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By R.H.F Manske, H.L. Holmes

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Arthur, J . Chern. Soc. p . 2285 (1965). 3. Tomita, M. Kozuka. E. Sakagawa, and Y. Mitsunori, J . Phnrm. Soc. J a p a n 83, 763 (1963). 4. 8. K. Saha, Sci. Cult. (Crtlcuttn) 24, 572 (1959); c'hem. Abstr. 54, 1580 (1960). 5. A. Chatterjee, P. L. Majumdar, R'. Mukherjee, S. K. Saha, and S. K. Talapatra, Tetruhedron Letters p. 1539 (1965). 6 . J. Slavik and L. Slavikova, Collection Czech. Chem. Cornmun. 28, 1720 (1963); Chem. Abstr. 59, 11886 (1963). 7. J. Slavik, Collection Czech. Chem. Cornmun. 30, 914 (1965).

I 7 0 (1966). 52. A. H. Jackson ancl J. A. Martin, Chem. Conamun. S o . 8, p. 142 (1965). 53. BI. Shamma and W. A. n. C o m m u n . KO. 21, p. 528 (1965). 54. W. A. Ayer and W. I. Taylor, J . Chem. Soc. p. 452 (1956). 56. T. Kitamura, J . l'harm. Soc. J a p a n S O , 219 (1960); C'henl. Abstr. 54, 13162 (1960). 56. BI. Tomita and K . Fukagama, J . Pharm. Soc. n. Abslr. 59, 5211 (1963). 57. J . Kunitomo arid M. Kaniiinura, J . Soc. J a p o ) ~82, 1652 (1962). 68. AT. Tomita and T. Ibuka, J . Phorm.

D. N-METHYLCORYDINIUM CATION The N-methylcorydinium cation was obtained from an extract of the bark ofPagara nigrescens Fries, and was first crystallized as the styphnate salt, (mp 206°-2070; [a]: + 129" in acetone). Two other crystalline salts were prepared, the picrate (mp 186"-187"), and the iodide which decomposed gradually between 190" and 200" ([a]? +154' in 50% ethanol-water). Analyses of the styphnate and picrate indicated the formula C21H2,$04@ for the cation. A strong bathochromic shift of the maxima in alkaline solution showed the presence o f a phenolic hydroxyl group, while the elemental analyses also required the presence of three methoxyls.

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