Dimethyl sulfoxide
From Wikipedia, the free encyclopedia
| Dimethyl sulfoxide | |
|---|---|
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| General | |
| Systematic name | Dimethyl sulfoxide |
| Other names | Methyl sulfoxide methylsulfinylmethane DMSO |
| Molecular formula | C2H6OS |
| SMILES | CS(C)=O |
| Molar mass | 78.13 g/mol |
| Appearance | Clear, colorless liquid |
| CAS number | [67-68-5] |
| Properties | |
| Density and phase | 1.1004 g/cm3, liquid |
| Solubility in water | Miscible |
| Solubility in ethanol, benzene, chloroform |
Miscible |
| Melting point | 18.5 °C (292 K) |
| Boiling point | 189 °C (462 K) |
| Viscosity | 1.996 cP at 20 °C |
| Acid dissociation constant | 35 (in DMSO) |
| Structure | |
| Dipole moment | 3.96 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Irritant (Xi) |
| NFPA 704 |
1
1
0
|
| R-phrases | R36/37/38 |
| S-phrases | S26, S37/39 |
| Flash point | 95 °C |
| RTECS number | PV6210000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related sulfoxides | diethyl sulfoxide |
| Related compounds | dimethyl sulfide, dimethyl sulfone, acetone |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Dimethyl sulfoxide (DMSO) is the chemical compound (CH3)2SO. This colorless liquid is an important polar 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.
Contents |
[edit] Production
Dimethyl sulfoxide is a by-product of wood pulping. One of the leading suppliers of DMSO is the Gaylord Chemical Corporation in the USA.
[edit] Applications
[edit] Solvent
DMSO is a very important polar aprotic solvent. It is less toxic than other members of this class such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA.
DMSO is frequently used as solvent for chemical reactions. Its polarity accelerates reactions with charged transition states, such as SN2 alkylations of indoles and phenols.. Because DMSO is only weakly acidic, it tolerates relatively strong bases.
In its deuterated form (DMSO-d6), is a useful solvent in NMR due to its ability to dissolve a wide range of analytes and its own simple spectrum. Disadvantages to the use of DMSO-d6 are its high viscosity, which broadens signals, and high boiling point, which interferes with sample recovery from the NMR solvent.
DMSO is an effective paint stripper, being much safer than many of the other such as nitromethane and dichloromethane.
[edit] Reactions
DMSO reacts with methyl iodide to form a sulfoxonium ion which can be deprotonated 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 carbanion by the S(O)R group.
In organic synthesis, DMSO is used as an oxidant,[1], such as the Pfitzner-Moffatt oxidation and the Swern oxidation.[2]
Products of ozonolysis, trioxolanes, are quenched with dimethyl sulfide to produce aldehydes and DMSO.
[edit] Biology
DMSO is used in the PCR reaction to inhibit secondary structures in the DNA template or the DNA primers. It is added to the PCR mix before reacting, where it interferes with the self-complementarity of the DNA, allowing otherwise troublesome reactions to occur. However, use of DMSO in PCR increases the mutation rate.
[edit] Medicine
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 cells, 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 cells.
Use of DMSO in medicine dates from around 1963, when a University of Oregon Medical School team, headed by Stanley Jacob, discovered it could penetrate the skin and other membranes without damaging them and could carry other compounds into a biological system. Some people report an onion- or garlic-like taste after touching DMSO. This is likely due to catabolic processes which reduce DMSO to dimethyl sulfide. In the medical field DMSO is predominantly used as a topical analgesic, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory and an antioxidant. It has been examined for the treatment of numerous conditions and ailments. The Food and Drug Administration (FDA) has approved DMSO usage only for the palliative treatment of interstitial cystitis. Also, DMSO is commonly used in the veterinary field as a liniment for horses.
Because DMSO increases the rate of absorption of some compounds through organic tissues including skin, it can be used as a drug delivery system.
Dimethyl sulfoxide dissolves a variety of organic substances, including carbohydrates, polymers, peptides, as well as many inorganic salts and gases. Loading levels of 50-60 wt. % are often observed vs 10-20 wt. % with typical solvents. For this reason DMSO plays a role in sample management and High-throughput screening operations in drug design [3].
[edit] Safety
Because DMSO easily penetrates the skin, substances dissolved in DMSO may be quickly absorbed. For instance, a solution of sodium cyanide in DMSO can cause cyanide poisoning through skin contact. DMSO by itself has low toxicity.[4] Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides. Recently, it was found that DMSO waste disposal into sewers can cause environmental odor problems in cities: Waste water bacteria transform DMSO under hypoxic (anoxic) conditions into dimethyl sulfide (DMS) that is slightly toxic and has a strong disagreeable odor, similar to rotten cabbage. [5].
[edit] See also
- Methylsulfonylmethane (MSM), a related chemical often used as a dietary supplement
[edit] References
- ^ Epstein W.W., Sweat F.W. (1967). "Dimethyl Sulfoxide Oxidations". Chemical Reviews 67: 247-260. DOI:10.1021/cr60247a001.
- ^ Tidwell, T.T. (1990). "Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update". Synthesis: 857-870. DOI:10.1055/s-1990-27036.
- ^ Balakin, K. V., Savchuk, N. P., Tetko I. V. (2006). "In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions)". Current Medicinal Chemistry 13 (2). DOI:10.2174/092986706775197917.
- ^ Vignes, Robert (August 2000). Dimethyl Sulfoxide (DMSO): A "new" clean, unique, superior solvent, American Chemical Society Annual Meeting
- ^ Glindemann, D., Novak, J., Witherspoon, J. (2006). "Dimethyl Sulfoxide (DMSO) Waste Residues and Municipal Waste Water Odor by Dimethyl Sulfide (DMS): the North-East WPCP Plant of Philadelphia.". Environmental Science and Technology 40 (1): 202-207. DOI:S0013-936X(05)01312-X 10.1021/es051312a S0013-936X(05)01312-X.
[edit] External links
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