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Mu-opioid receptor agonists
N-Phenethylnormorphine
Другие языки:

N-Phenethylnormorphine

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N-Phenethylnormorphine
N-Phenethylnormorphine.svg
Identifiers
  • 3,6-dihydroxy-7,8-didehydro-4,5α-epoxy-17-(2-phenylethyl)morphinan
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C24H25NO3
Molar mass 375.468 g·mol−1
3D model (JSmol)
  • c1ccc(cc1)CCN2CC[C@]34c5c6ccc(c5O[C@H]3[C@H](C=C[C@H]4[C@H]2C6)O)O
  • InChI=1S/C24H25NO3/c26-19-8-6-16-14-18-17-7-9-20(27)23-24(17,21(16)22(19)28-23)11-13-25(18)12-10-15-4-2-1-3-5-15/h1-9,17-18,20,23,26-27H,10-14H2/t17-,18+,20-,23-,24-/m0/s1
  • Key:BXKJGGVENHTVBF-JFDOVZFRSA-N
  (verify)

N-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl. It is around eight to fourteen times more potent than morphine as a result of this modification, in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as antagonists. 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 μ-opioid receptor cleft, analogous to the binding of the phenethyl group on fentanyl.

See also


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