LS-115509
Clinical data
ATC code
  • none
Identifiers
  • 4-ethoxy-4-(furan-2-yl)-3-methyl-1-(2-phenylethyl)piperidine
CAS Number
  • 94876-55-8
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H27NO2
Molar mass313.441 g·mol−1
3D model (JSmol)
  • CCOC1(CCN(CC1C)CCC2=CC=CC=C2)C3=CC=CO3
  • InChI=1S/C20H27NO2/c1-3-23-20(19-10-7-15-22-19)12-14-21(16-17(20)2)13-11-18-8-5-4-6-9-18/h4-10,15,17H,3,11-14,16H2,1-2H3
  • Key:INLMDDDTZIKNNI-UHFFFAOYSA-N

LS-115509 is an opioid analgesic related to the 4-phenylpiperidine family. It is comparable to drugs such as prodine and pheneridine, but is distinguished by the presence of an ether group and furan ring at the piperidine 4-position, which are not found in other drugs of this class. In animal studies, it has around 2-3x the potency of morphine depending on what assay is used. Like prodine, it has two stereocenters and four possible enantiomers, but the activity of these has not been tested separately.[1][2][3]

References

  1. ^ Casy AF, Beckett AH, Hall GH, Vallance DK (December 1961). "Chemistry and pharmacology of 4-alkoxy-piperidines related to reversed esters of pethidine". Journal of Medicinal and Pharmaceutical Chemistry. 4 (3): 535–51. doi:10.1021/jm50019a012. PMID 13877295.
  2. ^ Beckett AH, Casy AF (February 1965). "Analgesics and their antagonists: biochemical aspects and structure-activity relationships". Progress in Medicinal Chemistry. 4: 171–218. doi:10.1016/s0079-6468(08)70169-3. ISBN 9780444533234. PMID 5319798.
  3. ^ Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Orlando: Academic Press. p. 337. ISBN 978-0-12-443830-9.