a 5 of | OS & College sree oe Page 69 of 96 Document: LABORATORY MANUAL re: PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Name: Section: Date Performed: Score: Learning Activity No. 6 IDENTIFICATION OF ANALGESIC USING TLC Specific Learning Objectives: 1. 2 3. [substance Rf value lodine Reaction Inference Acetylsalicylic acid Acetaminophen Ibuprofen Naproxen U-1 U-2 U-3 U-4ae : i Te Cat tres mcm So i! | € S Setar chemi ae a ‘Davao City Revision Date: | October 2019 fester! eactcne a SST ia Pe ATA RS GER RT Draw the observed chromatographs using colored pencils and label it with Rf value and identified compounds. Conclusion: Learning Evaluation: 1 | ' \ | | \ ' \ ' ' \ 1 \ \ | \ | ! \ \ ' | ! ' ' | | | ! | \ I | | | \ | | | | ' ' I narrin . | 1. Whatis the stationary phase and what is the mobile phase in this experiment? | | |College of Pharmacy and Ctiemistry ems very ofthe Immaculate Conception Date: | October 2010 pee Revised by: | Brteta,Ferllen Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY 2, Why is a pencil (not a pen) used to mark the position of the spots? 3. Why is an Rf value rather than the distance the identify a substance by TLC? 4, What is co-spotting? = a. Aspirin b. Acetaminophen c. Caffeine ' ' 1 | | ' ' 1 | \ 1 | | 1 ' | | 1 | | I 1 | | 1 component by TLC? ' | | 1 | | 1 | 1 1 | | I | 1 | i d. Ibuprofen ' 1 1 | | y ‘spot moved used to help . Why is co-spotting a good technique for determining the’ identity of a Write the Chemical:names and draw the Structures of the following:$e College of Pharmacy and Chemis Page 72 0f 96 SeneraetPharmey an chenay Davao cy Revision Date: | October 2019 Revised ty: _ | Brieta, Ferllen Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Name: Section: Date Performed: Score: Learning Activity No. 7 PREPARATION AND. IDENTIFICATION OF METHYL SALICYLATE Specific Learning Objectives: 1. 2 3. CHEMICAL REACTION INVOLVED. Write the complete reaction, including the intermediate products in the reaction. Table 1. DATA TABLE Volume of oil of methanol Volume salicylic acid Mass of oil of methanol Mass of salicylic acid Actual Yield (mass of product collected) Theoretical Yield (by calculation) Percentage YieldCollege of Pharmacy and Chemistry Page 73 of 96 University of the Immaculate Conception 0 City Revised by: Revision Date: | October 2019 Brfeta, Ferllen Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Calculation of Theoretical Yield: Calculation of Percentage Yield: Table 2. Percentage Yield = actual yield theoretical yield * ! 00 IDENTIFICATION TEST RESULTS Physical Test Color: Odor : 1 1 1 | 1 1 1 1 1 1 1 1 1 I | 1 1 1 1 1 1 1 1 1 1 | | 1 ' t, 1 | \ | \ | ! | ! 1 ' 1 i 1 | | I ss Appearance: Melting range: Chemical Test Test Result / Observation Inference (+ or -)College of Pharmacy and Chemistry Page 74 of 96 Utivesy of ie Immaculate Concepon Revision Date: | October 2019 Davao chy Revised by: | Brieta, Ferfien Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Reaction with ferric chloride solution. Table 3. Fill in the needed data to complete the table. Table of Physical and Chemical Constants of Reactants and Products Compound nar | melting | Hazard and N formula/ " Density Point Safety — Structure 7 Information Salicylic acid Methanol Hexane 1 ! ! 1 | | | 1 1 ' 1 1 | | 1 | 1 1 | 1 ' ' | | Chemical ! 1 i | 1 1 \ 1 1 | | I | | 1 1 I 1 1 I | | | |College of Pharmacy and Chemistry Page 75 of 96 University ofthe Immaculate Conception Davao Cty Revision Date: | October 2019 Revised by: | Brleta, Ferien Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Learning Evaluation: 1, Whats the function of adding sodium carbonate during the reaction? 2. Determine the two additional byproducts produced in the synthesis of methyl salicylate. 3. Discus the hydrolysis reaction and differentiate its two types. 4. Enumerate the pharmaceutical uses of methyl salicylateCollege of Pharmacy and Chemistry University of the Immaculate Conception Davao City Document: LABORATORY MANUAL Tile: Name: ____ Section: Date Performed: . Score: Learning Activity No. 8 SYNTHESIS OF ACETYLSALICYLIC ACID Specific Learning Objectives: 1. 2 3. Weight of Dried Sample: Theoretical Yield: Percentage yield:College of Pharmacy and Chemistry Page 77 of 96 University of the Immaculate Conception Davao City Revision Date: | October 2019 Revised by: _| Brieta, Ferllen Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Aspirin Quality Test tube | Observations (Colors | Observations (Colors | Inference ' J (write the produced before | produced after adding ' contents) adding FeCl3) FeCcl3) 1 1 fa | 1 a2 a: 1 3 4 Melting point of Synthesized sample: Melting point from USP/NF: Inference: Conclusion: are= 1 1 1 | 1 1 I ' ! 1 i i I | 1 l 1 1 1 1 1 1 1 ! 1 | 1 t 1 1 ! 1 1 | \ \ \ i 1 1 ' \ 1 ees eran ncn sera nn 5 LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Learning Evaluation: 1. Normally, you measure reactants to at least two signifi it not necessary to measure the volume of acetic significant figures? What is the theo figures). icant figures, Why is anhydride to two retical yield of aspirin (in two significant 2. Why is the aspirin washed with cold water? 3. According to the data in the Merck Index, if 1.0 & Of aspirin is dissolved in 100 mL of water at 37 °C , how much aspirin will precipitate out of solution when it is cooled to 25°C ? 4. A polymeric material, which is a polyester, is formed in this reaction. Polyesters are often made from dicarboxylic acids and diols. In this case, one molecule (salicylic acid) provides both the “alcohol” and the carboxylic acid. Write a structure for the ester formed from acetic acid and ethanol.College of Pharmacy and Chemistry Page 79 of 96 University ofthe Immaculate Concopt eee evo Date ‘October 2019 Revised by: _| Brieta, Ferlien Mae LABORATORY MANUAL, Te: PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Name: Sectior Date Performed: Learning Activity No. 9 PREPARATION OF ACETAMINOPHEN Specific Learning Objectives: 1 2 3. Weight of Dried Sample: Theoretical Yield: Percentage yield: L Inference: Conclusion:College of Pharmacy and Chemistry eee University ofthe Immaculate Conception Daveo chy Revision Date: | October 2019 Revised by: | Brieta, Ferflen Mac Document: LABORATORY MANUAL [te 400 PHARMACEUTICAL & EDICHNAL ORGANIC CHEMISTRY Learning Evaluation: 1. What is the mechanism of action of acetaminophen? a. The antipyretic activity is exerted by blocking the effects of endogenous Pyrogen on the hypothalamic heat-regulating center. b. It causes heat dissipation by vasodilation and an increased in peripheral blood flow. ¢. Itisa reversible inhibitor of cyclooxygenase. d. Allof the above. 2. How does acetaminophen produce its analgesic effect? a. By direct action on the pain threshold. b. By inhibition of PG synthesis. ¢. By inhibition of the synthesis or action of chemical mediators. d. All of the above. 3. What is the mechanism of acetaminophen induced hepatotoxicity in acute intoxication? a. Acetaminophen binds covalently to sulhydryl group on_ tissue macromolecule. b. Oxidized metabolite of p-aminophenol binds covalently to sulhydryl group on tissue.macromolecule. ¢. Acetaminophen induces cytochrome P 450 from microsome. d. Oxidized metabolite of p-aminophenol induces cytochrome P 450 from microsome. 4. What is the main excretion route of acetaminophen? a. Urinary excretion. b. Bile acid. c, Sweat. d. None of the above 5. Which of the followings, is/are the major biotransformation process of acetaminophen in human body? a. Oxidative metabolism. b. Glucuronidation and sulfate conjugation. ¢c. Reduction and electron transfer d. Dehydrogenation and deamination.College of Pharmacy and Chemistry Page 81 of 96 University of| culate Conception oo Revision Date: | October 2019 Revised by: | Brieta, Ferien Mae LABORATORY MANUAL PCH 400 PHARMACEUTICAL & MEDICINAL ORGANIC CHEMISTRY Name: Date Performed: 1 2. 3. Learning Activity No. 10 PREPARATION OF BENZOCAINE Specific Learning Objectives: Weight of Dried Sample: Section: Score: Theoretical Yield: L Melting point of Synthesized sample: Melting point from USP/NF: Inference: Conclusion:Boao Sen eS enn fs on ean e 52-2 2-25 t = 2-5-5 ===} College of Pharmacy and Chemistry University ofthe Immaculate Conception Davao City Revised by: | Brieta, Ferllen Mae _[exBORATORY MANUAL Tie: PCH 400 PHARMACEUTICAL. & MEDICINAL ORGANIC CHEMISTRY Learning Evaluation: 1, Discuss the primary mechanism of action of local anesthetics. 2. Rationale for adding epinephrine to a local anesthetic solution: a. reduced local anesthetic systemic absorption b. increased anesthetic concentration near nerve fibers cc. reduced duration of conduction blockade d. all of the above 3. Primary side effect/toxicities associated with local anesthetic use: a. allergic reactions b. systemic toxicity c, both d. neither 4. Clinical use(s) of EMLA applications: a. arterial cannulation b. venipuncture c. myringotomy d. lumbar puncture 5. Local anesthetic lipophilicity and effectiveness of epinephrine on local anesthesia: : a. more lipophilic anesthetics benefit most by epinephrine in addition to local anesthetic solutions . b. more lipophilic anesthetics benefit least by epinephrine in addition to local‘anesthetic solutions