N-Phenethyl-14-ethoxymetopon

N-Phenethyl-14-ethoxymetopon is a drug that is a derivative of metopon. It is a potent analgesic, around 60 times stronger than morphine and produces significantly less constipation.[1]

N-Phenethyl-14-ethoxymetopon
Identifiers
IUPAC name
  • (5α)-14-Ethoxy-3-hydroxy-5-methyl-17-(2-phenylethyl)-4,5-epoxymorphinan-6-one
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H31NO4
Molar mass433.548 g·mol−1
3D model (JSmol)
SMILES
  • CCO[C@@]12CCC(=O)[C@]3([C@@]14CCN([C@@H]2CC5=C4C(=C(C=C5)O)O3)CCC6=CC=CC=C6)C
InChI
  • InChI=1S/C27H31NO4/c1-3-31-27-13-11-22(30)25(2)26(27)14-16-28(15-12-18-7-5-4-6-8-18)21(27)17-19-9-10-20(29)24(32-25)23(19)26/h4-10,21,29H,3,11-17H2,1-2H3/t21-,25+,26+,27-/m1/s1 N
  • Key:YNNFSTLAUJEYHI-NVSKSXHLSA-N N
 NY (what is this?)  (verify)

N-Phenethyl-14-ethoxymetopon acts as an agonist at both μ- and δ-opioid receptors, with a Ki of 0.16nM at μ and 3.14nM at δ.[2]

See also

References
  1. Ananthan S (March 2006). "Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics". The AAPS Journal. 8 (1): E118-25. doi:10.1208/aapsj080114. PMC 2751430. PMID 16584118.
  2. Lattanzi R, Spetea M, Schüllner F, Rief SB, Krassnig R, Negri L, Schmidhammer H (May 2005). "Synthesis and biological evaluation of 14-alkoxymorphinans. 22.(1) Influence of the 14-alkoxy group and the substitution in position 5 in 14-alkoxymorphinan-6-ones on in vitro and in vivo activities". Journal of Medicinal Chemistry. 48 (9): 3372–8. doi:10.1021/jm040894o. PMID 15857143.
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