Metabolism of azulene in rats.
1. Azulene was rapidly metabolized in the rat and excreted in the urine as the sulphate conjugate of 1-hydroxyazulene; 45% of the dose was recovered as pure metabolite from the 0-24 h urine. 2. [1,3(-2)H2]Azulene was converted in vivo to 1-hydroxyazulene sulphate which was shown by 1H-n.m.r. spectroscopy to contain one deuterium at C-3 and essentially no detectable deuterium at C-2. This result suggests that, if a 1,2-oxide of azulene was an intermediate in the 1-hydroxylation, it rearranged with direct loss of deuterium from C-1 rather than an NIH shift to C-2.
D000818:Animals; D052176:Azulenes; D001711:Biotransformation; D003508:Cycloheptanes / Q000378:metabolism*; D006868:Hydrolysis; D006900:Hydroxylation; D066298:In Vitro Techniques; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains
D052176:Azulenes; D003508:Cycloheptanes; C005525:azulene