76-42-6 Usage
Description
Oxycodone (Item No. 15465) is an analytical reference material categorized as an opioid. Oxycodone is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.
Uses
Analgesic (narcotic).
Definition
oxycodone: An opioid, C18H21N2,similar in structure to codeine butwith a –OH group in codeine replacedby a carbonyl group. It is ananalgesic often used for the treatmentof chronic pain. It is also usedillegally and is a controlled substancein most countries.
Biological Functions
Oxycodone is nearly 10 times as strong as codeine,
with absorption equal to that of orally administered morphine.
Neither hydromorphone nor oxycodone is approved
for use in children, and hydromorphone is contraindicated
in obstetrical analgesia and in asthmatics.
General Description
Oxycodone is synthesized from the natural opium alkaloidthebaine. Oxycodone is the 14 beta-hydroxyl version of hydrocodone.This additional functional group gives oxycodonegreater potency (1.5 times orally) than hydrocodone presumablyby increasing receptor affinity. The oral bioavailabilityof oxycodone is 65% to 87%. The metabolism of oxycodonefollows the similar pattern of opioid metabolism withN-demethylation, O-demethylation, and their glucuronides allidentified. Per the manufacturer, the analgesic effect of oxycodonecorrelates well with oxycodone plasma concentrations,not the minimal amount of oxymorphone formed, thusoxycodone is not assumed to be a prodrug. There are no largescalestudies of oxycodone used for analgesia in CYP2D6poor metabolizers that can confirm this.Oxycodone is marketed in combination with acetaminophen(Percocet), aspirin (Percodan), and ibuprofen(Combunox). It has been available for over 50 years as animmediate-release tablet, and in 1995 an extended-releasetablet was approved by the FDA (OxyContin). OxyContin ismanufactured in eight strengths from 10 to 160 mg, and thehigh-dose preparations quickly became attractive to drugabusers. The extended-release tablets are crushed and theninjected or snorted to give an immediate high. The DrugAbuse Warning Network (DAWN) is a public health surveillancesystem that monitors drug-related emergency roomvisits and drug-related deaths. In 1995, they estimated that598,542 emergency room visits involved the nonmedical useof a pharmaceutical (e.g., antidepressant, anxiolytic, stimulant).Of these ER visits, 160,363 visits were attributed toopiates with an estimated 42,810 involving oxycodone or anoxycodone combination. Methadone and hydrocodone/combinationswere estimated to be similar to oxycodone.
Pharmacology
Oxycodone is a potent semisynthetic opioid that has been in use for many
years. In addition to actions at the MOP receptor, it may also have analgesic
effects mediated via the KOP receptor, resulting in incomplete crosstolerance
with morphine. It has a good oral bioavailability, and its plasma
concentrations are more predictable than those of morphine after oral
administration. It is available in both long- and short-acting oral
preparations and, more recently, in a parenteral formulation. Oral oxycodone
is roughly 1.5 times more potent than oral morphine.
Safety Profile
Poison by intraperitoneal route. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 76-42-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 76-42:
(4*7)+(3*6)+(2*4)+(1*2)=56
56 % 10 = 6
So 76-42-6 is a valid CAS Registry Number.
InChI:InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3
76-42-6Relevant articles and documents
Synthesis of (-)-Oxycodone
Kimishima, Atsushi,Umihara, Hirotatsu,Mizoguchi, Akihiro,Yokoshima, Satoshi,Fukuyama, Tohru
, p. 6244 - 6247 (2014)
Our novel synthetic route to (-)-oxycodone, a semisynthetic opioid analgesic, features a palladium-catalyzed direct intramolecular arylation of an aryl bromide, oxidative dearomatization of a dihydrophenanthrenol, formation of a benzylic quaternary carbon by an intramolecular Michael addition of a malonate moiety, and construction of the morphinan skeleton via a Hofmann rearrangement/lactamization cascade.
Structural elucidation and synthesis of a dimeric degradation impurity during long-term stability studies of oxycodone hydrochloride injection
Du, Wei,Jin, Jian,Liang, Lingzhi,Liu, Bifeng,Liu, Xin,Ma, Yurong,Ren, Xia,Zhang, Guisen,Zhuang, Tao
, p. 18651 - 18658 (2021/10/25)
Oxycodone is one of the most prescribed narcotic medications for the treatment of moderate to severe pain in clinical practice. During long-term stability studies of oxycodone hydrochloride for injection performed as per ICH Q1A (R2) guidelines, an unknown degradation product, impurity-I, increased over time and reached a level of 0.21% after 24 months, based on the results of HPLC analysis. The observed impurity was preliminarily characterized as an oxycodone aldol dimer by using two-dimensional (2D) liquid chromatography (LC) coupled with quadrupole time-of-flight mass spectrometry (QTOF MS/MS) analysis. Impurity-I was synthesized and its molecular structure confirmed based on detailed analysis of 1D-NMR (1H, 13C, and DEPT) and 2D-NMR (1H-1H COSY, HSQC, and HMBC) spectroscopy data. The plausible mechanism for the formation of impurity-I was an aldol condensation reaction under weakly acidic conditions. In addition, the potential toxicity of impurity-I was assessed by in silico toxicity predictions using the TOPKAT software.
Electrochemical N-Demethylation of 14-Hydroxy Morphinans: Sustainable Access to Opioid Antagonists
Cantillo, David,Glotz, Gabriel,Kappe, C. Oliver
supporting information, p. 6891 - 6896 (2020/09/15)
The most challenging step in the preparation of many opioid antagonists is the selective N-demethylation of a 14-hydroxymorphinan precursor. This process is carried out on a large scale using stoichiometric amounts of hazardous chemicals like cyanogen bromide or chloroformates. We have developed a mild reagent- and catalyst-free procedure for the N-demethylation step based on the anodic oxidation of the tertiary amine. The ensuing intermediates can be readily hydrolyzed to the target nor-opioids in very good yields.
NOVEL OPIOID COMPOUNDS AND USES THEREOF
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Paragraph 0519-0523, (2019/09/12)
This invention relates to novel opioid derivatives of Formula I: or a pharmaceutically acceptable salt or solvate thereof, wherein R1, R3, R4 and Z are as defined herein in the disclosure. The invention also relates to the use of such compounds for the treatment or prevention of, for example, pain.
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