3024 Dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is a key dipolar aprotic solvent. It is less toxic than other members of this class: dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA. Dimethyl sulfoxide is the chemical compound (CH3)2SO. This colorless liquid is an important dipolar aprotic solvent. It is readily miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, allowing the handler to taste it. Some describe it as an oyster-like taste, others claim it tastes like garlic. DMSO is also employed as a rinsing agent in the electronics industry and, in its deuterated form (DMSO-d6), is a useful solvent in NMR due to its ability to dissolve a wide range of chemical compounds and its minimal interference with the sample signals. 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. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cell, which are often frozen in a mixture of 10% DMSO and 90% fetal calf serum. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cell. Dimethyl sulfoxide is a by-product of wood pulping. One of the leading suppliers of DMSO is the Gaylord company in the USA. DMSO is frequently used as solvent in a number of chemical reactions. In particular it is an excellent reaction solvent for SN2 alkylations: it is possible to alkylate indoles with very high yields using potassium hydroxide as the base and a similar reaction also occurs with phenols. DMSO can be reacted with methyl iodide to form a sulfoxonium ion which can be reacted with sodium hydride to form a sulfur ylide. The methyl groups of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the resultant anions by the sulfoxide group. 67-68-5 679 C2H6OS 78.013940 18.5°C 63 1E+006 mg/L Topical ; parenteral(intravesical). Readily and rapidly absorbed following administration by all routes and distributed throughout the body. The mechanism of dimethyl sulfoxide's actions is not well understood. Dimethyl sulfoxide has demonstrated antioxidant activity in certain biological settings. For example, the cardiovascular protective effect of dimethyl sulfoxide in copper-deficient rats is thought to occur by an antioxidant mechanism. It is also thought that dimethyl sulfoxide's possible anti-inflammatory activity is due to antioxidant action. 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. Route of Elimination: Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces. LD50: >10 gm/kg (Oral, Dog) (A308) No indication of carcinogenicity to humans (not listed by IARC). DMSO is an important polar aprotic solvent. 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.[Wikipedia] Taking DMSO internally is reported to cause a fish- or oyster-like taste or odor in the mouth, likely due to the sulfoxide metabolites of DMSO. [Wikipedia] In case of accidental oral ingestion, specifc measures should be taken to induce emesis. Additional measures which may be considered are gastric lavage, activated charcoal and force diuresis. (L1712) 2009-07-21T20:28:21Z 2026-05-14T16:57:46Z Dimethyl_sulfoxide C11143 28262 DMSO Dimethyl sulfoxide DB01093 DMS 1711 true CS(C)=O C2H6OS InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 IAZDPXIOMUYVGZ-UHFFFAOYSA-N 78.133 78.013935504 Exogenous Liquid -1.35 HMDB02151 CHEMBL504 659 <p>Zhi Guo, Indra Prakash, &#8220;Synthesis and purification of 3,3-dimethylbutyraldehyde via oxidation of 1-chloro-3,3-dimethylbutane with dimethyl sulfoxide.&#8221; U.S. Patent US5905175, issued October, 1990.</p> CHEM002343 DTXSID2021735 NS00001957 methanesulfinylmethane 17.07 20.7254 7.907572341408355 0 1 0 -7.980512777159161 0 0 -1.09 -0.08 6.57e+01 g/l