Researches on morphine. Pt. 1 / by S.B. Schryver and and Frederic H. Lees.

  • Samuel Barnett Schryver
Date:
[1900]
Catalogue details

Licence: In copyright

Credit: Researches on morphine. Pt. 1 / by S.B. Schryver and and Frederic H. Lees. Source: Wellcome Collection.

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    Knorr represents the reactions by the following formulae : OMev. n ^0*CH OH^iAoMMe Codeine. !>ch2 — OMe OH >C14H10< o CHc '14—10 ^NMe(Me-OH) Codeine methohydroxide. >CH„ - °“H>C14H9-0-CH2-CH2-NMe2 Methylmorphimethine. — °OH>CnH3 + OH-OH2-CH2-NMe2 . Hydroxymethoxyphenanthrene. Dimethyloxethylamine. The synthetical base, naphthalanmorpholine, undergoes similar transformations : C10Hw<.O^i>OH2 — C10H9-O-CH2-CH2-NMe2 -> C10H8 + OH*CH2-CH2-NMe2 (Ber., 1889, 22, 181, 1113, 2081 ; 1894, 27, 1149 ; 1899, 32, 737, 742 ; Annalen, 1898, 301, 1 ; 1899, 307, 171). Vongerichten’s more recent researches deal principally with the nitrogen-free decomposition products of morphine (Ber., 1897, 30, 355, 2441 ; 1898, 31, 51, 3198; 1899, 32, 1521, 2379; 1900, 33, 352). He shows that the /Tmethylmorphimethine discovered by Knorr (Ber., 1894, 27, 1149) is not acted on by acetic anhydride, but that its methiodide on treatment with alkalis readily decomposes, giving as a main product a monohydroxyphenol, C14H802 (morphenol), which readily reduces to the dihydroxyphenanthrene (morphol), of which the methyl ether was obtained by Knorr, as just described. As a result of his researches, Vongerichten assigns the two following formulae to mor¬ phenol and morphol respectively : Morphenol. Morphol. These formulae become of special interest in view of the recent researches of Pschorr and his collaborators on the synthesis of the hydroxyphenanthrenes, and from the results we can obtain some clue to the positions which the hydroxyl groups and the morpholine residue