IUCr journals

Salvinorin B methoxymethyl ether

Acta Cryst. (2012). E68, o3225-o3226 (http://doi.org/jw3)

[Overlay] The MOM ether of MOM-salB (blue) overlaid on the acetate group of salvinorin A (black) in their respective crystal structures. Overlapping van der Waals radii are shown as translucent spheres. Note how counter-intuitive this overlap appears from the structure diagrams.

MOM-salB is a derivative of the naturally occurring k-opioid salvinorin A, with higher potency and a longer duration of action. In the crystal structure, the MOM ether adopts a 'classic anomeric' conformation. Counter-intuitively, this permits both the terminal oxygen atom and the methyl group to overlap with their counterparts in salvinorin A. This suggests a possible common bioactive conformation. The weaker preference for the classic anomeric conformation in substituted acetals may contribute to the reduced potency of substituted derivatives of MOM-salB.

T. A. Munro, D. M. Ho and B. M. Cohen