IC-26

IC-26[1] (WIN 1161-3, Methiodone)[2] is an analogue of the opioid analgesic methadone, where the carbonyl group has been replaced by the bioisosteric sulfone group.

IC-26
Identifiers
IUPAC name
  • 4-ethylsulfonyl-N,N-dimethyl-4,4-diphenylbutan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H27NO2S
Molar mass345.50 g·mol−1
3D model (JSmol)
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)

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 methadone 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. 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. 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.
  5. Wolbach AB, Fraser HF (1963). "Addiction Liability of I-C-26". Bulletin on Narcotics. UNODC. 1963 (1): 25–28.
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