Mark A. Philbrick, BYU
Professor Steven Castle, left, joins student Spencer Jones, who has led the way in creating a synthetic compound.

Brigham Young University chemists hope that a synthetic compound they created that is similar to the molecular structure of morphine will have painkilling properties without the drug's addictive quality.

The researchers, led by undergraduate Spencer Jones and advised by Steven Castle, assistant professor of chemistry, created a mirror-image version of a molecule from the Japanese tape vine. That new synthetic molecule is very similar to the molecule for morphine. Now they're making more of the compound so it can be sent to the National Institutes of Health, which will check to see if it does, indeed, have painkilling properties, as they suspect.

Japanese tape vine, or Stephania japonica, from which they derived their Hasubanonine compound, is found in Australia on the outskirts of rain forests. Japanese scientists had already isolated the Hasubanonine molecule from the plant. How the BYU team, in turn, created the synthetic version of the molecule is outlined in the most recent issue of "Organic Letters." Castle, Jones and postdoctoral researcher Liwen He co-wrote the article.

It's unusual for so much of published research to be done by an undergraduate, Castle said, but BYU emphasizes undergraduate mentoring that lets students work closely with professors on research. He called Jones, who is 90 percent or more responsible for the research and will start graduate school at Princeton in September, "exceptional."

A release from BYU quotes Erik Sorensen, the Arthur Allan Patchett Professor in Organic Chemistry at Princeton, on the difficulty involved in such chemical synthesis and synthetic compound creation. They are complex, and it's hard to make them efficiently, he said.

"Steve and his students did beautifully in solving a difficult problem in complex alkaloid synthesis," said Sorensen, in the release. "I am impressed by the logic of their plan for synthesis and the outcomes they achieved."

The molecule made by the vine has no painkilling properties, Castle said, but most naturally produced molecules have mirror images. And the tape-vine's mirror image is close in structure to the morphine molecule. "We've synthesized a mixture of the two mirror-image compounds, the idea being we can take the mirror image of the natural one, send it to NIH to be tested to see if it kills pain. We are optimistic it has painkilling properties, and, if that's true, we are able to synthesize it fairly easily."

It's not well understood what structural features are responsible for the addictive properties of morphine, Castle said. But it is possible they have found a key to a kinder morphinelike drug that would have potential medicinal applications.

Morphine has been used for many years as a painkiller. And though new drugs have come along, it is still widely used. Soldiers, for instance, carry it onto the battlefield. It is also, Castle notes, much harder to synthesize than the compound they've created, so if it does prove to be an effective painkiller, it has some built-in advantages.

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