3259. Dimethyl Sulfoxide

Nomenclature

CAS number: 67-68-5
1,1′-Sulfinylbismethane; methyl sulfoxide; DMSO; SQ-9453; Deltan (Berna); Dolicur (Schering AG); Domoso (Syntex); Kemsol (Carter Horner); Rheumabene (Merckle); Rimso-50 (Britannia).
C2H6OS; mol wt 78.13.
C 30.75%, H 7.74%, O 20.48%, S 41.04%.

Description and references

Dipolar, aprotic solvent. Attributed with a wide range of bioactivities including analgesic, anti-inflammatory and cryoprotective properties. Prepn: A. Saytzeff, Ann. 144, 148 (1867). Usually obtained as a by-product of paper manufacture: M. D. Robbins, Chem. Eng. 68, 100 (June 26, 1961). Toxicity data: W. Bartsch et al., Arzneim.-Forsch. 26, 1581 (1976). Review of properties and use in organic chemistry: D. Martin et al., Angew. Chem. Int. Ed. 6, 318-334 (1967). Reviews of pharmacology and toxicology: S. W. Jacob, D. C. Wood, Arzneim.-Forsch. 17, 1553-1560 (1967); N. A. David, Annu. Rev. Pharmacol. 12, 353-374 (1972); of clinical experience: Ann. N.Y. Acad. Sci. 411, entitled “Biological Actions and Medical Applications of Dimethyl Sulfoxide”, J. C. de la Torre, Ed. (1983) 402 pp; B. N. Swanson, Rev. Clin. Basic Pharmacol. 5, 1-33 (1985); of use in rheumatic disorders: J. M. Trice, R. S. Pinals, Semin. Arthritis Rheum. 15, 45-60 (1985). Review of veterinary uses: C. F. Brayton, Cornell Vet. 76, 61-90 (1986).

Chemical structure

Properties

Very hygroscopic liquid. Practically no odor or color. Slightly bitter with sweet after-taste. d420 1.100. mp 18.55°. bp760 189°; bp16 79.83°; bp12 72.5°. Flash pt, open cup: 203°F (95°C). nD20 1.4783. Viscosity (20°): 2.47 cP. Specific heat (25°): 0.4698 cal/g. Dielectric constant: 45. Sol in water, ethanol, acetone, ether, benzene, chloroform. LD50 orally in rats: 17.9 ml/kg (Bartsch).

Caution

Rapidly absorbed through skin and mucous membranes; enhances dermal absorption of many other chemicals. Repeated topical application may result in mild, erythamatous, scaling dermatitis. Corneal opacities have been produced in exptl animals. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 407.

Use

Solvent for many organic compds including fats, carbohydrates, dyes, resins, and polymers. In organic reactions. Determn of organic volatile impurities. As antifreeze or hydraulic fluid when mixed with water. To cryopreserve and store cultured cells.

Therapeutic Category

In treatment of interstitial cystitis and scleroderma.

Therapeutic Category (Veterinary)

Topically to reduce swelling due to trauma.