Photochemical N-demethylation of alkaloids.
Certain alkaloids were observed to undergo N-demethylation processes under photochemical conditions. Tropine, acetyltropine, tropinone, and atropine were cleanly N-demethylated upon treatment with tetraphenylporphin, oxygen, and light. Dextromethorphan also underwent a N-demethylation reaction, but reacted further to afford an imine. In contrast, 14-acyloxycodeinones underwent a photochemically induced tandem N-demethylation acyl migration.
School of Biological and Chemical Sciences, Deakin University, Geelong, Victoria, Australia.
J A
JA
Ripper
E R
ER
Tiekink
P J
PJ
Scammells
D000470:Alkaloids / Q000737:chemistry / Q000378:metabolism*; D003640:Dealkylation; D010777:Photochemistry
D000470:Alkaloids