Dimethyl sulfoxide

Absorption

Readily and rapidly absorbed following administration by all routes and distributed throughout the body.

Toxicity

The oral LD50 of dimethyl sulfoxide in the dog is greater than 10 gm/kg. It is improbable that this dosage level could be obtained with intravesical instillation of dimethyl sulfoxide in the patient.

Description

First synthesized in 1866 by Alexander Zaytsev in the Russian Empire, dimethyl sulfoxide is an organosulfur compound. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water.

Description

Dimethyl sulfoxide (DMSO) is a widely used solvent that is miscible with water and a wide range of organic solvents. It goes by several names, including methyl sulfoxide, sulfinylbismethane, and dozens of trade names.
DMSO was first discovered in the late 19th century as a byproduct of the kraft process for making paper from wood pulp. About the same time, Russian chemist Alexander Zaytsev synthesized it by oxidizing dimethyl sulfide, another kraft process byproduct. Zaytsev’s synthesis is the basis for the manufacturing process still used today.
DMSO is a laboratory and industrial solvent for many gases, synthetic fibers, paint, hydrocarbons, salts, and natural products. Because it is aprotic, relatively inert, nontoxic, and stable at high temperatures, it is a frequently used solvent for chemical reactions. Its deuterated form is an ideal solvent for NMR spectroscopy.
In the 1960s, scientists observed that DMSO penetrates human skin with little effect on tissues; and the solvent was tested as a way for medicines to be carried into the body as an alternative to oral formulations or injectables. Since then, DMSO has been used in some transdermal drug delivery systems (i.e., patches). In 1978 the US Food and Drug Administration approved it for use for the symptomatic relief of chronic interstitial cystitis (bladder pain syndrome)—the only FDA approval for DMSO as an actual medication.
As one might expect for the 1960s, DMSO was tried as an alternative drug for inflammation relief and as a solvent for introducing illicit drugs such as cocaine into the body. It was also wrongly touted as a cancer cure. In 1965, FDA put the kibosh on much of this activity by banning clinical trials with DMSO because the compound altered the refractive index of eye lenses of laboratory animals. The ban was lifted in 1980 after the intense interest in the substance abated.
Researchers continue to look at DMSO as a possible medical treatment. In 2016, Gerald Krystal and colleagues at the British Columbia Cancer Agency (Vancouver), the University of British Columbia (Vancouver), and Vancouver General Hospital reported that DMSO represses inflammatory cytokine production from human blood cells and thus reduces autoimmune arthritis. The authors also examined whether DMSO has any anticancer activity; they concluded that they could not confirm that it does.

Description

Dimethyl sulfoxide (DMSO) is a polar aprotic solvent that can dissolve a wide range of organic compounds. The high dissolving power of DMSO makes deuterated DMSO (DMSO-d6) a common solvent for NMR. One of the major drawbacks of DMSO is the difficulty of removal after a reaction. Its high boiling point (189 C) makes removal by rotovap very difficult. DMSO is also used as a reagent in a variety of different reactions.

The Uses of Dimethyl sulfoxide

Dimethyl sulfoxide (1-10%) has been shown to accelerate strand renaturation and is believed to give the nucleic acid thermal stability against depurination. As a PCR cosolvent, DMSO may help improve yields, especially in long PCR.

The Uses of Dimethyl sulfoxide

To a stirred solution of (COCl)2 (0.49 mL, 5.5 mmol) in DCM (12 mL) was slowly added DMSO (0.79 mL, 11.0 mmol) at -78 C. The resulting mixture was stirred at -78 C for 30 min. To the mixture was slowly added a solution of the SM (845 mg, 5.0 mmol) in DCM (10 mL) over 10 min, followed by the dropwise addition of TEA (3.1 mL, 22.5 mmol). The reaction mixture was slowly allowed to warm to RT. The mixture was stirred 1 h at RT, after which time it was quenched with H2O (10 mL). The mixture was extracted with DCM (3 x 20 mL). The combined organics were washed with 1M HCl (10 mL), sat aq Na2CO3, brine, dried (Na2SO4), and concentrated. The resulting material was purified by silica gel column chromatography (2:1 PE/EtOAc) to provide the product as an off-white solid. [600 mg, 72%]

Background

A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during cryopreservation. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.

Indications

For the symptomatic relief of patients with interstitial cystitis.

What are the applications of Application

DMSO, Sterile Filtered is a versatile highly polar organic solvent

What are the applications of Application

Dimethyl Sulfoxide (DMSO), Cell Culture reagent is a polar, aprotic organic solvent ideal for cryopreservation

What are the applications of Application

Dimethyl Sulfoxide (DMSO) is a versatile, highly polar, aprotic organic solvent used in chemical and polymerase chain reactions, and as a cryoprotectant vitrification agent.

Pharmacokinetics

Dimethyl Sulfoxide may have anti-inflammatory, antioxidant and analgesic activities. Dimethyl Sulfoxide also readily penetrates cellular membranes. The membrane-penetrating ability of dimethyl sulfoxide may enhance diffusion of other substances through the skin. For this reason, mixtures of idoxuridine and dimethyl sulfoxide have been used for topical treatment of herpes zoster in the United Kingdom.

Metabolism

Dimethyl sulfoxide is metabolized in man by oxidation to dimethyl sulfone or by reduction in dimethyl sulfide. Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.