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Such a subtle property has such a large impact. One thing that has stuck with me since undergraduate chemistry is that if you take the aspirin molecule and flip its chirality what you end up with is toxic and nothing like aspirin! I miss organic chemistry.


Ummm.... aspirin has no chirality. Salicylic acid is planar and the acetyl group can freely rotate.

The best example of chirality and toxicity is thalidomide. One isomer has low toxicity and the other causes horrible birth defects. Unfortunately the two isomers can interconvert so it isn't possible to create a pure sample of just one of them.


"it isn't possible to create a pure sample of just one of them."

Oh, to create a pure sample is a trivial task. But unfortunately it racemizes in your body.

It is actually a very interesting compound. Would not be surprised about a come-back.


Sorry, poor wording on my part. You are correct. You can create a pure sample, but it doesn't stay pure in your body.


You do realise that what you have written makes no sense. How could it be possible to determine that one isomer has low toxicity unless it is possible to separate them?

I am not 100% up to date in this area, but the last time I looked into the isomer theory of thalidomide toxicity it was not well supported by the experimental evidence.




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