ISOQUINOLINES Flashcards
ALKALOIDS FROM BENZYLISOQUINOLINES
Morphinan
Aporphine
Bis- Benzyl IQ
Phthalide-THIQ
MAIN ALKALOIDS OF OPIUM
Moprhine Codeine Thebaine Noscapine Papaverine
The alkalods are largely combined insalt form with meconic acid. Opium contains between 3-5% of this organic acid. It is easily detected either in the free-state or as meconate by the formation of a deep redcolour by the addition of ferric chloride. As it is invariably found in opium, its presence is used as a rapid and reasonably specific test for opium
PHYSICOCHEMICAL PROPERTIES OF THE OPIUM ALKALOIDS
Of the main opium alkaloids, morphine displays acidic properties, as
well as the basic properties due to the tertiary amine. Morphine has a
phenanthrene nucleus, and both a phenolic and an alcoholic hydroxyl
group, being acidic due to its phenolic hydroxyl. This acidity can be
exploited for the preferential extraction of these alkaloids (principally
morphine) from an organic solvent by partitioning with alkaline
solution.
Morphine, codeine and thebaine are strong bases, whereas noscapine
and papaverine are weak bases.
PHYSICOCHEMICAL PROPERTIES OF MORPHINE AND CODEINE
MORPHINE
HO- Forms salts with strong bases
NCH3; basic nitrogen: forms soluble salts in acidic water
HO: Hydroxyl group without acidic character
Insoluble in diethyl ether
CODEINE
H3CO - Does not formsalts with strong bases
NCH3; basic nitrogen: forms soluble salts in acidic water
HO: Hydroxyl group without acidic character