IC-26

Last updated

IC-26
IC-26 structure.svg
Identifiers
  • 4-ethylsulfonyl-N,N-dimethyl-4,4-diphenylbutan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H27NO2S
Molar mass 345.50 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IC-26 [1] (WIN 1161-3,Methiodone) [2] is an analogue of the opioid analgesic methadone, where the carbonyl group has been replaced by the bioisosteric sulfone group.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, [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.

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. ↑ USpatent 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.


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