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Extra info for A textbook of inorganic chemistry vol.XI part I Organometalic compounds. Derivatives of the elements of groups I to IV
8 elaborated to the "oripavine" range of analgesics and antagonists but is also capable of transformation into codeine and morphine. Clearly, the value of codeine and morphine as analgesics and the large demand for them requires a steady source of supply that, preferably, does not rely on supplies of opium. Papaver bracteatum(61-64) produces thebaine, but not morphine, as its major alkaloid in roots and dried latex and thus is a potential source of codeine. In addition, perhaps, the Rice(36) synthesis of morphine will offer a practical manufacturing process to therapeutic analgesics.
Oxetane isomeric with 116. 003 mg/kg). Reaction of 108 with a single mole of tosyl chloride in pyridine afforded, as well as113, an epimeric mixture of monotosylates (119). The 7 ex. -tosylmethylepimer may be converted with base to the spirooxetane (120). 17. 04 ~mol/kg. 57 (about 4 x morphine). , 129) afforded good agonists, but once again no opioid antagonist actions could be demonstrated. Thus, in series 127 and 125 with 7f3-aralkyl substituents and alkyl chain lengths of two to four methylene units strong opioid agonists were obtained.
17. None of this series had a demonstrable opioid antagonist action; however, they were potent agonists (MW). 005 mol/kg (cf. 003 mol/kg. Generally, the 6-ketones tend to be more potent (two times) analgesics than the 6p-ols, whether in the dihydrocodeinone or dihydromorphinone series. The observation made by the same authors for corresponding morphinans(214-216) (p. 121) applies to the 4,5-epoxy ring-closed species. 5-Epoxymorphinans 108 (R = H) 1 TsCl/Py , ,CH 2OTs CH 20Ts , ,CH 2OTs +-- CH 20H MeO OH 117 113 1 <1!