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Synthesis of Hydroxytripelennamine via O-Demethylation of Pyrilamine

机译：吡咯胺O-去甲基化合成羟基三苯胺

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Tripelennamine (Compound 1, Blues) has been an important antihistamine drug for a long time. Recently, the abuse of pentazocine (Talwin/Ts) in combination with Compound 1 (Ts and Blues) by intravenous narcotic users has been observed in the United States. Although such abuse of pentazocine has now been largely eliminated by the introduction of Talwin NX, the apparent potentiation by Compound 1 of the high from pentazocine reported by narcotic abusers has raised questions concerning this effect. Jasinski and his coworkers report that Compound 1 induced euphoria and is identified as an opiate in humans. It was reported that pentazocine and morphine antinociception was potentiated by Compound 1 in mice and a rat. Several investigations of this potentiation have been undertaken, including the design of experiments to quantify the metabolites of Compound 1. We report the synthesis of one such metabolite, hydroxytripelennamine (Compound 2), and the course of the reactions employed in an unsuccessful attempt of synthesis of Compound 2. O-Demethylation of pyrilamine with 1-propanethiol and potassium tert-butoxide gave hydroxytripelennamine, Compound 2, one of the major metabolites of tripelennamine. The reaction of pyrilamine with other demethylating agents such as 48% of Hydrogen Bromide, Boron Bromide, and Trimethislyl iodide has been explored, and the products thus formed have been isolated and characterized. (AW)

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