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LS-115509

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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^Y
PubChemCID	3024404
ChemSpider	2290335
UNII	XG2JQX2JDJ
CompTox Dashboard(EPA)	DTXSID50915236
Chemical and physical data
Formula	C₂₀H₂₇NO₂
Molar mass	313.441 g·mol⁻¹
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 anopioid analgesic related to the4-phenylpiperidine family. It is comparable to drugs such asprodine andpheneridine, but is distinguished by the presence of anether group andfuran 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 ofmorphine depending on what assay is used. Like prodine, it has two stereocenters and four possibleenantiomers, but the activity of these has not been tested separately.^[1]^[2]^[3]

References

[edit]

^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.