title: Effect of fluorine substitution on the agonist specificity of norepinephrine.
abstract: Substitution of fluorine for hydrogen in position 2, 5, or 6 of the aromatic ring of norepinephrine markedly alters the alpha- and beta-adrenergic agonist properties of norephinephrine. The 6-fluoro isomer is an beta-adrenergic agonist with virtually no beta agonist activity, while the 2-fluoro isomer is a beta-adrenergic agonist with little alpha activity. The 5-fluoro isomer is equipotent with norepinephrine as an alpha agonist and significantly more potent as a beta agonist. The possible physiochemical basis for these differences is discussed.
mesh_terms: D000818:Animals; D001011:Aorta; D005461:Fluorine; D006168:Guinea Pigs; D006860:Hydrogen Bonding; D066298:In Vitro Techniques; D009638:Norepinephrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011941:Receptors, Adrenergic / Q000187:drug effects*; D011942:Receptors, Adrenergic, alpha / Q000187:drug effects*; D011943:Receptors, Adrenergic, beta / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D011941:Receptors, Adrenergic; D011942:Receptors, Adrenergic, alpha; D011943:Receptors, Adrenergic, beta; D005461:Fluorine; D009638:Norepinephrine