Both mepivacaine and bupivacaine are local anesthetics used in epidural blocks. Mepivacaine has a pKa of 7.6, whereas bupivacaine has a pKa of 8.1. Based on their pKa values, which of these will have more of the uncharged form available at physiological pH, thereby blocking pain quicker?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.4: Substituent Effects On Acidity
Problem 7P: Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a...
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Both mepivacaine and bupivacaine are local anesthetics used in epidural blocks. Mepivacaine has a pKa of 7.6, whereas bupivacaine has a pKa of 8.1. Based on their pKa values, which of these will have more of the uncharged form available at physiological pH, thereby blocking pain quicker?

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