IC-26

IC-26
Identifiers
  • 4-ethylsulfonyl-N,N-dimethyl-4,4-diphenylbutan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H27NO2S
Molar mass345.50 g·mol−1
3D model (JSmol)
  • CCS(=O)(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
  • 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IC-26 (WIN 1161-3, Methiodone) is an analogue of the opioid analgesic methadone, where the carbonyl group has been replaced by the bioisosteric sulfone group.

Human and animal studies suggest that IC-26 is around the same potency as methadone, 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 it was never placed under international control as an illegal drug. It has appeared as a designer drug, first reported in 2025, along with the corresponding piperidine analogue DPP-26.

See also

References

  1. ↑ 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.
  2. ↑ 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
  3. ↑ Lednicer, D. (1982). Central Analgetics. Wiley. p. 194. ISBN 0-471-08314-3.
  4. ↑ Janssen PA (1960). "XVIII Sulphones". Diphenylpropylamines. Synthetic Analgesics. Vol. 1. Pergamon Press. pp. 160–163. LCCN 59-13814. Archived from the original on 2013-07-21. Retrieved 2017-09-09.
  5. ↑ Wolbach AB, Fraser HF (1963). "Addiction Liability of I-C-26". Bulletin on Narcotics. 1963 (1). UNODC: 25–28.
  6. ↑ Smolders EJ, Klein T, Vries-Koenjer MLM, van de Velde B, van Berlo-van de Laar IRF, Vandeputte MM, Valkenburg AJ, Ruiz C, Stove CP, Maring JG, den Besten-Bertholee D, Roosendaal J. Methiodone (IC-26) a case series: an old, but novel, opioid substance causing severe toxicity. Arch Toxicol. 2026 Oct 31. doi:10.1007/s00204-026-04624-4 PMID 42965604