The structure of propranolol hemisuccinate.
1-(N-hemisuccinyl-N-isopropylamino)-3-(1-naphthoxy)-2-propranolol, contaminated with a small amount of the N,O-dihemisuccinyl derivative, is formed when propranolol [1-isopropylamino-3-(1-naphthoxy)-2-propranolol] is allowed to react with succinic anhydride (pyridine, 70 degrees C, 5 hours). This conjugate, used by others for the preparation of an immunogen of propranolol for development of radioimmunoassay methodology for its sensitive quantitation, was previously assigned the O-hemisuccinate structure. The amide structure is assigned on the basis of comparison of infrared and nuclear magnetic resonance spectral data obtained on the product of succinylation of propranolol with data from the model compounds O-acetylpropranolol, N-acetylpropranolol and N,O-diacetylpropranolol.
D000215:Acylation; D055598:Chemical Phenomena; D002621:Chemistry; D004355:Drug Stability; D009682:Magnetic Resonance Spectroscopy; D011433:Propranolol / Q000031:analogs & derivatives*
D011433:Propranolol