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IC-26

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From Wikipedia, the free encyclopedia

Chemical compound

For other uses, seeIC 26 (disambiguation).

Pharmaceutical compound

IC-26
Identifiers

IUPAC name 4-ethylsulfonyl-N,N-dimethyl-4,4-diphenylbutan-2-amine
CAS Number	114538-73-7^Y 60662-79-5 (hydrochloride)
PubChemCID	113832
ChemSpider	102014
UNII	ZSY3T8J4AQ
CompTox Dashboard(EPA)	DTXSID401018280
Chemical and physical data
Formula	C₂₀H₂₇NO₂S
Molar mass	345.50 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCS(=O)(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
InChI InChI=1S/C20H27NO2S/c1-5-24(22,23)20(16-17(2)21(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3 Key:NLPGJSPLDNDKKZ-UHFFFAOYSA-N
(verify)

IC-26^[1] (WIN 1161-3,Methiodone)^[2] is ananalogue of the opioid analgesicmethadone, where thecarbonyl group has been replaced by thebioisosteric sulfone group.

Human and animal studies suggest that IC-26 is around the same potency as methadone,^[3]^[4] although other studies have found its activity to be inconsistent between different patients, with consistent opioid activity only being seen at a dose several times that of methadone. IC-26 was assessed for its abuse potential, but despite being found to have similar potential to morphine for development of dependence^[5] it was never placed under international control as an illegal drug.

References

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^Tullar BF, Wetterau W, Archer S (November 1948). "The Resolution of Ethyl 1,1-Diphenyl-3-dimethylaminobutyl Sulfone".Journal of the American Chemical Society.70 (11):3959–3960.Bibcode:1948JAChS..70R3959T.doi:10.1021/ja01191a532.PMID 18207952.
^US patent 2618640, Archer S, Suter CM, Tullar BF, "Certain amino hydrocarbon sulfones and process of preparation", issued 1952-11-18, assigned to Sterling Drug
^Lednicer, D. (1982).Central Analgetics. Wiley. p. 194.ISBN 0-471-08314-3.
^Janssen PA (1960)."XVIII Sulphones".Diphenylpropylamines. Synthetic Analgesics. Vol. 1. Pergamon Press. pp. 160–163.LCCN 59-13814. Archived fromthe original on 2013-07-21. Retrieved2017-09-09.
^Wolbach AB, Fraser HF (1963)."Addiction Liability of I-C-26".Bulletin on Narcotics.1963 (1). UNODC:25–28.