LS-115509 - Misplaced Pages

Chemical compound Pharmaceutical compound

LS-115509
Clinical data

ATC code	none
Identifiers
IUPAC name 4-ethoxy-4-(furan-2-yl)-3-methyl-1-(2-phenylethyl)piperidine
CAS Number	94876-55-8
PubChem CID	3024404
ChemSpider	2290335
UNII	XG2JQX2JDJ
CompTox Dashboard (EPA)	DTXSID50915236
Chemical and physical data
Formula	C₂₀H₂₇NO₂
Molar mass	313.441 g·mol
3D model (JSmol)	Interactive image
SMILES CCOC1(CCN(CC1C)CCC2=CC=CC=C2)C3=CC=CO3
InChI 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.

References

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.
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.
Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Orlando: Academic Press. p. 337. ISBN 978-0-12-443830-9.