Mirfentanil

Mirfentanil
Names
Preferred IUPAC name
N-[1-(2-Phenylethyl)piperidin-4-yl]-N-pyrazinylfuran-2-carboxamide
Other names
MS-32, NIH-10647
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH C069209
PubChem CID
UNII
InChI
  • InChI=1S/C22H24N4O2/c27-22(20-7-4-16-28-20)26(21-17-23-11-12-24-21)19-9-14-25(15-10-19)13-8-18-5-2-1-3-6-18/h1-7,11-12,16-17,19H,8-10,13-15H2 ☒N
    Key: BJZZDOLVVLWFHN-UHFFFAOYSA-N ☒N
  • InChI=1/C22H24N4O2/c27-22(20-7-4-16-28-20)26(21-17-23-11-12-24-21)19-9-14-25(15-10-19)13-8-18-5-2-1-3-6-18/h1-7,11-12,16-17,19H,8-10,13-15H2
    Key: BJZZDOLVVLWFHN-UHFFFAOYAN
SMILES
  • C1CN(CCC1N(C2=NC=CN=C2)C(=O)C3=CC=CO3)CCC4=CC=CC=C4
Properties
Chemical formula
 C22H24N4O2
Molar mass 376.460 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Mirfentanil is a fentanyl derivative with strong selectivity for the μ opioid receptor. At lower doses, it antagonizes the analgesic effects of alfentanil and substitutes for naloxone in morphine-treated monkeys; however, it also reverses naloxone-precipitated withdrawal in pigeons trained to discriminate morphine from naloxone.[1]

At high doses, it exhibits analgesic activity which is not fully reversed by opioid antagonists, suggesting that the drug has both opioid and non-opioid mechanisms of action.[1][2]

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs 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.[3]

Synthesis

Mirfentanil was synthesized via acylation of the product of the reaction of 2-chloropyrazine and 1-(2-phenylethyl)-4-piperidinone oxime with 2-furoyl chloride.[4]

See also

References

  1. 1 2 France, CP; Winger, G; Medzihradsky, F; Seggel, MR; Rice, KC; Woods, JH (Aug 1991). "Mirfentanil: pharmacological profile of a novel fentanyl derivative with opioid and nonopioid effects". Journal of Pharmacology and Experimental Therapeutics. 258 (2): 502–10. PMID 1650830.
  2. ↑ Carr, DJ; Brockunier, LL; Scott, M; Bagley, JR; France, CP (Aug 1996). "Mirfentanil antagonizes morphine-induced suppression of splenic NK activity in mice". Immunopharmacology. 34 (1): 9–16. doi:10.1016/0162-3109(95)00051-8. PMID 8880221.
  3. ↑ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
  4. ↑ Jerome R. Bagley; Wynn, Richard; Rudo, Frieda; Doorley, Brian; Spencer, Kenneth; Spaulding, Theodore (1989). "New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry. 32 (3): 663–71. doi:10.1021/jm00123a028. PMID 2563773.
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