And actually, the tests PROVED that thalidomide was perfectly safe. Which the VERSION BEING TESTED was.
When they manufactured thalidomide for testing purposes, they got pure L-thalidomide. Which is safe. When they scaled up, the process made 50/50 L- and R-thalidomide (which are chemically identical). It was the R-thalidomide that did the damage.
So if you gave me a "bottle of thalidomide, perfectly safe for pregnant women" it's quite possible you're telling the truth ...
Posted Feb 9, 2012 22:46 UTC (Thu) by Cyberax (✭ supporter ✭, #52523)
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No, thalidomide is racemic - it spontaneously flips between L- and R- forms.
However, it's a great and simple example of reasons beyond the extensive drug testing which begins with the toxicity tests, and with the compound which will later be certified and sold.
Most patents are drag on the innovation
Posted Feb 10, 2012 13:23 UTC (Fri) by Wol (guest, #4433)
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Exept that's not what "racemic" means. All racemic means is "50/50 L and R", not "L and R spontaneously flip". Actually, that flip is pretty much impossible without something there to catalyse the reaction.
But it's normal to get a pure L or R isomer or a racemic mix, depending how you produce it. And it's quite likely, similar to what you assert, that when they produced commercial quantities one of the production steps contained a catalyst that converted from "all L" to "racemic mix". Which they wouldn't have picked up unless they were actively looking for it.
Cheers,
Wol
Most patents are drag on the innovation
Posted Feb 10, 2012 13:41 UTC (Fri) by Cyberax (✭ supporter ✭, #52523)
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>Exept that's not what "racemic" means. All racemic means is "50/50 L and R", not "L and R spontaneously flip". Actually, that flip is pretty much impossible without something there to catalyse the reaction.
Posted Feb 13, 2012 11:54 UTC (Mon) by nye (guest, #51576)
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>Exept that's not what "racemic" means. All racemic means is "50/50 L and R", not "L and R spontaneously flip". Actually, that flip is pretty much impossible without something there to catalyse the reaction.
I think it's quite common for enantiomers to flip. For example, get some fresh caraway, and note that it smells *very slightly* like spearmint. Then leave it in a jar for a year or two, and note that it now smells rather *strongly* of spearmint as some of the s-carvone has become r-carvone.
Most patents are drag on the innovation
Posted Feb 13, 2012 11:55 UTC (Mon) by nye (guest, #51576)
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And now I notice somebody else has posted the same link. That's what I get for not refreshing the page after the weekend.