N-Phenethylnordesomorphine

N-Phenethylnordesomorphine is an opiate analgesic drug derived from desomorphine by replacing the N-methyl group with β-phenethyl. Since desomorphine is already around eight times more potent than morphine, the additional boost in binding affinity produced by using the larger phenethyl group makes N-phenethylnordesomorphine a highly potent analgesic drug, some 85x more potent than morphine,[1] and a similar strength to the closely related morphinan derivative phenomorphan.

N-Phenethylnordesomorphine
Identifiers
IUPAC name
  • 3-hydroxy-4,5α-epoxy-17-(2-phenylethyl)morphinan
PubChem CID
ChemSpider
Chemical and physical data
FormulaC24H27NO2
Molar mass361.485 g·mol−1
3D model (JSmol)
SMILES
  • [H][C@@]12[C@]3(CCN4CCC5=CC=CC=C5)C6=C(O2)C(O)=CC=C6C[C@@H]4[C@]3([H])CCC1
InChI
  • InChI=1S/C24H27NO2/c26-20-10-9-17-15-19-18-7-4-8-21-24(18,22(17)23(20)27-21)12-14-25(19)13-11-16-5-2-1-3-6-16/h1-3,5-6,9-10,18-19,21,26H,4,7-8,11-15H2/t18-,19+,21-,24+/m0/s1 Y
  • Key:JZVQXSYNZPVRTQ-FPRSRYDQSA-N Y
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See also

References
  1. Casy AF, Parfitt RY (1986). Opioid analgesics, chemistry and receptors. New York: Plenum Press. pp. 37–38. ISBN 978-0-306-42130-3.


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