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Phenobarbitol and Human Acid-Base Chemistry

Prof. Sally Boudinot

6. Identifying if a Drug is an Acid or a Base

A first key to understanding pharmaceutics forces us to look once again at the representation of molecules.  We do not need a structure to guide us here, we can simply look at the name of the material.  Many drugs are acids or bases.  A common question is this one: How do we determine if a drug (or any other compound) is an acid or a base? Here are some hints that may help you decide. 

Concept:

Naming molecules so that chemists can determine the structure at the molecular level, unequivocally, is a difficult and patient task.  The chemical world includes nomenclature experts whose task is to develop the systems for accurate naming of chemical compounds for the International Union of Pure and Appied Chemistry.

Let's name some acids: hydrochloric, nitric, sulfuric, acetic, boric, benzoic come to mind. Salts formed by a reaction with these compounds are conjugate acids, so the compound that reacted with them must have been a base, right? Let's name some CONJUGATE ACIDS of basic drugs:
 

Base Salt/Conjugate Acid
Diphenhydramine Diphenhydramine HCL
Glucosamine Glucosamine sulfate
Epinephrine Epinephrine sulfate
Ephedrine Ephedrine HCl
Atropine Atropine sulfate
Tetracycline Tetracycline HCl

Most of these drugs, as you can tell by their name, are "amines", which means they are weak bases. So, diphenhydramine is a base, and diphenhydramine HCl is its conjugate acid.

How about common bases? Some that come to mind include sodium hydroxide, calcium hydroxide, and potassium hydroxide. Salts that result from reactions with these agents are conjugate bases, so the component present in the initial reaction MUST have been an acid! So we see the following examples of conjugate bases of ACIDIC drugs:
 

Acid Salt/Conjugate Base
Phenobarbital Sodium Phenobarbital
Naproxyn Sodium Naproxyn
Fenoprofen Fenoprofen Calcium 
Penicillin G Penicillin G Potassium

If you don't have any idea based on the clues given in the name of the compound, try looking at the salt to see if it is an acid or a base.

 

ChemCases.Com is an NSF supported curriculum project.  The principles of General Chemistry can be linked to the responsible decision making that scientists and others make in the development and use of successful products.  This case is one of a series developed at Kennesaw State University.  Please see a full description of the program at ChemCases.Com

 

Concept Map for this ChemCase

Case Study in Phenobarbitol
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Prof. Sally Boudinot
College of Pharmacy
University of Georgia
Athens, GA
sallyb@rx.uga.edu