Reduction of norfluorocurarine by sodium in EtOH formed deoxytetrahydronorfluorocurarine and tetrahydronorfluorocurarine. The latter was identical to the Wieland-Humlich 18-deoxyglycol. Reduction of norfluorocurarine by sodium borohydride in alkaline solution occurred with opening of rings C and E and formation of the new indole base 16-decarbmethoxyepistemmadenine. Reduction of fluorocurarine chloride or iodide by sodium borohydride formed the corresponding de-acetylretuline salts. The structures of the products were established by x-ray crystal structure analyses. Norfluorocurarine and representatives of the alpha-methylenindolenine series formed indoline derivatives upon reduction in acidic and neutral solutions; indole derivatives, in alkaline solution.