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

2. 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 < (accessed 6 Mar 2018)

3. 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,

4. OxycodonE: Synthesis Starting Material: Thebaine Oxidation by m-CPBA
Intermediate: 1,4-hydroxycodeinone
Hydrogenation by H2/Pd
Product: Oxycodone
Cotton, S. “Codeine and Oxycodone” (Accessed 6 March 2018)

5. 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

6. 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 S2.

7. 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 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 ,

8. 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 ,

9. 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 < (accessed 7 Mar 2018)

10. 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 < (accessed 7 Mar 2018)

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