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Understanding Chiral Compounds: Analyzing Isomers in Common Pharmaceuticals

This guide explores the concept of chirality in various pharmaceutical compounds, including Naproxen, Ibuprofen, Prozac, R-ketamine, Darvon, and Thalidomide. We will analyze the enantiomeric excess and optical purity of these drugs, determining which is the S and R isomer. Through problem-solving, we make distinctions between the isomers based on their activity and effects. Learn to calculate the percentage of each enantiomer and understand the significance of chirality in drug action and safety.

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Understanding Chiral Compounds: Analyzing Isomers in Common Pharmaceuticals

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  1. 4 different groups but 5 bonds bonds to P plane of symmetry theoretically chiral

  2. Problem 1(3.9) Naproxen 97% enantiomeric excess (+/S isomer) or 97% optical purity Which is S isomer? What is the % of S & R in the mix? S-R S+R ee = 97% = (100%)

  3. Ibuprofen (problem 2) S isomer is very active, R is slowly converted to S Which is R, which is S?

  4. Problem 3 prozac - S isomer significantly more active, which is S?

  5. (problem 4) R-ketamine is hallucinogenic S-ketamine anaesthetic Which is R, which is S?

  6. (problem 5) Darvon 2S,3R-propoxyphen analgesic Novrad antitussive - 2R,3S Which is which?

  7. (problem 6) Thalidimide R-sedative, anti-inflammatory, Crohn’s disease S -teratogenic, Assign R and S.

  8. problem 1(3.9) Naproxen 97% enantiomeric excess (+/S isomer) S-R S+R ee = 97% = (100%) S 97% pure,  3% mix (S + R) 3% mix, 1.5%S + 1.5%R 97+1.5%S = 98.5%S, 1.5%R R

  9. Ibuprofen (problem 2) R S S isomer is very active, R is slowly converted to S Which is R, which is S?

  10. Problem 3 R prozac - S isomer significantly more active, which is S? S

  11. R-ketamine is hallucinogenic S-ketamine anaesthetic Which is R, which is S? (problem 4) pull CO forward CH2 to back S 1 2 3 R

  12. (problem 5) Darvon 2S,3R-propoxyphen analgesic Novrad antitussive - 2R,3S Which is which? rotate 4’s to back S R

  13. S R (problem 6) Thalidimide R- sedative, anti-inflammatory, Crohn’s disease S -teratogenic, assign R and S.

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