Experiment # 45: Benzocaine
Abstract
The local anesthetic, benzocaine, was synthesized via the esterification of p-aminobenzoic acid with ethanol. The percent yield of crude product was determined to be 21% and the melting point was recorded at 86.2°C ± 0.2°C, with a 6.3% error from 92°C, the literature melting point of pure benzocaine. The crude product was then recrystallized to improve the purity of benzocaine and 57.4% was recovered. The new melting point range was measured at 89.1°C ± 0.3°C, which has a 3.15% error. The infrared spectrum of the recrystallized product was measured to further verify that the synthesized product was benzocaine.
Introduction
The discovery of benzocaine as a local anesthetic came out of necessity to
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Next, 1mL plus an additional 10 drops of 10% sodium carbonate was added drop-wise to the beaker until the solution reached a pH of 8. The precipitate formed (crude benzocaine product) was collected via vacuum filtration and washed with water during the transfer into the Hirsch funnel. The product was allowed to dry for one week after which the mass and melting point of the crystals were measured.
The crude product was then recrystallized in a Craig tube over a warm water bath (60-70°C) by adding methanol drop-wise until the solid completely dissolved. Eight drops of hot waster were then added to reform the precipitate, followed by subsequent addition of 15 methanol drops to re-dissolve the precipitate. The solution was then chilled in an ice bath and “seeded” with a spatula to induce crystallization. The recrystallized product was then collected via gravity filtration using an air vacuum to accelerate the process. An analytical balance was used to determine the mass of the purified product. The crystals were collected in two capillary tubes and a MelTemp device was used to measure the new melting point. A sample of crystals was run through the IR spectrometer to obtain the infrared spectra for the purified benzocaine product. The data and calculations sheets are attached to the report.
Results and
An Erlenmeyer flask was used to accommodate the largest volume of recrystallization solvent calculated and was cooled in an ice bath to increase the yield of crystals. The solid was collected by vacuum filtration and washed with a small amount of ice water. The product is then dried to a constant mass by use of an oven and weighed. A small amount of the unknown was compared to two samples of acetanilide and phenacetin for a melting point range to determine the identity. The temperature of the unknown was recorded when the first trace of liquid can be seen and when the unknown was completely liquid.
As a group, we obtained our salt mixture of calcium chloride and potassium oxalate, and weighed the mixture. We were able to make an aqueous solution from the mixture and distilled water. We boiled and filtered off the solution, leaving the precipitate. Once the precipitate was dried overnight, it was weighed and the mass was measured. Then we calculated the moles of the precipitate.
The mixture was transferred to an ice bath to crystallize the product, after which the product was collected by vacuum filtration on a Hirsch funnel, washing the flask with small aliquots of cold xylene and pouring the solution over the crystals, allowing the vacuum to thoroughly dry the product. Additional drying was achieved by transferring the product to filter paper and pressing the crystals to remove any excess moisture. The product was then weighed and a melting point determined. A comparative TLC was run in Hexanes:Ethyl Acetate solvent against maleic anhydride to verify the purity of the
The hydrobenzoin (meso) product of the benzil was isolated through the techniques of recrystallization and vacuum filtration. Because there NaBH4 was the limiting reagent in the experiment, 0.005604moles of NaBH4 should yield 1.2008g of hydrobenzoin (meso). The mass of the isolated product was 0.613g, resulting in a 51.1% yield. There are many reasons to account for the loss of 48.9% of
In this lab, liquid-liquid extraction was performed to isolate a mixture of benzocaine and benzoic acid. 2.0107 grams of the mixture was first weighed out for the trials. When HCl was added to the mixture for the first acid extraction of benzocaine, an emulsion formed during inversion and venting that prevented a defined separation of the two layers. 8 mL of water was therefore added before continuing the extraction. The addition of NaOH then turned the top aqueous layer basic, indicated by the pH strips that turned blue when tested. A vacuum filtration isolated 0.29 grams of benzocaine and a MelTemp apparatus measured the crystal’s melting point ranges to be 85.1C-87.4C. For the base extraction of benzoic acid, the aqueous layers were retrieved
The product was placed in a Craig tube and several drops of hot (100°C) solvent (50% water, 50% methanol, by volume) was added and heated until all of the crystals dissolved. The Craig tube was plugged and set in an Erlenmeyer flask to cool. Crystallization was induced once the mixture was at room temperature by scratching the inner wall of the tube. It was then placed into an ice bath for ten minutes until crystallization was complete. The tube was then
24) Separate the formed crystals (benzoin) and allow them to dry, then take the MP.
The product was then suspended in 2 ml of water with a stir rod in a 50 ml Erlenmeyer flask and heated to boiling. Water was added in one milliliter increments until all the product was dissolved (18 ml added total). The saturated solution was allowed to slowly cool, and gradual white crystal formation was observed. Recrystallized product was collected once more by suction filtration with the Hirsch funnel once crystallization ceased. Collected product dried on a watch glass for a week, weighed 0.14 g (1.2 mmol), and the melting point was 139°-141°
Abstract: One mixture of two unknown liquid compounds and one mixture of two unknown solid compounds were separated, isolated, purified, and characterized by boiling point. Two liquid unknowns were separated, isolated, and purified via simple distillation. Then, the process of an acid-base extraction and washing were used to separate two unknown compounds into two crude compounds: an organic acid and a neutral organic compound. Each crude compound was purified by recrystallization, resulting in a carboxylic acid (RCO2H) and a pure organic compound (RZ). The resulting mass of the pure carboxylic acid was 1.688g with a percent recovery of 31.80%, the boiling range was 244-245 °C, and its density was 2.0879g/mL. The resulting mass of the pure organic solid was 2.4902g with a percent recovery of 46.91%, the boiling range was 52.0-53.4°C, and its density was 1.5956 g/mL.
Pre-Lab: Analgesic drugs are known for reducing pain, while antiseptic drugs reduce symptoms such as fevers and swelling. However, some of these drugs can reduce both illnesses. To obtain a pure compound in these drugs, the scientist needs to separate the desired compound by taking advantage of the different physical and chemical properties. Such as; different boiling points, melting points and their solubility properties. To do this a chemist can also asses the differences between acidic and basic substances when they are added to water soluble mixtures. Within this current experiment I will asses the
After allowing the flask to cool to room temperature and cooling on ice, the product was collected and washed with 2-propanol (2ml) into a clean Hirsch funnel and was filtered using vacuum filtration. The triphenylphosphine oxide remained in the propanol solution, and the crystals were dried by drawing air through them. The mass, percentage yield and melting point of the product was obtained. The crystals were stored in a glass vial for next experiment.
The week after, a recrystallization was performed on the previous week’s crude product. The product ethereal solution was first heated on a steam bath until dry. During the heating, a beaker of methanol was collected and also placed on the steam bath. Once the product was dry, it was cooled to room temperature and then placed in an ice-water bath. The now boiling methanol was added to the crude crystals and a recrystallization was performed. Once completed, the now purified product was collected via Buchner vacuum filtration and stored in drawer to dry for a week. Afterwards, a melting point range of the purified product was obtained by using a Mel-temp apparatus. Lastly, an
In this review, the infusion of midazolam and propofol appear to provide similar sedation and recovery time is shorter in subject when sedated with propofol . When propofol combine with midazolam it gives synergistic effect which occurs when both drugs are given for i.v. sedation is caused by an increase in the free plasma concentration of one of the drug. In evidence 1, eight healthy volunteers were selected to obtain propofol concentration in the absence and presence of midazolam and vice versa. Volunteers received the drug in two sessions (A and B). In session A, volunteers received a propofol i.v.bolus dose of 1 mg/kg in 1 min which was followed by an infusion of 2.5 mg.kg-1.h-1 (= 41.7 μg kg-1.min-1) for 59 min. On the other hand, in session B the volunteers received the same propofol infusion plan as during session A, but now (TCI) directly target midazolam concentration (CT) of 125 ng/ml that was started 15 min the propofol administration. After the blood sample and assays, and statistical analysis, it result that in the presence of a mean midazolam concentration of 224.8 ± 41.6 ng/ml, the propofol concentrations were on average 25.1 ± 13.3 % which is higher as compared to when propofol was given as alone. In evidence 2, BIS value is been checked in volunteer receiving combination of midazolam and propofol, which result in subject remained receptive during the whole study.
The compound already presented an interesting in vitro activity in its initial tests and currently is thought to be one of the most active benzothiadiazine-derived AMPA-PAMs reported []. Further conducted intracerebral microdialysis experiments allowed detection of micromolar concetration of 1 in mouse nucleus accumbens (NAc) dialysates. It means that the compound is able to cross blood-brain barrier (BBB) after intraperitoneal injection (ip) (see section paragraph). Intracerebral microdialysis is a known experiment that can be applied to evaluate in vivo compound’s p pharmacokinetic (PK) and pharmacodynamic (PD) profile. Nevertheless, it is crucial the compound remains in the specific brain of interest for a sufficient time and at the appropriate to evoke its function and achieve the desired effect. Therefore, examination in vivo of the novel compounds stability plays pivotal role here. In fact, chemical degradation of compound can lower its sufficient concentration below the therapeutic dose. Moreover, as explained in detail in introductory paragraphs, the AMPA-PAM activity usually resides only in one enantiomer
The intravenous anaesthetic propofol is currently the least emetogenic general anaesthetic. These medications are thought to stimulate the chemoreceptor trigger zone (CTZ). This area is on the floor of the fourth ventricle and is effectively outside of the blood-brain barrier. This makes it incredibly sensitive to toxin and pharmacological stimulation. There are multiple neurotransmitters such as histamine, dopamine, serotonin, acetylcholine, and the more recently discovered neurokinin-1 (substance P) [2].