Structural features of the reaction of N-pivaloyl-2-piperidone with phenyllithium were elaborated. Two compounds (4) and (5) were obtained and their structures were established by X-ray analysis. C16H23NO2(4): monoclinic, C2/c, a=37,197(7), b=8.479(2), c=9.988(2) A, beta=96.5(3)degree, Z=8; C22H27NO (5): orthorhombic, P2-12-12-1, a=8.244(2), b=10.305(2), c=22.616(5) A, Z=4.
This review summarizes some of the recent findings concerning the long-held tenet that the enzyme, N-acetyltransferase, which is involved in the production of N-acetylserotonin, the immediate precursor of melatonin, may in fact not always control the quantity of melatonin generated. New evidence from several different laboratories indicates that hydroxyindole-O-methyltransferase, which O-methylates N-acetylserotonin to melatonin may be rate-limiting in some cases. Also, the review makes the point that melatonin's actions are uncommonly widespread in organs due to the fact that it works via membrane receptors, nuclear receptors/binding sites and receptor-independent mechanisms, i.e., the direct scavenging of free radicals. Finally, the review briefly summarizes the actions of melatonin and its metabolites in the detoxification of oxygen and nitrogen-based free radicals and related non-radical products. Via these multiple processes, melatonin is capable of influencing the metabolism of every cell in the organism.
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