Bopindolol

Bopindolol is an ester prodrug of mepindolol. It acts as a non-selective or dual β1- and β2-adrenergic receptor antagonist. Bopindolol has intrinsic sympathomimetic activity (ISA) and membrane-stabilizing activity (MSA). Besides the β1- and β2-adrenergic receptors, bopindolol shows very low affinity for the β3-adrenergic receptor and interacts with certain serotonin receptors such as the serotonin 5-HT1A receptor with strong affinity. ==Chemistry==

The predicted log P of bopindolol ranges from 4.45 to 4.7. It showed the highest predicted lipophilicity of 30clinically relevant beta blockers, with the second most lipophilic beta blocker predicted to be the better-known penbutolol. Synthesis The reaction of 4-Hydroxy-2-methylindole [35320-67-3] (1) with epichlorohydrin in the presence of lye led to 2-methyl-4-(oxiran-2-ylmethoxy)-1H-indole [62119-47-5] (2). Addition of tert-butylamine led to 4-(2-Hydroxy-3-tert-butylaminopropoxy)-2-methylindole [23869-98-9] (3). Ester formation with benzoic anhydride [93-97-0] (4) in the presence of hexamethylphosphoric acid triamide [680-31-9] completed the synthesis of Bopindolol (5). File:Bopindolol synthesis.svg|thumb|center|500px|Thieme Patent: Starting amnine: ==History==

Bopindolol is related to and was developed as a successor to pindolol. It was first described in the literature by at least 1977. ==References==