(R)-3-Nitrobiphenyline

(R)-3-Nitrobiphenyline is a drug which acts as an α₂-adrenergic agonist, selective for the α_2C subtype, as well as being a weak antagonist at the α_2A and α_2B subtypes. It has been used in scientific research to characterize the binding and functional properties of the α_2C subtype.^[1][2]

(R)-3-Nitrobiphenyline

Clinical data
MedlinePlus	a682611
Identifiers
IUPAC name (R)-2-[1-(3'-Nitrobiphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole
CAS Number	945618-95-1 Y
PubChem CID	16757089
ChemSpider	23288036 Y
ChEMBL	ChEMBL242693 Y
CompTox Dashboard (EPA)	DTXSID401028500
Chemical and physical data
Formula	C17H17N3O3
Molar mass	311.341 g·mol−1
3D model (JSmol)	Interactive image
SMILES c2ccc([N](=O)=O)cc2-c1ccccc1OC(C)C3=NCCN3
InChI InChI=1S/C17H17N3O3/c1-12(17-18-9-10-19-17)23-16-8-3-2-7-15(16)13-5-4-6-14(11-13)20(21)22/h2-8,11-12H,9-10H2,1H3,(H,18,19)/t12-/m1/s1 Y Key:NMSAVNXFCXMJJY-GFCCVEGCSA-N Y
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References

1. Crassous PA, Cardinaletti C, Carrieri A, Bruni B, Di Vaira M, Gentili F, et al. (August 2007). "Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist". Journal of Medicinal Chemistry. 50 (16): 3964–3968. doi:10.1021/jm061487a. PMID 17630725.
2. Del Bello F, Mattioli L, Ghelfi F, Giannella M, Piergentili A, Quaglia W, et al. (November 2010). "Fruitful adrenergic α(2C)-agonism/α(2A)-antagonism combination to prevent and contrast morphine tolerance and dependence". Journal of Medicinal Chemistry. 53 (21): 7825–7835. doi:10.1021/jm100977d. PMID 20925410.