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Freebasing Lab.doc - Connor Kaniewski September 20th 2016...

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Connor Kaniewski September 20 th , 2016 Medicinal Chemistry Mr. Choi – F Block Freebasing Lab – A lesson in acid/base solubility (55pts) We have learned that a freebase is an uncharged (unionized or non-polar) molecule that does not readily dissolve in water, whereas the acid salt does because it is charged and thus, polar. The strong intermolecular bonds (attractive forces) between polar molecules prevent the acid salt form from vaporizing. The much weaker attractive forces between nonpolar molecules allows the freebase form to readily vaporize. A base can also be seen as a molecule that readily accepts a proton (H+) according to the Bronsted Lowry definition. The freebase form of cocaine (and crack, a less pure form of the free base) takes on a solid form (“rock”) that allows users to smoke it. Smoking cocaine results in users feeling its high faster and stronger when compared to powered cocaine. Free base cocaine is also ideal for being inhaled because of its high lipid solubility (as a free base). It is absorbed almost instantaneously through the alveolar epithelium of the lungs and into oxygenated blood, which is delivered directly to the brain. Snorted cocaine is absorbed by mucus membrane, which takes a more circuitous route to the brain because it travels to deoxygenated blood. Remember your circulatory pathways! In addition, snorted cocaine constricts the blood vessels, resulting in slower delivery of the drug to site of action. The fast and intense high produced by free base cocaine put users at a higher risk for addiction and overdose. The medicinal chemist’s goal is to produce the acid salt of a free base drug because of the increased solubility in water, which is a major component of blood. The chemical definition of a salt is a molecule composed of ions (as compared to a free base that is unionized). Specifically, an acid salt ionizes in water to produce hydronium (H3O+) or H + for short. Cocaine and other medications (many that you may find in your medicine cabinet) mixed with HCl will ionize, making them more water soluble and more stable. Free bases, besides being less water soluble, and thus a poorer form of delivery to the gastrointestinal tract of a patient, do not always crystallize to form a solid but instead turns into an oil. For a pharmacist, a drug in this form would be difficult to administer in accurate doses. In our experiment, we will look at the acid/base properties of different organic molecules. The functional groups of these molecules make that them acid/bases, proton acceptors/ proton donors. We will also use diphenhydramine, a commonly used antihistamine/sedative as a model for producing and extracting a free base drug with fairly high purity. We are using diphenhydramine to MIMIC cocaine but not ACTUALLY WORKING WITH COCAINE .
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