Question

Epinephrine is a hormone secreted by the adrenal medulla. Among its actions, it is a bronchodilator. Albuterol, sold under several trade names, including Proventil and Salbumol, is one of the most effective and widely prescribed antiasthma drugs. The \(R\) enantiomer of albuterol is 68 times more effective in the treatment of asthma than the \(S\) enantiomer. NCC(O)c1ccc(O)c(O)c1 (R)-Epinephrine (R)-Albuterol (Adrenaline) (a) Classify each amine as a primary, secondary, or tertiary. (b) Compare the similarities and differences between their structural formulas.

Short answer

Question: Classify the amines in Epinephrine and Albuterol and briefly describe their structural similarities and differences. Answer: In Epinephrine, there is a primary (1°) amine, while Albuterol contains a secondary (2°) amine. Both compounds have amine groups, hydroxyl groups, and aromatic rings in their structures. Epinephrine has two hydroxyl groups, whereas Albuterol has only one. Additionally, Albuterol has two methyl groups attached to the nitrogen atom of the amine.

Step-by-step solution

Draw the structural formulas of Epinephrine and Albuterol

To classify amines and compare structural formulas, we first need to draw the structures of both Epinephrine and Albuterol. Epinephrine (R-enantiomer): The SMILES code provided corresponds to Epinephrine. Its structure can be drawn as follows: H H \/ H-C-C-NH2 | C || O Albuterol structure (R-enantiomer): O || R-C-N-CH3 | CH3

Identify the amine groups in their structures

Now let's identify the amine groups (nitrogen atom with attached hydrogen and/or carbon atoms) in the structure of Epinephrine and Albuterol. In Epinephrine, we have an amine group (-NH2) attached to a carbon atom. In Albuterol, we have an amine group (-N-) with two carbon atoms and one hydrogen atom attached.

Classify each amine as primary, secondary, or tertiary

To classify amines, we look at the number of carbon atoms attached to the nitrogen atom: - Primary (1°) amine: one carbon atom attached - Secondary (2°) amine: two carbon atoms attached - Tertiary (3°) amine: three carbon atoms attached In Epinephrine, we have a primary (1°) amine (-NH2) because there is only one carbon atom attached to the nitrogen atom. In Albuterol, we have a secondary (2°) amine (-N-) because there are two carbon atoms attached to the nitrogen atom.

Compare their structural formulas for similarities and differences

To compare the structural formulas of Epinephrine and Albuterol, let's look at each part of their structure: 1. Both compounds contain an amine group, which is one of the main functional groups involved in their biological activity. 2. Epinephrine has a primary (1°) amine, whereas Albuterol contains a secondary (2°) amine. 3. Both molecules have hydroxyl groups (-OH) and aromatic rings in their structure. However, Epinephrine has two hydroxyl groups, while Albuterol has only one. 4. Albuterol has alkyl groups attached to the nitrogen atom of the amine- specifically, two methyl groups (-CH3). In conclusion, we've successfully classified the amines in Epinephrine and Albuterol and compared their structural formulas for similarities and differences.

Key concepts

Understanding Organic Chemistry and Amines

Organic chemistry is the scientific study of the structure, properties, and reactions of organic compounds, which are those containing carbon. Amines, which form a key part of this field, are compounds and functional groups that consist of a nitrogen atom attached to one or more alkyl or aryl groups. Learning to identify and classify amines is essential in organic chemistry because they play a significant role in the chemistry of life.

For instance, when classifying amines as primary, secondary, or tertiary, we focus on the number of carbon-containing groups attached to the nitrogen atom. A primary amine has one carbon group attached, a secondary amine has two, and a tertiary amine has three. This distinction is crucial as the structure affects an amine's properties and reactivity.

Improving the learning experience involves breaking down complex structures into understandable components. For example, visual aids to demonstrate the differences between amine classifications could greatly enhance comprehension. Additionally, explaining why certain amines are used in specific medications can provide a practical context to the theory.

Enantiomers in Pharmacology: Their Importance and Impact

Enantiomers are mirror-images of a molecule that cannot be superimposed on one another. This concept is incredibly important in pharmacology because enantiomers of drug compounds often exhibit different biological activities. For example, the 'R' and 'S' designations denote the two enantiomers of a molecule, where 'R' (from the Latin rectus) suggests the right-handed configuration, and 'S' (from the Latin sinister) implies the left-handed one.

Using the case of albuterol, which was discussed in the exercise, the 'R' enantiomer is significantly more effective in treating asthma than the 'S' enantiomer. Understanding these differences can determine the success of a medication and its side effects, as the body can react differently to each enantiomer. When constructing educational material for students, bringing real-life examples, such as albuterol, makes the concept more relatable and underscores the necessity for precise drug design and development. Going beyond the textbooks and into practical implications helps drive home the lessons on enantiomers in medicine.

Comparing Structural Formulas of Organic Molecules

The comparison of structural formulas in organic chemistry is an exercise in understanding how slight variations can lead to significant differences in chemical behavior and physiological effect. Structural formula comparison allows chemists to determine the role of different functional groups, the location of double bonds, or the orientation of atoms in space, among other aspects. In our exercise, identifying the primary amine in epinephrine and the secondary amine in albuterol elucidated their classification.

In providing a step-by-step guide, it's beneficial to offer visual representations of each molecule's structural formula for a direct comparison. This enables students to visually discern the differences and similarities themselves, solidifying their understanding of the material. For instance, pointing out the aromatic rings and the hydroxyl groups' placements in both molecules encourages students to practice critical observation skills. By showing how these structural differences correspond to changes in pharmaceutical effects, educators can bridge the gap between theory and application, which is often a challenging step for learners.