Phenanthrene alkaloids pharmacology

These domino reactions have also been employed by us for the total synthesis of pharmacologically important [50,51] aporphine alkaloids namely dehydronomuciferine (1) and ( ) N-nomuciferine (2)(Scheme 1), and biologically active [52] phenanthrene alkaloids namely N-noratherosperminine (3) and atherosperminine (4)(Scheme 2). Incidentally, phenanthrene alkaloids are related to the aporphines, from which they can be obtained by degradative procedures [37],... 

Noscapine [128-62-1] (45) is the second most abundant alkaloid found in opium. Unlike most opium alkaloids, however, it has an isoquinoline rather than a phenanthrene ting system. Noscapine was first isolated in 1817 but its antitussive activity was not demonstrated pharmacologically until 1952 (63). Clinical studies have confirmed its effectiveness. It is not a narcotic and has a wide margin of safety when given orally. Death could be produced in rats only with doses > 800 mg/kg (64). Noscapine is isolated from the water-insoluble residue remaining after processing opium for the manufacture of morphine. 

The capsules and stems of Papaver somniferum contain opiate alkaloids essential in medicine. They are classified into two groups, phenanthrene types (morphine, codeine, thebaine) and benzylisoquinoline types [papaverine and noscapine(narcotine)]. These two types of alkaloids show sharply specific pharmacological properties. It is noteworthy that morphinane alkaloids are formed from (-)-(/ )-reticuline, whereas most other alkaloids derive from (-l-)-(5)-re-ticuline 11). 

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