アドレナリン及びその類縁化合物の酸分解について (第1報)

Adrenalineの結晶性酸分解産物について

抄録

Epinephrine was boiled in mineral acid and a new substance was formed by its decomposition. In the case of hydrochloric acid, crystals of m.p. 264-265° (decomp.), comparatively sparingly soluble in water, were obtained in approx. 30-40% yield. The yield was lower with other acids. This substance had a molecular weight of 344.5 and corresponded to formula C₁₇H₁₈O₄NCI⋅1/2H₂O. Treatment with acetic anhydride afforded a pentaacetyl compound (I) of m.p. 182-183°, C₂₇H₂₇O₉N; I.R. γ_max^Nujol 6.06μ (-CO-N-). Treatment with dimethyl sulfate gave a pentamethyl compound (II), m.p. 263-264°, C₂₄H₃₃O₈NS, which formed a methiodide (III), m.p. 284-285°, C₂₃H₃₀O₄I on the application of aqueous solution of potassium iodide.
Since the basification of the decomposition mother liquor afforded methylamine, this decomposition reaction may be represented by the following equation: 2 C₉H₁₃ON-CH₃NH₂-2 H₂O=C₁₇H₁₇O₄N A tentative designation of adnamine was given to this substance. Adnamine colors scarlet with alkali hydroxide while the crystals (IV) of m.p. 230-233° (decomp.), obtained by catalytic reduction of its hydrochloride by absorption of 1 mole of hydrogen, does not show any such coloration.