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Dimethyl sulfoxide

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"DMSO" redirects here. For other uses, seeDMSO (disambiguation).
Dimethyl sulfoxide
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions
Spacefill model of dimethyl sulfoxide
Spacefill model of dimethyl sulfoxide

A sample of dimethyl sulfoxide
Names
Preferred IUPAC name
(Methanesulfinyl)methane
Systematic IUPAC name
(Methanesulfinyl)methane(substitutive)
Dimethyl(oxido)sulfur(additive)
Other names
Methylsulfinylmethane
Methyl sulfoxide (2:1), Dermasorb[1]
Identifiers
3D model (JSmol)
Abbreviations DMSO, Me2SO
506008
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.604Edit this at Wikidata
EC Number
  • 200-664-3
1556
KEGG
MeSH Dimethyl+sulfoxide
RTECS number
  • PV6210000
UNII
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3checkY
    Key: IAZDPXIOMUYVGZ-UHFFFAOYSA-NcheckY
  • InChI=1/C2H6OS/c1-4(2)3/h1-2H3
    Key: IAZDPXIOMUYVGZ-UHFFFAOYAR
  • CS(=O)C
  • CS(C)=O
Properties
C2H6OS
Molar mass 78.13g·mol−1
Appearance Colourless liquid
Density 1.1004g⋅cm−3
Melting point 19 °C (66 °F; 292 K)
Boiling point 189 °C (372 °F; 462 K)
Miscible
SolubilityinDiethyl ether Not soluble
Vapor pressure 0.556 millibars or 0.0556 kPa at 20 °C[2]
Acidity(pKa) 35[3]
1.479
εr= 48
Viscosity 1.996cPat 20 °C
Structure
Cs
Trigonal pyramidal
3.96D
Pharmacology
G04BX13(WHO)M02AX03(WHO)
Hazards
Occupational safety and health(OHS/OSH):
Main hazards
 Irritant
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 89 °C (192 °F; 362 K)
Safety data sheet(SDS) Oxford MSDS
Related compounds
Relatedsulfoxides
 Diethyl sulfoxide
Related compounds
Supplementary data page
Dimethyl sulfoxide (data page)
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Dimethyl sulfoxide(DMSO) is anorganosulfur compoundwith theformula(CH3)2SO.This colorless liquid is thesulfoxidemost widely used commercially. It is an importantpolaraprotic solventthat dissolves bothpolar and nonpolarcompounds and ismisciblein a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave agarlic-like taste in the mouth after DMSO is absorbed by skin.[5]

In terms of chemical structure, the molecule has idealizedCssymmetry.It has atrigonal pyramidal molecular geometryconsistent with other three-coordinate S(IV) compounds,[6]with anonbonded electron pairon the approximatelytetrahedralsulfur atom.

Synthesis and production

[edit]

Dimethyl sulfoxide was first synthesized in 1866 by the Russian scientistAlexander Zaytsev,who reported his findings in 1867.[7]Its modern use as an industrial solvent began through popularization by Thor Smedslund at the Stepan Chemical Company.[8]Dimethyl sulfoxide is produced industrially fromdimethyl sulfide,a by-product of theKraft process,by oxidation with oxygen ornitrogen dioxide.[9]

Reactions

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Reactions with electrophiles

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The sulfur center in DMSO isnucleophilictoward softelectrophilesand the oxygen is nucleophilic toward hard electrophiles. Withmethyl iodideit formstrimethylsulfoxonium iodide,[(CH3)3SO]I:

(CH3)2SO + CH3I → [(CH3)3SO]I

This salt can bedeprotonatedwithsodium hydrideto form thesulfurylide:

[(CH3)3SO]I + NaH → (CH3)2S(CH2)O + NaI + H2

Acidity

[edit]

The methyl groups of DMSO are only weakly acidic, with apKa= 35.For this reason, the basicities of many weakly basic organic compounds have been examined in this solvent.

Deprotonation of DMSO requires strong bases likelithium diisopropylamideandsodium hydride.Stabilization of the resultantcarbanionis provided by the S(O)R group. The sodium derivative of DMSO formed in this way is referred to asdimsyl sodium.It is a base, e.g., for the deprotonation ofketonesto form sodiumenolates,phosphonium saltsto formWittig reagents,andformamidiniumsalts to formdiaminocarbenes.It is also a potent nucleophile.

Oxidant

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Inorganic synthesis,DMSO is used as a mild oxidant.[10]It forms the basis of several selectivesulfonium-based oxidation reactionsincluding thePfitzner–Moffatt oxidation,Corey–Kim oxidationand theSwern oxidation.[11]TheKornblum oxidationis conceptually similar. These all involve formation of an intermediatesulfoniumspecies (R2S+X where X is a heteroatom)

Ligand and Lewis base

[edit]

Related to its ability to dissolve many salts, DMSO is a commonligandincoordination chemistry.[12]Illustrative is the complexdichlorotetrakis(dimethyl sulfoxide)ruthenium(II)(RuCl2(dmso)4). In this complex, three DMSO ligands are bonded torutheniumthrough sulfur. The fourth DMSO is bonded through oxygen. In general, the oxygen-bonded mode is more common.

In carbon tetrachloride solutions DMSO functions as a Lewis base with a variety of Lewis acids such asI2,phenols,trimethyltin chloride,metalloporphyrins, and the dimerRh2Cl2(CO)4.The donor properties are discussed in theECW model.The relative donor strength of DMSO toward a series of acids, versus other Lewis bases, can be illustrated byC-B plots.[13][14]

Applications

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Solvent

[edit]
Distillation of DMSO requires a partial vacuum to achieve a lower boiling point.

DMSO is apolar aprotic solventand is less toxic than other members of this class, such asdimethylformamide,dimethylacetamide,N-methyl-2-pyrrolidone,andhexamethylphosphoramide(HMPA). DMSO is frequently used as asolventfor chemical reactions involving salts, most notablyFinkelstein reactionsand othernucleophilic substitutions.It is also extensively used as an extractant in biochemistry and cell biology.[15]Because DMSO is only weakly acidic, it tolerates relatively strong bases and as such has been extensively used in the study ofcarbanions.A set of non-aqueouspKavalues (C-H, O-H, S-H and N-H acidities) for thousands of organic compounds have been determined in DMSO solution.[16][17]

Because of its high boiling point, 189 °C (372 °F), 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 conventionalrotary evaporation.One technique to fully recover samples is removal of the organic solvent by evaporation followed by addition of water (to dissolve DMSO) andcryodesiccationto 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, 18.5 °C (65.3 °F), means that at, or just below, room temperature it is a solid, which can limit its utility in some chemical processes (e.g.crystallizationwith cooling).

In itsdeuteratedform (DMSO-d6), it is a useful solvent forNMRspectroscopy, 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-d6are its high viscosity, which broadens signals, and itshygroscopicity,which leads to an overwhelming H2O resonance in the1H-NMR spectrum. It is often mixed withCDCl3orCD2Cl2for lower viscosity and melting points.

DMSO is used as a solvent inin vitroandin vivodrug testing.

DMSO is used to dissolve test compounds inin vitrodrug discovery[18][19]anddrug design[20]screeningprograms, includinghigh-throughput screeningprograms.[19][20]This is because it is able to dissolve bothpolarandnonpolarcompounds,[18][20]can be used to maintainstock solutionsof test compounds (important when working with a largechemical library),[19]is readilymisciblewith water andcell culture media,and has a high boiling point (this improves the accuracy of test compound concentrations by reducing room temperature evaporation).[18]One limitation with DMSO is that it can affectcell linegrowth and viability, with low DMSO concentrations sometimes stimulating cell growth, and high DMSO concentrations sometimes inhibiting or killing cells.[18]

DMSO is used as a vehicle inin vivostudies of test compounds. It has, for example, been employed as a co-solvent to assist absorption of theflavonol glycosideIcariinin thenematodewormCaenorhabditis elegans.[21]As with its use inin vitrostudies, DMSO has some limitations inanimal models.[22][23]Pleiotropiceffects can occur and, if DMSO control groups are not carefully planned, then solvent effects can falsely be attributed to the prospective drug.[22]For example, even a very low dose of DMSO has a powerful protective effect againstparacetamol(acetaminophen)-induced liver injury in mice.[23]

DMSO is finding increased use in manufacturing processes to produce microelectronic devices.[24]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 an effectivepaint stripper,being safer than many of the others such asnitromethaneanddichloromethane.

Biology

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DMSO is used inpolymerase chain reaction(PCR) to inhibitsecondary structuresin theDNA templateor theDNA primers.It is added to the PCR mix before reacting, where it interferes with the self-complementarity of the DNA, minimizing interfering reactions.[25]

DMSO in a PCR is applicable for supercoiled plasmids (to relax before amplification) or DNA templates with highGC-content(to decreasethermostability). For example, 10% final concentration of DMSO in the PCR mixture with Phusion decreases primer annealing temperature (i.e. primer melting temperature) by 5.5–6.0 °C (9.9–10.8 °F).[26]

It is well known as a reversible cell cycle arrester at phase G1 of human lymphoid cells.[27]

DMSO may also be used as acryoprotectant,added to cell media to reduce ice formation and thereby prevent cell death during the freezing process.[28]Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at −80 °C (−112 °F) or stored inliquid nitrogensafely.

In cell culture, DMSO is used to inducedifferentiationofP19 embryonic carcinoma cellsintocardiomyocytesandskeletal muscle cells.

Medicine

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Use of DMSO in medicine dates from around 1963, when anOregon Health & Science UniversityMedical School team, headed byStanley Jacob,discovered it could penetrate the skin and other membranes without damaging them and could carry other compounds into a biological system. In medicine, DMSO is predominantly used as a topicalanalgesic,a vehicle for topical application of pharmaceuticals, as ananti-inflammatory,and anantioxidant.[29]Because DMSO increases the rate of absorption of some compounds throughbiological tissues,includingskin,it is used in sometransdermaldrug deliverysystems. Its effect may be enhanced with the addition ofEDTA.It is frequently compounded with antifungal medications, enabling them to penetrate not just skin but also toenails and fingernails.[30]

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 withinterstitial cystitis.[31]A 1978 study concluded that DMSO broughtsignificantrelief to the majority of the 213 patients with inflammatorygenitourinarydisorders that were studied.[32]The authors recommended DMSO for genitourinary inflammatory conditions not caused by infection or tumor in which symptoms were severe or patients failed to respond to conventional therapy.

Ininterventional radiology,DMSO is used as a solvent forethylene vinyl alcoholin theOnyxliquid embolic agent, which is used inembolization,the therapeutic occlusion of blood vessels.

IncryobiologyDMSO has been used as acryoprotectantand is still an important constituent of cryoprotectantvitrificationmixtures 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 ofembryonic stem cellsandhematopoietic 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,etc.) a mixture of 10% DMSO with 90%EMEM(70% EMEM + 30% fetal bovine serum + antibiotic mixture) is used. As part of anautologousbone marrow transplantthe DMSO is re-infused along with the patient's ownhematopoietic stem cells.

DMSO is metabolized bydisproportionationtodimethyl sulfideanddimethyl 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 bornehalitosissymptom.

Alternative medicine

[edit]

DMSO is marketed as analternative medicine.Its popularity as an alternative cure is stated to stem from a60 Minutesdocumentary in 1980 featuring an early proponent.[33]However, DMSO is an ingredient in some products listed by the U.S. FDA as fake cancer cures[34]and the FDA has had a running battle with distributors.[33]One such distributor is Mildred Miller, who promoted DMSO for a variety of disorders and was consequently convicted ofMedicare fraud.[33]

The use of DMSO as an alternative treatment for cancer is of particular concern, as it has been shown to interfere with a variety ofchemotherapydrugs, includingcisplatin,carboplatin,andoxaliplatin.[35]There is insufficient evidence to support the hypothesis that DMSO has any effect,[36]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 theusual disclaimer.

Veterinary medicine

[edit]

DMSO is commonly used in veterinary medicine as alinimentforhorses,alone or in combination with other ingredients. In the latter case, often, the intended function of the DMSO is as a solvent, to carry the other ingredients across the skin. Also in horses, DMSO is used intravenously, again alone or in combination with other drugs. It is used alone for the treatment of increased intracranial pressure and/or cerebral edema in horses.[citation needed]

Taste

[edit]

The perceived garlic taste upon skin contact with DMSO may be due tononolfactoryactivation ofTRPA1receptors intrigeminal ganglia.[37]Unlikedimethylanddiallyldisulfides (which have odors resembling garlic),mono-andtri-sulfides (which typically have foul odors), and similar odiferous sulfur compounds, the pure chemical DMSO is odorless.

Safety

[edit]

Toxicity

[edit]

DMSO is a non-toxic solvent with amedian lethal dosehigher than ethanol (DMSO: LD50,oral, rat, 14,500 mg/kg;[38][39]ethanol: LD50,oral, rat, 7,060 mg/kg[40]).

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.[41]

Because DMSO easily penetrates theskin,substances dissolved in DMSO may quickly be absorbed.Gloveselection is important when working with DMSO.Butyl rubber,fluoroelastomer,neoprene,or thick (15mil/ 0.4mm)latexgloves are recommended.[42]Nitrilegloves, which are very commonly used in chemical laboratories, may protect from brief contact but have been found to degrade rapidly with exposure to DMSO.[43]

Regulation

[edit]

In Australia, it is listed as aSchedule 4 (S4)Drug, and a company has been prosecuted for adding it to products as a preservative.[44]

Clinical safety

[edit]

Early clinical trials with DMSO were stopped because of questions about its safety, especially its ability to harm the eye. The most commonly reported side effects include headaches and burning and itching on contact with the skin. Strong allergic reactions have been reported.[full citation needed]

On September 9, 1965,The Wall Street Journalreported 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.[45]Clinical researchusing DMSO was halted and did not begin again until theNational Academy of Sciences(NAS) published findings in favor of DMSO in 1972.[46]In 1978, the US FDA approved DMSO for treatinginterstitial 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 followingtraumatic brain injury.[46]

DMSO exposure to developing mouse brains can produce brain degeneration. Thisneurotoxicitycould be detected atdosesas low as 0.3mL/kg, a level exceeded in children exposed to DMSO duringbone marrow transplant.[47]

Odor problem

[edit]

DMSO disposed intosewerscan cause odor problems in municipal effluents: waste waterbacteriatransform DMSO underhypoxic(anoxic) conditions intodimethyl sulfide(DMS) that has a strong disagreeable odor, similar to rotten cabbage.[48]However, chemically pure DMSO is odorless because of the lack of C-S-C (sulfide) and C-S-H (mercaptan) linkages. Deodorization of DMSO is achieved by removing the odorous impurities it contains.[49]

Explosion hazard

[edit]

Dimethyl sulfoxide can produce an explosive reaction when exposed toacyl chlorides;at a low temperature, this reaction produces theoxidantforSwern oxidation.

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.[50]

See also

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References

[edit]
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  2. ^"Dimethyl Sulfoxide (DMSO) -- Technical".Atofina Chemicals, inc.Retrieved26 May2007.
  3. ^Matthews WS, Bares JE, Bartmess JE, Bordwell FG, Cornforth FJ, Drucker GE, Margolin Z, McCallum RJ, McCollum GJ, Vanier NR (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution".J. Am. Chem. Soc.97(24): 7006–7014.doi:10.1021/ja00857a010.
  4. ^"Dimethyl sulfoxide".pubchem.ncbi.nlm.nih.gov.
  5. ^Novak KM, ed. (2002).Drug Facts and Comparisons(56th ed.). St. Louis, Missouri: Wolters Kluwer Health. p.2345.ISBN978-1-57439-110-7.
  6. ^Thomas R, Shoemaker CB, Eriks K (1966). "The Molecular and Crystal Structure of Dimethyl Sulfoxide, (H3C)2SO ".Acta Crystallogr.21(1): 12–20.Bibcode:1966AcCry..21...12T.doi:10.1107/S0365110X66002263.
  7. ^von Demselben (1867). "Ueber die Einwirkung von Saltpetersäure auf Schwefelmethyl und Schwefeläthyl" [On the effect of nitric acid on methyl sulfide and ethyl sulfide]. In Erlenmeyer, E.; Rieckher, T.; Volhard, J.; Liebig, J.; Wöhler, F. (eds.).Annalen der Pharmacie(in German). Meyer; Winter. p. 148.
  8. ^Gergel, Max G.(March 1977).Excuse me sir, would you like to buy a kilo of isopropyl bromide?.Pierce Chemical. p. 145.
  9. ^Roy, Kathrin-Maria (15 June 2000), "Sulfones and Sulfoxides",Ullmann's Encyclopedia of Industrial Chemistry,Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA,doi:10.1002/14356007.a25_487,ISBN3527306730
  10. ^Epstein WW, Sweat FW (March 1967). "Dimethyl Sulfoxide Oxidations".Chemical Reviews.67(3): 247–260.doi:10.1021/cr60247a001.PMID6042131.
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  28. ^ Pegg, DE (2007). "Principles of Cryopreservation". In Day JG, Stacey GN (eds.).Cryopreservation and Freeze-Drying Protocols.Methods in Molecular Biology. Vol. 368. Humana Press. pp. 39–57.doi:10.1007/978-1-59745-362-2_3.ISBN978-1-58829-377-0.ISSN1064-3745.PMID18080461.{{cite book}}:|journal=ignored (help)
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  46. ^abhttps:// fda.gov/ForIndustry/ImportProgram/ImportAlerts/ucm162294.htm[dead link]
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  48. ^Glindemann D, Novak J, Witherspoon J (January 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.Bibcode:2006EnST...40..202G.doi:10.1021/es051312a.PMID16433352.
  49. ^US application 2009005601A1,George Kvakovszky; David Villarrubia II & Scott Stevenson et al., "Process for preparing low malodorous dimethyl sulfoxide", published 2009, assigned to Gaylord Chemical Company LLC
  50. ^Roth, Lutz; Weller, Ursula (August 2000).Gefährliche Chemische Reaktionen[Dangerous Chemical Reactions]. Ecomed Sicherheit (in German). Landsberg/Lech: Verlagsgruppe Hüthig Jehle Rehm.ISBN3-609-73090-0.CD-ROM:ISBN3-609-48040-8
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