Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Opioid Analgesics: Synthetic and Semisynthetic Opioids01:15

Opioid Analgesics: Synthetic and Semisynthetic Opioids

Synthetic and semisynthetic opioids are pivotal in pain management and tackling opioid addiction. Semisynthetic opioids, including morphinans (morphine derivatives), oxycodone, oxymorphone, hydrocodone, and hydromorphone, have improved pharmacokinetic profiles compared to morphine. Additionally, heroin and 6-MAM (6-Monoacetylmorphine) show better CNS penetration than morphine due to heightened lipid solubility. Hydromorphone, a potent opioid, undergoes hepatic metabolism to form the active...
Opioid Analgesics: Morphine and Other Natural Cogeners01:20

Opioid Analgesics: Morphine and Other Natural Cogeners

Opioids are a class of drugs that mimic endogenous opioid peptides and act on opioid receptors, and help in pain relief. These compounds are classified as natural, synthetic, or semi-synthetic. Natural opioids, like morphine, codeine, and thebaine, are derived from the opium poppy plant (Papaver somniferum or Papaver album) and are termed opiates. Synthetic opioids are artificial, while semi-synthetic opioids combine natural and synthetic compounds. Morphine, a prototypical opioid, possesses a...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
Opioid Receptors: Overview01:22

Opioid Receptors: Overview

Opioid receptors, including the mu (μ, MOR), delta (δ, DOR), and kappa (κ, KOR) types, belong to the rhodopsin family of G protein-coupled receptors. These receptors are located throughout the central and peripheral nervous systems and in non-neuronal tissues such as macrophages and astrocytes. Opioid receptor ligands can be categorized into agonists or antagonists. Highly selective agonists include [d-Ala2, MePhe4, Gly(ol)5]-enkephalin or DAMGO for MOR, [D-Pen2, D-Pen5]-enkephalin or DPDPE for...
IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Vesicular monoamine transporter-2 inhibitor JPC-141 prevents methamphetamine-induced dopamine toxicity and blocks methamphetamine self-administration in rats.

Biochemical pharmacology·2024
Same author

Thiadiazolidinone (TDZD) Analogs Inhibit Aggregation-Mediated Pathology in Diverse Neurodegeneration Models, and Extend <i>C. elegans</i> Life- and Healthspan.

Pharmaceuticals (Basel, Switzerland)·2023
Same author

High flux novel polymeric membrane for renal applications.

Scientific reports·2023
Same author

Deuterated buprenorphine retains pharmacodynamic properties of buprenorphine and resists metabolism to the active metabolite norbuprenorphine in rats.

Frontiers in pharmacology·2023
Same author

Parthenolide induces rapid thiol oxidation that leads to ferroptosis in hepatocellular carcinoma cells.

Frontiers in toxicology·2023
Same author

Characterizing the Access of Cholinergic Antagonists to Efferent Synapses in the Inner Ear.

Frontiers in neuroscience·2021

Related Experiment Video

Updated: May 17, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Oxycodone N-oxide.

Vijayakumar N Sonar1, Sean Parkin, Peter A Crooks

  • 1Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|November 6, 2012
PubMed
Summary

This study details the synthesis of a novel oxycodone N-oxide derivative. The compound was prepared in high purity and its crystal structure confirmed a new chiral center at the 17-position.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Crystallography

Background:

  • Oxycodone is an opioid analgesic with a well-defined chemical structure.
  • Derivatization of existing pharmaceuticals can lead to novel compounds with altered properties.
  • Understanding molecular interactions and stereochemistry is crucial in drug development.

Purpose of the Study:

  • To synthesize a diastereomerically pure N-oxide derivative of oxycodone.
  • To characterize the synthesized compound using crystallographic methods.
  • To investigate the stereochemistry and intermolecular interactions of the new molecule.

Main Methods:

  • Reaction of oxycodone with 3-chloroperbenzoic acid.
  • Purification via crystallization from chloroform.

More Related Videos

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
06:06

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

Related Experiment Videos

Last Updated: May 17, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
06:06

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

  • X-ray crystallography for structural determination.

    • Main Results:

    • Successful synthesis of (5R,9R,13S,14S,17R)-14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-one N-oxide.
    • Confirmation of intramolecular O-H···O hydrogen bonding (2.482 Å).
    • Identification of weak intermolecular C-H...O interactions and van der Waals forces contributing to crystal stability.
    • Determination of a new R-configuration at the 17-position chiral center.

    Conclusions:

    • A novel oxycodone N-oxide derivative was synthesized and structurally elucidated.
    • The compound exhibits specific intramolecular hydrogen bonding and intermolecular interactions.
    • The stereochemical outcome of the synthesis established a new chiral center with R-configuration.