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Identification and synthesis of O-methylcatechol metabolites of phenobarbital and some N-alkyl derivatives

✍ Scribed by Anthony M. Treston; Athena Philippides; Noel W. Jacobsen; Mervyn J. Eadie; Wayne D. Hooper

Publisher: John Wiley and Sons
Year: 1987
Tongue: English
Weight: 565 KB
Volume: 76
Category: Article
ISSN: 0022-3549
DOI: 10.1002/jps.2600760617

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✦ Synopsis

5-Ethyl-5-(4-hydroxy-3-methoxyphenyl) barbituric acid was identified as a new, minor metabolite of phenobarbital in man. The identity of this O-methylcatechol metabolite was confirmed by an unequivocal chemical synthesis, and by GC-MS studies. Mephobarbital and the 1,3-dimethyl, 1-ethyl, and 1,3-diethyl analogues of phenobarbital yielded the corresponding N-alkylated O-methylcatechol metabolites, all of which were confirmed by synthesis. The N-alkyl barbiturates each gave additionally at least one O-methylcatechol metabolite in which N-dealkylation had occurred. These metabolites accounted for approximately 1-5% of the orally administered dose in man.

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