Ohmefentanyl

Source: Wikipedia, the free encyclopedia.
Ohmefentanyl
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide
JSmol)
  • CCC(=O)N(c1ccccc1)C2CCN(CC2C)CC(O)c3ccccc3
  • InChI=1S/C23H30N2O2/c1-3-23(27)25(20-12-8-5-9-13-20)21-14-15-24(16-18(21)2)17-22(26)19-10-6-4-7-11-19/h4-13,18,21-22,26H,3,14-17H2,1-2H3 checkY
  • Key:FRPRNNRJTCONEC-UHFFFAOYSA-N checkY
  (verify)

Ohmefentanyl (also known as β-hydroxy-3-methylfentanyl, OMF and RTI-4614-4)

μ-opioid receptor.[2][3]

There are eight possible

stereoisomers, which are named F9201–F9208. Researchers are studying the different pharmaceutical properties of these isomers.[8]

The 4″-fluoro analogue (i.e., substituted on the phenethyl ring) of the 3R,4S,βS isomer of ohmefentanyl is one of the most potent opioid agonists yet discovered, possessing an analgesic potency approximately 18,000 times that of morphine.[9] Other analogues with potency higher than that of ohmefentanyl itself include the 2′-fluoro derivative (i.e., substituted on the aniline phenyl ring), and derivatives where the N-propionyl group was replaced by N-methoxyacetyl or 2-furamide groups, or a carboethoxy group is added to the 4-position of the piperidine ring. The latter is listed as being up to 30,000 times more potent than morphine.[10]

Side effects of

respiratory depression, which can be life-threatening. Illicitly used fentanyl analogues have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[11]

The chemical structure of fentanyl has been used as a basis in modern chemistry for the discovery and nomenclature of many new fentanyl analogues, sometimes called 'fentalogues'.
Molecular structure of four of the eight ohmefentanyl isomers
Molecular structure of all of the eight ohmefentanyl isomers

Synthesis

Ohmefentanyl Synthetic Pathway
Ohmefentanyl Synthetic Pathway

See also

References

  1. PMID 1646357
    .
  2. PMID 7739013
    .
  3. PMID 7658453
    .
  4. ^ H. D. Banks, C. P. Ferguson (September 1988). "The Metabolites of Fentanyl and its Derivatives" (PDF). U.S. Army Chemical Research, Development and Engineering Center, Aberdeen Proving Ground, MD. Archived (PDF) from the original on July 14, 2014.
  5. PMID 6264594
    .
  6. PMID 6679170
    .
  7. PMID 10901279
    .
  8. PMID 15051423
    .
  9. PMID 12779044
    .
  10. ISSN 0929-8673
    .
  11. PMID 25976511
    .

External links
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