Friday, April 27, 2012

Ready to Make Ketamine ...

I looked at the synthesis route for producing ketamine and I realized, I've learned all of the reactions in Chemistry 345 class! So I decided to figure out and write all the mechanisms as an exam review practice. I'm nerdying out everyday.

Starting with 2-chlorobenzonitrile, it takes just 5 simple reactions to make a ketamine.
1) Grignard reagent with an acidic work-up
2) Carbonyl alpha-bromination via enolate
3) Hydrolysis of tertiary bromide via Sn1
4) Imine formation (happens simultaneously with reaction 3)
5) Ring expansion via alpha-ketol rearrangement
Wow, I didn't know my chemistry knowledge is enough to make a well-known drug now! I'm feeling proud.

Ketamine was first synthesized in 1962 as a substitute for PCP (Angel Dust). She was indeed proven to at least a bit more emotionally stable than her cousin and became an important medicine.
Once Ketamine was commonly sold as Ecstasy at dance clubs, although it makes absolutely no sense to confuse those two drugs with the exactly opposite effects.


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