs) play essential roles in intercellular communication. Although reported two decades ago, the assembly of GPCRs into dimer and larger oligomers in their native environment is still a matter of intense debate. Here, using number and
Guendalina Olivero et al.
British journal of pharmacology, 174(24), 4785-4796 (2017-10-03)
We recently proposed the existence of mGlu We studied the effect of LY566332, an mGlu Cortical synaptosomes possess LY566332-sensitive autoreceptors that are slightly, although significantly, susceptible to LY2389575. In contrast, LY566332-insensitive and LY2389575-sensitive autoreceptors are present in spinal cord terminals.
Maarten L J Doornbos et al.
Biochemical pharmacology, 155, 356-365 (2018-07-22)
While many orthosteric ligands have been developed for the mGlu2 receptor, little is known about their target binding kinetics and how these relate to those of the endogenous agonist glutamate. Here, the kinetic rate constants, i.e. kon and koff, of

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