Question

A codeine-containing cough syrup lists codeine sulfate as a major ingredient instead of codeine. The Merck Index gives \(\mathrm{C}_{36} \mathrm{H}_{44} \mathrm{N}_{2} \mathrm{O}_{10} \mathrm{S}\) as the formula for codeine sulfate. Describe the composition of codeine sulfate. (See Exercise \(155 .\) ) Why is codeine sulfate used instead of codeine?

Short answer

Codeine sulfate, with the molecular formula \(\mathrm{C}_{36} \mathrm{H}_{44} \mathrm{N}_{2} \mathrm{O}_{10} \mathrm{S}\), is an organic compound composed of 36 carbon atoms, 44 hydrogen atoms, 2 nitrogen atoms, 10 oxygen atoms, and 1 sulfur atom. It is used instead of codeine due to its better water solubility, increased stability, and slower metabolism rate, resulting in improved efficacy, longer shelf life, and a more controlled release of the active component. These properties make codeine sulfate a preferred choice for medical applications such as cough syrups.

Step-by-step solution

Break down the molecular formula

The molecular formula of codeine sulfate is given as \(\mathrm{C}_{36} \mathrm{H}_{44} \mathrm{N}_{2} \mathrm{O}_{10} \mathrm{S}\). This means codeine sulfate is composed of 36 carbon atoms, 44 hydrogen atoms, 2 nitrogen atoms, 10 oxygen atoms, and 1 sulfur atom.

Describe the composition of codeine sulfate

Based on the molecular formula, codeine sulfate is an organic compound as it includes carbon, hydrogen, and nitrogen atoms. The presence of oxygen and sulfur further contributes to the overall structure and properties of the compound. Since it is derived from codeine, it likely has similar pharmacological properties while differing in specific characteristics.

Explain the benefits of using codeine sulfate instead of codeine

Codeine sulfate is used instead of codeine for several reasons: 1. Solubility: Codeine sulfate has better water solubility than codeine. This leads to improved dissolution and absorption in the body, making it more effective. Codeine sulfate's higher solubility makes it convenient for liquid formulations (like cough syrup) to deliver the desired effects. 2. Stability: Codeine sulfate is more stable than codeine under various environmental conditions such as different temperatures and pH levels. This enhanced stability enables longer shelf life and maintains its potency over time. 3. Metabolism: Codeine sulfate is usually metabolized slower by the liver than codeine, leading to a more controlled release of the active component. This results in fewer fluctuations in drug concentration in the bloodstream, allowing for a smoother and sustained therapeutic response. In summary, codeine sulfate is used instead of codeine primarily due to its increased solubility, stability, and metabolism factors, making it a preferred choice for specific medical applications such as cough syrups.

Key concepts

The Chemistry Behind Organic Compounds

Exploring the world of organic chemistry can be fascinating, and codeine sulfate is an interesting example to look at. An organic compound is typically characterized by the presence of carbon atoms bonded to hydrogen atoms, often along with other elements such as oxygen, nitrogen, and sulfur. These compounds form the basis of all life on Earth and are central to biological processes. In the case of codeine sulfate, the compound includes a backbone of carbon atoms along with hydrogen, nitrogen, oxygen, and sulfur atoms.

Understanding organic compounds requires us to look at their molecular structure, which reveals how the atoms are connected to form the compound. Codeine sulfate's molecular structure indicates a complex arrangement that dictates its properties and reactivity. The sulfur atom, in particular, influences the solubility and stability of the compound, making it different from the codeine from which it is derived. This is key to its effectiveness in medicinal applications.

Decoding the Molecular Formula

A molecular formula provides an important snapshot of a chemical substance, detailing the types and quantities of atoms within a compound. For students navigating exercises like the composition of codeine sulfate, dissecting the molecular formula is crucial. Codeine sulfate's formula, \(\mathrm{C}_{36} \mathrm{H}_{44} \mathrm{N}_{2} \mathrm{O}_{10} \mathrm{S}\), tells us the exact number of each atom type present.

Each letter represents a different element on the periodic table, with carbon \(C\), hydrogen \(H\), nitrogen \(N\), oxygen \(O\), and sulfur \(S\). The subscript numbers following these letters tell us how many of each atom the compound contains. For educational clarity, it's beneficial to convey not just the 'what' but also the 'why'. Understanding the atomic composition helps in predicting the physical and chemical properties of the compound, such as its reactivity, phase of matter at room temperature, and interaction with other substances. Codeine sulfate's formula suggests a large, complex structure, which gives insight into its robust therapeutic potential.

Therapeutic Properties of Codeine Sulfate

When it comes to understanding drug compounds, the therapeutic properties are where chemistry meets biology. Codeine sulfate's role in medicine is tied directly to its chemical structure, which influences how it interacts with human physiology. Its therapeutic effects are largely due to its analgesic properties, meaning it can relieve pain. Additionally, codeine sulfate is known for its effectiveness in suppressing cough, rooting its use in cough syrups.

One of the key benefits of codeine sulfate over codeine is its solubility. The sulfate group on the compound makes it more dissolvable in water, which is essential for its uptake and absorption in the body. This means that when a patient takes codeine sulfate orally, in the form of cough syrup for example, the body can absorb and transport it more efficiently to the site where it is needed. Moreover, its controlled metabolism rate minimizes potential for sharp increases or decreases in drug levels, which can lead to side effects or reduced effectiveness. Understanding these properties not only helps in recognizing why codeine sulfate is chosen over codeine but also emphasizes the importance of chemistry in developing effective medications.