Sulfonmethane

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IUPAC_name = 2,2-bis(ethylsulfonyl)propane

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CAS_number = 115-24-2
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PubChem = 8262
C=7 | H=16 | O=4 | S=2
molecular_weight = 228.3295 g/mol
smiles = CCS(=O)(=O)C(C)(C)S(=O)(=O)CC
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legal_US = Schedule III
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Sulfonmethane (Sulfonomethane, Sulfonal, Acetone diethyl sulfone) is a chemical compound formerly used as a hypnotic drug, but now superseded by newer and safer sedatives. [ [http://www.thefreedictionary.com/sulfonmethane American Heritage Dictionary] ] Its appearance is either in colorless crystalline or powdered form. In United States, it is scheduled as a Schedule III drug in the Controlled Substance Act. [ [http://www.usdoj.gov/dea/pubs/scheduling.html DEA Scheduling] ]

Effects

It produces lengthened sleep in functional nervous insomnia, and is also useful in insanity, being given with mucilage of acacia or in hot liquids, owing to its insolubility, or in large capsules. Its hypnotic power is not equal to that of chloral, but as it is not a depressant to the heart or respiration it can be used when morphine or chloral are contra-indicated. It is, however, very uncertain in its action, often failing to produce sleep when taken at bedtime, but producing drowsiness and sleep the following day. The drowsiness the next day following a medicinal dose can be avoided by a saline laxative the morning after its administration. It is unwise to use it continuously for more than a few days at a time, as it tends to produce the sulfonal habit, which is attended by marked toxic effects, disturbances of digestion, giddiness, staggering gait and even paralysis of the lower extremities. These effects are accompanied by skin eruptions, and the urine becomes of a dark red color (hematoporphinuria). Sulfonal is cumulative in its effects. Many fatal cases of sulfonal poisoning are on record, both from chronic poisoning and from a single large dose.

Chemistry

Sulfonal is prepared by condensing acetone with ethyl mercaptan in the presence of hydrochloric acid, the mercaptol (CH₃)₂C(SC₂H₅)₂ formed being subsequently oxidized by potassium permanganate. It is also formed by the action of alcoholic potash and methyl iodide on ethylidene diethyl sulfine, CH₃•CH(SO₂C₂H₅)₂ (which is formed by the oxidation of dithioacetal with potassium permanganate). It crystallizes in prisms melting at 125 C, which are practically insoluble in cold water, but dissolve in 15 parts of hot and also in alcohol and ether.

Related Compounds

Trional (CH₃)(C₂H₅)C(SO₂C₂H₅)₂, and tetronal, (C₂H₅)₂C(SO₂C₂H₅)₂, are also obsolete hypnotics. They are faster in action than sulfonal, and trional does not disorder the digestion.

References