Opium and its alkaloids

American Journal of Pharmaceutical Education,  Summer 2002  by Schiff, Paul L Jr

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BIOSYNTHESIS

The biosynthesis of the various opium alkaloids discussed in this paper has been well researched over the last twenty years and is now firmly established. The precursor (parent) amino acid to all of these alkaloids is L-tyrosine. Oxidative deamination of L-tyrosine followed by decarboxylation affords 4hydroxyphenylacetaldehyde, while decarboxylation of L-tyrosine yields tyramine which is subsequently oxidized to dopamine. Condensation of dopamine and 4-hydroxyphenylacetaldehyde in a Mannich-like fashion yields (S)-norcoclaurine which on methylation is converted to (S)-coclaurine. (S)Coclaurine serves as the key precursor to the benzylisoquinoline papaverine, the phthalideisoquinoline noscapine, and the morphinans morphine, codeine, and thebaine(10).

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