An investigation of the N-demethylation of 3-deoxymorphine and the affinity of the alkylation products to μ, δ, and κ receptors Original Research Article

The N-demethylation of 3-deoxymorphine (1) was investigated using methyl chloroformate and hydrazine. 3-Deoxynormorphine (2) was obtained in 70% yield, and 3-deoxydihydronormorphine (3) was also obtained as a side product. The μ, δ, and κ receptor binding affinity of a series of N-substituted 3-deoxynormorphines 6 and 7 and N-substituted 3-deoxydihydronormorphines 8–11 was also determined.