Basic information
- CAS
117523-47-4- Standard SMILES
O=C(c1ccco1)N(c1cnccn1)C1CCN(CCc2ccccc2)CC1- InChIKey
BJZZDOLVVLWFHN-UHFFFAOYSA-N- Molecular formula
- C22H24N4O2
- Average molar mass
- 376.5 g/mol
- Monoisotopic mass
- 376.18992602
Overview
Mirfentanil is a derivative of fentanyl that presents high selectivity for the mu 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. 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.
Names & identifiers
- Preferred name
- Mirfentanil
- IUPAC
- N-[1-(2-phenylethyl)piperidin-4-yl]-N-pyrazin-2-ylfuran-2-carboxamide
- English name
- Mirfentanil
- Molecular formula
- C22H24N4O2
- Molecular weight
- 376.45
Names & synonyms
MirfentanilMirfentanilo117523-47-4MirfentanilumMIRFENTANYLMS 32 (RECEPTOR BINDER)Q2U943H24POHM 10579DTXSID10151799A 35082-Furancarboxamide, N-(1-(2-phenylethyl)-4-piperidinyl)-N-pyrazinyl-N-[1-(2-phenylethyl)piperidin-4-yl]-N-(pyrazin-2-yl)furan-2-carboxamide
Show more names
A-3508N-(2-Pyrazinyl)-N-(1-phenethylpiperidin-4-yl)furan-2-carboxamideN-(Pyrazin-2-yl)-N-(1-phenethylpiperidin-4-yl)furan-2-carboxamideN-(1-phenethylpiperidin-4-yl)-N-(pyrazin-2-yl)furan-2-carboxamide2-Furancarboxamide, N-[1-(2-phenylethyl)-4-piperidinyl]-N-2-pyrazinyl-
N-(1-(2-phenylethyl)piperidin-4-yl)-N-(pyrazin-2-yl)furan-2-carboxamideMS-32RefChem:159036DTXCID7074290NIH-10647N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamideMS32Mirfentanil [INN]
Database identifiers
- CAS
117523-47-4
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 62.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 489
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 206 · 206-207 °C
- Boiling point
- 538.3 · 538.3±50.0 °C(Predicted)
- Density
- 1.222 · 1.222±0.06 g/cm3(Predicted)
- pka
- 8.59 · 8.59±0.10(Predicted)
- FDA UNII
- 2 U943H24P · Q2U943H24P
Chemistry & industry
Applications
UsesAnalgesic.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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