d,l-6a-13C-Glaucine 1.5 phosphate
| Autor: | Jerry P. Heeschen, Richard A. Nyquist, Curtis D. Pfeiffer, Daniel R. Henton, Christian T. Goralski |
|---|---|
| Rok vydání: | 1989 |
| Předmět: |
Hydrochloride
Hydrobromide Organic Chemistry Free base Biochemistry Analytical Chemistry chemistry.chemical_compound Sodium borohydride chemistry Drug Discovery Hydroxide Organic chemistry Radiology Nuclear Medicine and imaging Methiodide Phosphoric acid Sodium acetate Spectroscopy Nuclear chemistry |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 27:297-307 |
| ISSN: | 0362-4803 |
| DOI: | 10.1002/jlcr.2580270308 |
| Popis: | d, l-Glaucine 1.5 H3PO4, is a non-narcotic antitussive for which a sample of carbon-13 labelled material was required for metabolism studies in humans. The sample of 99% enriched d, l-6a-13C-glaucine 1.5 H3PO4 was prepared in 7 steps in 36% overall yield starting with purchased 99% enriched 1-13C-papaverine. The papaverine was N-methylated with methyl iodide and the resulting methiodide reduced to d, l-1-13C-laudanosine with sodium borohydride. The laudanosine was O-demethylated with 48% HBr and cyclized to d, l-6a-13C-1,2,9,10-tetrahydroxyaporphine (THA) using aqueous ferric chloride/sodium acetate and isolated as the hydrochloride salt (THA ± HCl). The THA ± HCl was converted to the free base and remethylated with phenyltrimethylammonium hydroxide. The resulting d, l-6a-13C-glaucine was purified by column chromatography and isolated as the hydrobromide salt. The d, l-6a-13C-glaucine 1.5 H3PO4 was obtained by conversion of the hydrobromide to the free base and treatment with 85% phosphoric acid in ethanol. |
| Databáze: | OpenAIRE |
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