503091-11-0

Basic information

• Product Name: C₂₅H₂₇NO₄
• CAS NO: 503091-11-0
• Molecular Weight: 405.494
• Mol File: 503091-11-0.mol

Chemical Properties

• CAS DataBase Reference: C₂₅H₂₇NO₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₅H₂₇NO₄(503091-11-0)
• EPA Substance Registry System: C₂₅H₂₇NO₄(503091-11-0)

Safety Data

• Hazardous Substances Data: 503091-11-0(Hazardous Substances Data)

Upstream product

• 33522-95-1 noroxymorphone 
• 637-59-2 1-Bromo-3-phenylpropane 
• 76-42-6 Oxycodone 
• 76-41-5 oxymorphone 

Relevant articles and documents

Benzylideneoxymorphone: A new lead for development of bifunctional mu/delta opioid receptor ligands

Opioid analgesic tolerance remains a considerable drawback to chronic pain management. The finding that concomitant administration of delta opioid receptor (DOR) antagonists attenuates the development of tolerance to mu opioid receptor (MOR) agonists has led to interest in producing bifunctional MOR agonist/DOR antagonist ligands. Herein, we present 7-benzylideneoxymorphone (6, UMB 246) displaying MOR partial agonist/DOR antagonist activity, representing a new lead for designing bifunctional MOR/DOR ligands.

Opioids and efflux transporters. Part 4: Influence of N-substitution on P-glycoprotein substrate activity of noroxymorphone analogues

The efflux transporter protein P-glycoprotein (P-gp) is capable of affecting the central distribution of diverse neurotherapeutics, including opioid analgesics, through their active removal from the brain. P-gp located at the blood brain barrier has been implicated in the development of tolerance to opioids and demonstrated to be up-regulated in rats tolerant to morphine and oxycodone. We have previously examined the influence of hydrogen-bonding oxo-substitutents on the P-gp-mediated efflux of 4,5-epoxymorphinan analgesics, as well as that of N-substituted analogues of meperidine. Structure-activity relationships (SAR) governing N-substituent effects on opioid efficacy is well-established, however the influence of such structural modifications on P-gp-mediated efflux is unknown. Here, we present SAR describing P-gp recognition of a short series of N-modified 4,5-epoxymorphinans. Oxymorphone, naloxone, naltrexone, and nalmexone all failed to demonstrate P-gp substrate activity, indicating these opioid scaffolds contain structural features that preclude recognition by the transporter. These results are examined using mathematical molecular modeling and discussed in comparison to other opioid scaffolds bearing similar N-substituents.