IC-26

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);
PubChem CID	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IC-26¹ (WIN 1161-3, Methiodone)² is an analogue of the opioid analgesic methadone, where the carbonyl group has been replaced by the bioisosteric sulfone group.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,³⁴ 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 dependence⁵ it was never placed under international control as an illegal drug.

References

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 from the original on 2013-07-21. Retrieved 2017-09-09.
Wolbach AB, Fraser HF (1963). "Addiction Liability of I-C-26". Bulletin on Narcotics. 1963 (1). UNODC: 25–28.

[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.

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Identifiers

IUPAC name 4-ethylsulfonyl-N,N-dimethyl-4,4-diphenylbutan-2-amine
CAS Number	114538-73-7^Y 60662-79-5 (hydrochloride)
PubChem CID	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)

See also

References