Dimethyl sulfoxide
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225373945
2008-07-13T10:14:04Z
Closedmouth
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Reverted edits by [[Special:Contributions/98.220.69.15|98.220.69.15]] to last version by Ageekgal (using [[WP:HG|Huggle]])
{{Chembox new
| Name = Dimethyl sulfoxide
| ImageFile = DMSO-2D-dimensions.png
| ImageSize = 150px
| ImageName = Dimethyl sulfoxide
| ImageFileL1 = DMSO-3D-vdW.png
| ImageSizeL1 = 100px
| ImageNameL1 = 3D model of DMSO
| ImageFileR1 = DMSO-elpot.png
| ImageSizeR1 = 100px
| ImageNameR1 = 3D electric potential surface of DMSO
| IUPACName = Dimethyl sulfoxide
| OtherNames = Methyl sulfoxide<br />methylsulfinylmethane<br />DMSO
| Section1 = {{Chembox Identifiers
| SMILES = CS(C)=O
| CASNo = 67-68-5
| RTECS = PV6210000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>6</sub>OS
| MolarMass = 78.13 g/mol
| Appearance = Clear, colorless liquid
| Density = 1.1004 g/cm<sup>3</sup>, liquid
| Solubility = Miscible
| MeltingPt = 18.5 °C (292 K)
| BoilingPt = 189 °C (462 K)
| Viscosity = 1.996 [[Poise|cP]] at 20 °C
| RefractIndex = 1.479<br /> [[Dielectric constant|ε<sub>r</sub>]] = 48
| pKa = 35
}}
| Section3 = {{Chembox Structure
| Dipole = 3.96 [[Debye|D]]
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/ME/methyl_sulfoxide.html DMSO Material Safety Data Sheet]
| MainHazards = Irritant (Xi), Flammable (F)
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R =
| RPhrases = {{R36/37/38}}
| SPhrases = {{S26}}, {{S37/39}}
| FlashPt = 89 °C
}}
| Section8 = {{Chembox Related
| Function = [[sulfoxide]]s
| OtherFunctn = [[diethyl sulfoxide]]
| OtherCpds = [[sodium methylsulfinylmethylide]],<br />[[dimethyl sulfide]],<br /> [[methylsulfonylmethane|dimethyl sulfone]],<br /> [[acetone]]
}}
}}
'''Dimethyl sulfoxide''' (DMSO) is the [[chemical compound]] with the [[chemical formula|formula]] (CH<sub>3</sub>)<sub>2</sub>SO. This colorless liquid is an important [[polar solvent|polar]] [[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 distinctive property of penetrating the skin very readily, allowing the handler to taste it. Its taste has been described as [[oyster]]- or [[garlic]]-like.
==Production==
Dimethyl sulfoxide is a by-product of [[wood pulp]]ing. A supplier of DMSO is the [[Gaylord Chemical Corporation]] in the [[USA]].
==Applications==
===Solvent===
[[Image:Vacuum distillation of DMSO at 70C.jpg|left|thumb|DMSO is usually not evaporated; when necessary it is distilled from the reaction mixture under high vacuum.]]
DMSO is an important [[polar aprotic solvent]]. It is less toxic than other members of this class such as [[dimethylformamide]], [[dimethylacetamide]], [[Methylpyrrolidone|''N''-methyl-2-pyrrolidone]], [[Hexamethylphosphoramide|HMPA]]. Because of its excellent solvating power, DMSO is frequently used as [[solvent]] for chemical reactions involving salts, most notably [[Finkelstein reaction]]s and other [[nucleophilic substitution]]s. Because DMSO is only weakly acidic, it tolerates relatively strong bases, and as such has been extensively used in the study and chemistry of [[carbanion]]s. The work of the Bordwell group has provided a valuable set of non-aqueous [[pKa]] values (C-H, O-H, S-H and N-H acidities) for hundreds of organic compounds in DMSO.<ref name=Bordwell>"Equilibrium acidities in dimethyl sulfoxide solution," F. G. Bordwell [[Acc. Chem. Res.]] '''1988''', ''21'', 456, 463; {{DOI|10.1021/ar00156a004}} [http://www.chem.wisc.edu/areas/reich/pkatable/ Bordwell pKa Table in DMSO]</ref>
A practical problem with DMSO as a solvent is its high boiling point, thus its solutions are not typically evaporated. Instead, reactions conducted in DMSO are often diluted with water to precipitate or phase separate organic products. DMSO is an effective [[paint stripper]], being safer than many of the others such as [[nitromethane]] and [[dichloromethane]]. The relatively high freezing point of DMSO means that at, or just below, room temperature it is a solid, which can limit its utility in some chemical processes (e.g. crystallisation with cooling).
In its [[deuterium|deuterated]] form, i.e. [[Deuterated DMSO|DMSO-d<sub>6</sub>]], it is a useful but expensive solvent for [[Nuclear magnetic resonance|NMR]] spectroscopy, again due to its ability to dissolve a wide range of analytes, its own simple spectrum, and its suitability for high-temperature NMR spectroscopic studies. Disadvantages to the use of DMSO-d<sub>6</sub> are its high viscosity, which broadens signals, and high boiling point, which interferes with sample recovery from the NMR solvent. Often it is used with [[deuterated chloroform|deuterochloroform]], because the 1:1 mixture has a lower viscosity.
===Reactions===
The sulfur center in DMSO is nucleophilic toward soft electrophiles and the oxygen is nucleophilic toward hard electrophiles. The methyl groups of DMSO are somewhat acidic in character (p''K''<sub>a</sub>=35) due to the stabilization of the resultant [[carbanion]] by the S(O)R group, and so are deprotonated with strong bases like [[lithium diisopropylamide]] and [[sodium hydride]]. The sodium salt of DMSO formed in this way (sometimes referred to as "dimsyl sodium") is a useful base, e.g. it is often used for the [[deprotonation]] of [[ketones]] to form sodium [[enolates]], [[phosphonium salt]]s to form [[Wittig reagent]]s, and [[formamidinium]] salts to form [[diaminocarbene]]s.
DMSO reacts with [[methyl iodide]] to form a sulfoxonium salt [(CH<sub>3</sub>)<sub>3</sub>SO]I, which can be deprotonated with [[sodium]] [[hydride]] to form the [[sulfur]] [[ylide]]:
:(CH<sub>3</sub>)<sub>2</sub>SO + CH<sub>3</sub>I → [(CH<sub>3</sub>)<sub>3</sub>SO]I
:[(CH<sub>3</sub>)<sub>3</sub>SO]I + NaH → [(CH<sub>3</sub>)<sub>2</sub>CH<sub>2</sub>SO + NaI + H<sub>2</sub>
In [[organic synthesis]], DMSO is used as a mild oxidant,<ref>{{cite journal|author= Epstein W.W., Sweat F.W.|title=Dimethyl Sulfoxide Oxidations|journal= [[Chemical Reviews]]|year= 1967| volume= 67|pages= 247–260|doi=10.1021/cr60247a001}}</ref> such as the [[Pfitzner-Moffatt oxidation]] and the [[Swern oxidation]].<ref>{{cite journal | author= Tidwell, T.T. | title=Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update | journal= Synthesis | year= 1990 | volume = 1990 | pages=857–870 | doi=10.1055/s-1990-27036}}</ref>
Products of [[ozonolysis]], [[trioxolane]]s, are quenched with [[dimethyl sulfide]] to produce [[aldehyde]]s and DMSO.
===Biology===
DMSO is used in the [[PCR reaction]] to inhibit [[Polymerase chain reaction#Hairpins|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.<ref>{{Citation
| author = Chakrabarti R., Schutt C.E.
| year = 2001
| title = The enhancement of PCR amplification by low molecular-weight sulfones
| periodical = Gene
| volume = 274
| issue = 1-2
| pages = 293–298
| doi = 10.1016/S0378-1119(01)00621-7
| journal = Gene
}}</ref> However, use of DMSO in PCR increases the [[mutation]] rate.{{Fact|date=December 2007}}
DMSO also sees use as a [[cryoprotectant]], added to cell media in order to prevent the cells dying as they are frozen.{{Fact|date=December 2007}} Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at -20°C or stored in [[liquid nitrogen]] safely.
===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. Without it, up to 90 percent of frozen cells will become inactive. It is particularly important in the freezing and long-term storage of [[embryonic stem cells]] and [[hematopoietic stem cell]]s, which are often frozen in a mixture of 10% DMSO and 90% fetal calf [[blood plasma|serum]]. As part of an autologous [[bone marrow transplant]] the DMSO is re-infused along with the patient's own [[hematopoietic stem cell]]s.
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.
In a 1978 study at the [[Cleveland Clinic]] Foundation in [[Cleveland, Ohio]], researchers concluded that DMSO brought significant relief to the majority of the 213 patients with inflammatory [[genitourinary]] disorders that were studied.<ref>[http://www.dmso.org/articles/bladder/bladder1.htm Dimethyl Sulfoxide in Treatment of Inflammatory Genitourinary Disorders<!-- Bot generated title -->]</ref> They recommended [[DMSO]] for all inflammatory conditions not caused by infection or tumor in which symptoms were severe or patients failed to respond to conventional therapy.
Some people report an onion- or garlic-like taste after touching DMSO. ([[Onion]] and [[garlic]] also derive their stinginess from sulfoxides [[syn-propanethial-S-oxide]] and [[allicin]].) In the medical field DMSO is predominantly used as a topical [[analgesic]]<ref>{{cite web|author=Diagnose-me.com|title=Topical DMSO|url=http://www.diagnose-me.com/treat/T215027.html|date=2008-04-27|accessdate=2008-06-23}}</ref>, a vehicle for topical application of pharmaceuticals, as an [[anti-inflammatory]]<ref>{{cite web|author=Drugs.com|title=Nuvo announces further update on discussions with the FDA related to review of Pennsaid|url=http://www.drugs.com/nda/pennsaid_070307.html|date=2007-03-27|accessdate=2008-05-01}}</ref> and an [[antioxidant]]{{Fact|date=December 2007}}. 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 [[Biological tissue|tissues]] including [[skin]], it can be used as a drug delivery system.
Dimethyl sulfoxide dissolves a variety of organic substances, including [[carbohydrate]]s, [[polymer]]s, [[peptide]]s, 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.<ref>{{cite journal | author=Balakin, K. V., Savchuk, N. P., Tetko I. V. | journal=Current Medicinal Chemistry | year=2006 | volume= 13 | issue=2 | title=In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions) | doi=10.2174/092986706775197917 | pages=223}}</ref>
====History====
On September 9, 1965, the ''Wall Street Journal'' reported the death of an Irish woman after undergoing DMSO treatment for a sprained wrist<ref> Carley W. DMSO May Have Caused Death of Woman, Makers of 'Wonder' Drug Warn Doctors. Wall Street Journal. September 9, 1965:6.</ref> Clinical research using DMSO halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972.{{Fact|date=October 2007}} In 1978, the FDA approved DMSO for treating interstitial cystis. In 1980, Congress held hearings on claims that the FDA was slow in approving DMSO for other medical uses. In 2007, the FDA granted "fast track" designation on clinical studies of DMSO's use in reducing brain tissue swelling following traumatic brain injury.{{Fact|date=October 2007}}
==Safety==
MSDS recommends wearing safety glasses because DMSO can cause chronic damage to the eyes.<ref>{{cite web | publisher = [[Oxford University]] | title = Safety data for methyl sulfoxide | url = http://ptcl.chem.ox.ac.uk/MSDS/ME/methyl_sulfoxide.html}}</ref> Glove selection is important when working with DMSO. Thick rubber gloves are recommended. [[Nitrile rubber|Nitrile]] gloves, which are very commonly used in chemical laboratories, have been found to dissolve rapidly with exposure to DMSO.<ref>{{cite web | publisher = [[Cornell University]] | title = Chemical Hygiene Plan | url = http://www.ehs.cornell.edu/geneva/chp/11.glove.selec.htm | date = September 99}}</ref> 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.<ref>Vignes, Robert (August 2000). [http://www.gaylordchemical.com/bulletins/Vignes-ACS.pdf Dimethyl Sulfoxide (DMSO): A "new" clean, unique, superior solvent], American Chemical Society Annual Meeting</ref> Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides; at a low temperature, this reaction produces the oxidant for [[Swern oxidation]].
Recently, it was found that DMSO waste disposal into [[sewers]] can cause environmental odor problems in cities: Waste water bacteria transform DMSO under [[Hypoxia (environmental)|hypoxic]] (anoxic) conditions into [[dimethyl sulfide]] (DMS) that is slightly toxic and has a strong disagreeable odor, similar to rotten cabbage.<ref>{{cite journal
|author= Glindemann, D., Novak, J., Witherspoon, J.
|title= Dimethyl Sulfoxide (DMSO) Waste Residues and Municipal Waste Water Odor by Dimethyl Sulfide (DMS): the North-East WPCP Plant of Philadelphia
|journal= Environmental Science and Technology
|year= 2006
| volume = 40
| issue = 1
|pages=202–207
|doi=10.1021/es051312a S0013-936X(05)01312-X }}
</ref>
==See also==
{{commonscat|dimethyl sulfoxide}}
* [[Dimethyl sulfide]] (DMS), the corresponding sulfide
* [[Dimethyl sulfate]] (also DMS), the corresponding sulfate: a [[mutagenic]] [[alkylation|alkylating]] compound
* [[Methylsulfonylmethane]] (MSM), a related chemical often used as a dietary supplement
==References==
{{Reflist|2}}
{{Urologicals}}
{{Topical products for joint and muscular pain}}
[[Category:Solvents]]
[[Category:Sulfoxides]]
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[[fr:Diméthylsulfoxyde]]
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