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Dimethyl sulfoxide ( DMSO) is an organosulfur compound with the chemical formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar solvent aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a garlic-like taste in the mouth after DMSO is absorbed by skin.
In terms of chemical structure, the molecule has idealized Cs symmetry group. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a lone pair on the approximately tetrahedral sulfur atom.
This salt can be deprotonated with sodium hydride to form the sulfur ylide:
Deprotonation of DMSO requires strong bases like lithium diisopropylamide and sodium hydride. Stabilization of the resultant carbanion is provided by the S(O)R group. The sodium derivative of DMSO formed in this way is referred to as dimsyl sodium. It is a base, e.g., for the deprotonation of ketones to form sodium enolates, to form , and formamidinium salts to form . The dimsyl anion is a potent nucleophile.Mukulesh Mondal "Sodium methylsulfinylmethylide: A versatile reagent" Synlett 2005, vol. 17, 2697-2698.
In carbon tetrachloride solutions DMSO functions as a Lewis base with a variety of Lewis acids such as iodine, , trimethyltin chloride, metalloporphyrins, and the dimer . The donor properties are discussed in the ECW model. The relative donor strength of DMSO toward a series of acids, versus other Lewis bases, can be illustrated by ECW model. (2025). 9780470749579, John Wiley. ISBN 9780470749579 The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model.
Because of its high boiling point, , DMSO evaporates slowly at normal atmospheric pressure. Samples dissolved in DMSO cannot as easily be recovered compared to other solvents, as it is very difficult to remove all traces of DMSO by conventional rotary evaporation. One technique to fully recover samples is removal of the organic solvent by evaporation followed by addition of water (to dissolve DMSO) and freeze-drying to remove both DMSO and water. Reactions conducted in DMSO are often diluted with water to precipitate or phase-separate products. The relatively high freezing point of DMSO, , means that at, or just below, room temperature it is a solid.
In its deuterium form (Deuterated DMSO), it is a useful solvent for NMR spectroscopy, again due to its ability to dissolve a wide range of analytes, the simplicity of its own spectrum, and its suitability for high-temperature NMR spectroscopic studies. Disadvantages to the use of DMSO- d6 are its high viscosity, which broadens signals, and its hygroscopicity, which leads to an overwhelming H2O resonance in the 1H-NMR spectrum. It can be mixed with CDCl3 or CD2Cl2 for lower viscosity and melting points.
DMSO is used to dissolve test compounds in in vitro drug discovery and drug design bioassay programs, including high-throughput screening programs. This is because it is able to dissolve both polar and nonpolar compounds, can be used to maintain of test compounds (important when working with a large chemical library), is readily Miscibility with water and Growth medium, and has a high boiling point (this improves the accuracy of test compound concentrations by reducing room temperature evaporation). One limitation with DMSO is that it can affect cell line growth and viability, with low DMSO concentrations sometimes stimulating cell growth, and high DMSO concentrations sometimes inhibiting or killing cells.
DMSO is used as a vehicle in in vivo studies of test compounds. It has, for example, been employed as a co-solvent to assist absorption of the flavonol glycoside icariin in the nematode worm Caenorhabditis elegans. As with its use in in vitro studies, DMSO has some limitations in Model organism. Pleiotropic effects can occur and, if DMSO control groups are not carefully planned, then solvent effects can falsely be attributed to the prospective drug. For example, even a very low dose of DMSO has a powerful protective effect against paracetamol (acetaminophen)-induced liver injury in mice.
DMSO finds some use in manufacturing processes to produce microelectronic devices. It is widely used to strip photoresist in TFT-LCD 'flat panel' displays and advanced packaging applications (such as wafer-level packaging / solder bump patterning).
DMSO is also an excellent swelling agent for cellulosic fibres, and occasionally is utilised as solvent in some laboratory analyses respecting wood or fibre related quality control.
DMSO in a PCR is applicable for supercoiled plasmids (to relax before amplification) or DNA templates with high GC-content (to decrease thermostability). For example, 10% final concentration of DMSO in the PCR mixture with Phusion decreases primer annealing temperature (i.e., primer melting temperature) by .
It is well known as a reversible cell cycle arrester at phase G1 of human lymphoid cells.
DMSO may also be used as a cryoprotectant, added to cell media to reduce ice formation and thereby prevent cell death during the freezing process.
(2025). 9781588293770, Humana Press. ISBN 9781588293770
Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at or stored in liquid nitrogen safely.
In cell culture, DMSO is used to induce differentiation of P19 embryonic carcinoma cells into and skeletal muscle cells.
DMSO has been examined for the treatment of numerous conditions and ailments, but the U.S. Food and Drug Administration (FDA) has approved its use only for the symptomatic relief of patients with interstitial cystitis. A 1978 study concluded that DMSO brought significant relief to the majority of the 213 patients with inflammatory genitourinary disorders that were studied.
In 2009, the first to obtain FDA approval for topical DMSO usage was PENNSAID®, which contains diclofenac in a carrier with 45.5% DMSO
Each 1 mL of TDiclo contains 16.05 mg diclofenac sodium. TDiclo solution also contains 45.5% dimethyl sulfoxide (DMSO) vehicle, which can result in enhanced penetration of active drug through the skin.In interventional radiology, DMSO is used as a solvent for EVOH in the Onyx liquid embolic agent, which is used in embolization, the therapeutic occlusion of blood vessels.The most common adverse event reported was dry skin at the application site (25.3% of patients), followed by contact dermatitis (13.0%)
In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. Without it, up to 90% of frozen cells will become inactive. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cells, which are often frozen in a mixture of 10% DMSO, a freezing medium, and 30% fetal bovine serum. In the cryogenic freezing of heteroploid cell lines (MDCK, Vero cell, etc.) a mixture of 10% DMSO with 90% EMEM (70% EMEM + 30% fetal bovine serum + antibiotic mixture) is used. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cells.
DMSO is metabolized by disproportionation to dimethyl sulfide and dimethyl sulfone. It is subject to renal and pulmonary excretion. A possible side effect of DMSO is therefore elevated blood dimethyl sulfide, which may cause a blood borne halitosis symptom.
The use of DMSO as an alternative treatment for cancer is of particular concern, as it has been shown to interfere with a variety of chemotherapy drugs, including cisplatin, carboplatin, and oxaliplatin. There is insufficient evidence to support the hypothesis that DMSO has any effect, and most sources agree that its history of side effects when tested warrants caution when using it as a dietary supplement, for which it is marketed heavily with the usual disclaimer. DMSO is an ingredient in some products listed by the U.S. FDA as fake cancer cures and the FDA has had a running battle with distributors. One such distributor is Mildred Miller, who promoted DMSO for a variety of disorders and was consequently convicted of Medicare fraud.
DMSO can cause contaminants, toxins, and medicines to be absorbed through the skin, which may cause unexpected effects. DMSO is thought to increase the effects of blood thinners, steroids, heart medicines, sedatives, and other drugs. In some cases this could be harmful or dangerous.
Because DMSO easily penetrates the skin, substances dissolved in DMSO may quickly be absorbed. Glove selection is important when working with DMSO. Butyl rubber, fluoroelastomer, neoprene, or thick (15mil / 0.4millimetre) latex gloves are recommended. Rubber Chemical Resistance Chart Nitrile rubber gloves, which are very commonly used in chemical laboratories, may protect from brief contact but have been found to degrade rapidly with exposure to DMSO.
Considering its wide use, especially for cryopreservation and in vitro assays, we evaluated biological effect of DMSO using these technological innovations. We exposed 3D cardiac and hepatic microtissues to medium with or without 0.1% DMSO and analyzed the transcriptome, proteome and DNA methylation profiles. In both tissue types, transcriptome analysis detected >2000 differentially expressed genes affecting similar biological processes, thereby indicating consistent cross-organ actions of DMSO.There are transcriptional, translational and Epigenetics changes caused by low concentration DMSO, despite the lack of acute toxicity.
This is more of a concern for molecular biology experiments, because human body react transcriptionally to exogenic substances which can be totally normal and benign. For comparison, ethanol produces transcriptional changes that cause metabolic disorder.
On September 9, 1965, The Wall Street Journal reported that a manufacturer of the chemical warned that the death of an Irish woman after undergoing DMSO treatment for a sprained wrist may have been due to the treatment, although no autopsy was done, nor was a causal relationship established. Clinical research using DMSO was halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972. fda.gov In 1978, the US FDA approved DMSO for treating interstitial cystitis. In 1980, the US Congress held hearings on claims that the FDA was slow in approving DMSO for other medical uses. In 2007, the US FDA granted "fast track" designation on clinical studies of DMSO's use in reducing brain tissue swelling following traumatic brain injury.
DMSO exposure to developing mouse brains can produce brain degeneration. This neurotoxicity could be detected at doses as low as 0.3mL/kg, a level exceeded in children exposed to DMSO during bone marrow transplant.
DMSO can decompose at the boiling temperature of 189 °C at normal pressure, possibly leading to an explosion. The decomposition is catalyzed by acids and bases and therefore can be relevant at even lower temperatures. A strong to explosive reaction also takes place in combination with halogen compounds, metal nitrides, metal perchlorates, sodium hydride, periodic acid and fluorinating agents. (2000). 9783609730905, Verlagsgruppe Hüthig Jehle Rehm. ISBN 9783609730905 CD-ROM:
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