Transformation of thebaine to oripavine, codeine, and morphine by rat liver, kidney, and brain microsomes.

Abstract:

:Thebaine, an intermediate of morphine biosynthesis in the poppy plant, Papaver somniferum, was transformed to oripavine, codeine, and morphine by rat liver, kidney, and brain microsomes in the presence of an NADPH-generating system. The formation of morphine, codeine, and oripavine was identified by a specific RIA, HPLC, and GCMS. Thebaine also gave rise to four other compounds, which for the moment are unidentified. NADH dramatically increased the formation of both codeine and morphine when used together with an NADPH-generating system, especially in liver microsomes. NADPH is essential in the formation of oripavine from thebaine and morphine from codeine, while NADH is critical in the conversion of thebaine to codeine and from oripavine to morphine. Carbon monoxide or SKF 525A inhibited the conversion, indicating a role of cytochrome P-450. These results provide evidence for the enzymatic in vitro conversion by mammalian tissues of thebaine to morphine. The pathway is similar to that which exists in plants.

authors

Kodaira H,Spector S

doi

10.1073/pnas.85.4.1267

subject

Has Abstract

pub_date

1988-02-01 00:00:00

pages

1267-71

issue

4

eissn

0027-8424

issn

1091-6490

journal_volume

85

pub_type

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