Oxidation and degradation products of papaverine. Part I: Gadamer and Schulemann's papaverinol synthesis revisited.
In 1915 Gadamer published in this journal [1] a procedure for the synthesis of papaverinol 2 from papaverine 1 in excellent yield. However, he did not investigate the formation of a violet fluorescence produced upon crystallization of papaverinol 2 from ethanol. The compound responsible for this fluorescence was isolated and identified as the yet unknown quaternary ammonium ion 4, a 6a, 12a-diazadibenzo-[a, g]fluorenylium derivative. The isolation of 4 and its structure determination by spectroscopic methods are described. However, its formation mechanism is unknown.
Hermann
Tadeusz W
TW
Department of Physical Chemistry, K. Marcinkowski University of Medical Sciences, Poznań, Poland. hermann@mail.usoms.poznan.pl
Girreser
Ulrich
U
Michalski
Paweł
P
Piotrowska
Karolina
K
D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D017669:Mercury Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D010208:Papaverine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D017669:Mercury Compounds; C039657:papaverinol; D010208:Papaverine