Leigh Burdick, Erica Schandler, Theodora Leventis Oxycodone Leigh Burdick, Erica Schandler, Theodora Leventis

Oxycodone: Structure/Uses Strong narcotic pain reliever (morphine, codeine, hydrocodone) Used in clinical medicine as both an analgesic and antitussive agent Decreases discomfort by increasing pain tolerance Intermediate synthon in synthesis of narcotic antagonists such as naloxone and naltrexone Cotton, S. “Codeine and Oxycodone­-Painkillers that become addictive” Molecule of the Month. December 2015. <http://www.chm.bris.ac.uk/motm/codeine/codeineh.htm> (accessed 6 Mar 2018)

Oxycodone: Abuses Highly addictive–should not be used more than prescribed (typically 5-15 mg every 6 hours) LD50: 320 mg/kg person’s weight (not combined with alcohol or other drugs) Higher tolerance results in a person requiring more of the drug to receive the same reinforcement feeling. Continued abuse of the drug is used to prevent withdrawal symptoms Cooper, Z.D.; Johnson, K.W.; Vosburg, S. K.; Sullivan, M.A.; Manubay, J.; Martinez, D.; Jones, J.D.; Saccone, P.A.; Comer, S.D. “Effects of ibudilast on oxycodone-induced analgesia and subjective effects in opioid-dependent volunteers” National Center for Biotechnology Information. 2017, 178, 340-347.

OxycodonE: Synthesis Starting Material: Thebaine Oxidation by m-CPBA Intermediate: 1,4-hydroxycodeinone Hydrogenation by H2/Pd Product: Oxycodone Cotton, S. “Codeine and Oxycodone” 2015. http://www.chm.bris.ac.uk/motm/codeine/codeineh.htm (Accessed 6 March 2018)

Oxycodone 1H NMR Spectrum ppm Functional Group 2.4 ketone 3.9 alcohol 4.7 Vinylic carbon 6.7 3o amine 7.3 aromatic Pfleger, K.; Maurer, H.; Weber, A. “Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Part I and II” Mass Spectra Indexes. 1985.

Oxycodone IR Spectrum Significant Peaks (cm-1) Functional Group 1035 C-N 1278 C-O-C 1614 C=C 1726 C=O 3205 O-H Pfleger, K.; Maurer, H.; Weber, A. “Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Part I and II” Mass Spectra Indexes. 1985. S2.

Oxycodone Mass Spectrum Oxycodone shows significant peaks at: 70, 140, 230, 258, 315 m/z Pfleger, K.; Maurer, H.; Weber, A. “Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Part I and II” Mass Spectra Indexes. 1985. S2. Tavakol, H.; Esfandyari, M.; Taheri, S.; Heydari, A. “Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: A combined experimental and theoretical study” National Center of Biotechnology Information. 2011. 79, 574-582.

Oxycodone: Function Mesolimbic System: reward system of brain Ventral Tegmental Area (VTA) Nucleus Accubens (Nac) Tolerance: receptors become less responsive Causes further use of oxycodone Withdrawal symptoms Kosten, T.; George, T.P. “The Neurobiology of Opioid Dependence: Implications for Treatment” National Center for Biotechnology Information. 2002. 1, 13-20.

Oxycodone: Merits Used for the management of moderate to severe pain Generally safe when taken in small amounts as recommended by a doctor, however affects nervous system like heroin– interact with opioid receptors in nerve cells around body and brain Wiseman, Ben. “The Family That Built An Empire Of Pain” The New Yorker. October 2017. <https://www.newyorker.com/magazine/2017/10/30/the-family-that-built-an-empire-of-pain> (accessed 7 Mar 2018)

Oxycodone: Deficiencies Chemical derivative of heroin–twice as powerful as morphine. Since 1999, 200,000 deaths in America have been due to OxyContin (oxycodone hydrochloride) and other opioids. OxyContin prescription is expensive, addicts turn to heroin (4/5 people who try heroin have started with painkillers) Side effects: respiratory arrest, apnea, circulatory depression, death. Tablets must be swallowed whole, since broken or chewed tablets release the drug in too concentrated levels in the body, which leads to overdose “Opioids” National Institute on Drug Abuse (NIDA). May 2017. <https://www.drugabuse.gov/publications/opioids> (accessed 7 Mar 2018)

Summary: Oxycodone Haiku Oh Oxycodone Do not be the death of me FUNctional groups…NOT