N-Phenethylnormorphine

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N-Phenethylnormorphine
N-Phenethylnormorphine.svg
Systematic (IUPAC) name
3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
Identifiers
PubChem CID: 46908217
Chemical data
Formula C24H25NO3
Molecular mass 375.459 g/mol
  • c6ccccc6CCN4CCC25C1Oc3c2c(ccc3O)CC4C5C=CC1O
  (verify)

N-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl.[1] It is around eight to fourteen times more potent than morphine as a result of this modification,[2] in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as antagonists.[3] Binding studies have helped to explain the increased potency of N-phenethylnormorphine, showing that the phenethyl group extends out to reach an additional binding point deeper inside the mu opioid receptor cleft, analogous to the binding of the phenethyl group on fentanyl.[4][5]

See also

References

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