(R)-3-Nitrobiphenyline

(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 ;
PubChem CID	16757089;
ChemSpider	23288036 ;
ChEMBL	ChEMBL242693 ;
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 ; Key:NMSAVNXFCXMJJY-GFCCVEGCSA-N ;
	(verify)

(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]

References

Crassous PA, Cardinaletti C, Carrieri A, Bruni B, Di Vaira M, Gentili F, Ghelfi F, Giannella M, Paris H, Piergentili A, Quaglia W, Schaak S, Vesprini C, Pigini M (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): 3964–8. doi:10.1021/jm061487a. PMID 17630725.
Del Bello, Fabio; Mattioli, Laura; Ghelfi, Francesca; Giannella, Mario; Piergentili, Alessandro; Quaglia, Wilma; Cardinaletti, Claudia; Perfumi, Marina; Thomas, Russell J.; Zanelli, Ugo; Marchioro, Carla; Dal Cin, Michele; Pigini, Maria (11 November 2010). "Fruitful Adrenergic α2C-Agonism/α2A-Antagonism Combination to Prevent and Contrast Morphine Tolerance and Dependence". Journal of Medicinal Chemistry. 53 (21): 7825–7835. doi:10.1021/jm100977d. PMID 20925410.

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[pmid17630725-1] Crassous PA, Cardinaletti C, Carrieri A, Bruni B, Di Vaira M, Gentili F, Ghelfi F, Giannella M, Paris H, Piergentili A, Quaglia W, Schaak S, Vesprini C, Pigini M (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): 3964–8. doi:10.1021/jm061487a. PMID 17630725.

[2] Del Bello, Fabio; Mattioli, Laura; Ghelfi, Francesca; Giannella, Mario; Piergentili, Alessandro; Quaglia, Wilma; Cardinaletti, Claudia; Perfumi, Marina; Thomas, Russell J.; Zanelli, Ugo; Marchioro, Carla; Dal Cin, Michele; Pigini, Maria (11 November 2010). "Fruitful Adrenergic α2C-Agonism/α2A-Antagonism Combination to Prevent and Contrast Morphine Tolerance and Dependence". Journal of Medicinal Chemistry. 53 (21): 7825–7835. doi:10.1021/jm100977d. PMID 20925410.