Dimethyl sulfoxide
Overview
 
Dimethyl sulfoxide is an organosulfur compound with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 (CH3)2SO. This colorless liquid is an important 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 penetrates the skin very readily, giving it the unusual property for many individuals of being secreted onto the surface of the tongue after contact with the skin and causing a garlic
Garlic
Allium sativum, commonly known as garlic, is a species in the onion genus, Allium. Its close relatives include the onion, shallot, leek, chive, and rakkyo. Dating back over 6,000 years, garlic is native to central Asia, and has long been a staple in the Mediterranean region, as well as a frequent...

-like taste in the mouth.
It was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867.
Encyclopedia
Dimethyl sulfoxide is an organosulfur compound with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 (CH3)2SO. This colorless liquid is an important 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 penetrates the skin very readily, giving it the unusual property for many individuals of being secreted onto the surface of the tongue after contact with the skin and causing a garlic
Garlic
Allium sativum, commonly known as garlic, is a species in the onion genus, Allium. Its close relatives include the onion, shallot, leek, chive, and rakkyo. Dating back over 6,000 years, garlic is native to central Asia, and has long been a staple in the Mediterranean region, as well as a frequent...

-like taste in the mouth.

Synthesis and production

It was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867. Dimethyl sulfoxide is a by-product of kraft pulping. Oxidation of dimethyl sulfide
Dimethyl sulfide
Dimethyl sulfide or methylthiomethane is an organosulfur compound with the formula 2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize,...

 with oxygen or nitrogen dioxide
Nitrogen dioxide
Nitrogen dioxide is the chemical compound with the formula it is one of several nitrogen oxides. is an intermediate in the industrial synthesis of nitric acid, millions of tons of which are produced each year. This reddish-brown toxic gas has a characteristic sharp, biting odor and is a prominent...

 gives DMSO.

Solvent

DMSO is a polar aprotic solvent and is less toxic than other members of this class, such as dimethylformamide
Dimethylformamide
Dimethylformamide is an organic compound with the formula 2NCH. Commonly abbreviated as DMF , this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions...

, dimethylacetamide
Dimethylacetamide
Dimethylacetamide is the organic compound with the formula CH3CN2. This colorless, water miscible, high boiling liquid is commonly used as a polar solvent in organic chemistry. DMAc is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.The chemical reactions...

, N-methyl-2-pyrrolidone
Methylpyrrolidone
N-Methyl-2-pyrrolidone is a chemical compound with 5-membered lactam structure. It is a clear to slightly yellow liquid miscible with water and solvents like ethyl acetate, chloroform, benzene and lower alcohols or ketones. It also belongs to the class of dipolar aprotic solvents which includes...

, and HMPA
Hexamethylphosphoramide
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide having the formula [2N]3PO. This colorless liquid is a useful polar aprotic solvent and additive in organic synthesis.-Structure and reactivity:...

. DMSO is frequently used as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

 for chemical reactions involving salts, most notably Finkelstein reaction
Finkelstein reaction
The Finkelstein reaction, named for the German chemist Hans Finkelstein , is an SN2 reaction that involves the exchange of one halogen atom for another...

s and other nucleophilic substitution
Nucleophilic substitution
In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms called the leaving group; the positive or partially positive...

s. It is also extensively used as an extractant in biochemistry and cell biology. Because DMSO is only weakly acidic, it tolerates relatively strong bases and as such has been extensively used in the study of carbanion
Carbanion
A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. The carbanion exists in a trigonal pyramidal geometry. Formally a carbanion is the conjugate base of a carbon acid.where B...

s. A set of non-aqueous pKa
PKA
PKA, pKa, or other similar variations may stand for:* pKa, the symbol for the acid dissociation constant at logarithmic scale* Protein kinase A, a class of cAMP-dependent enzymes* Pi Kappa Alpha, the North-American social fraternity...

 values (C-H, O-H, S-H and N-H acidities) for thousands of organic compounds have been determined in DMSO solution.

Because of its high boiling point (189 °C; 372.2 °F 462 K), DMSO evaporates slowly at normal atmospheric pressure. Samples dissolved in DMSO cannot be as easily recovered compared to other solvents, as it is very difficult to remove all traces of DMSO by conventional rotary evaporation. Reactions conducted in DMSO are often diluted with water to precipitate or phase-separate products. The relatively high freezing point (18.5 °C; 65.3 °F; 292 K) 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. crystallization
Crystallization
Crystallization is the process of formation of solid crystals precipitating from a solution, melt or more rarely deposited directly from a gas. Crystallization is also a chemical solid–liquid separation technique, in which mass transfer of a solute from the liquid solution to a pure solid...

 with cooling).

In its deuterated
Deuterium
Deuterium, also called heavy hydrogen, is one of two stable isotopes of hydrogen. It has a natural abundance in Earth's oceans of about one atom in of hydrogen . Deuterium accounts for approximately 0.0156% of all naturally occurring hydrogen in Earth's oceans, while the most common isotope ...

 form (DMSO-d6
Deuterated DMSO
Deuterated DMSO, also known as dimethyl sulfoxide-d6, is an isotopologue of dimethyl sulfoxide ) with chemical formula in which the hydrogen atoms are replaced with their isotope deuterium...

), it is a useful but expensive solvent for NMR
Nuclear magnetic resonance
Nuclear magnetic resonance is a physical phenomenon in which magnetic nuclei in a magnetic field absorb and re-emit electromagnetic radiation...

 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-d6
Deuterated DMSO
Deuterated DMSO, also known as dimethyl sulfoxide-d6, is an isotopologue of dimethyl sulfoxide ) with chemical formula in which the hydrogen atoms are replaced with their isotope deuterium...

 are its high viscosity, which broadens signals, and its hygroscopicity, which leads to an overwhelming H2O resonance in the 1H NMR spectrum. It is often mixed with CDCl3
Deuterated chloroform
Deuterated chloroform , is an isotopologue of chloroform in which the hydrogen atom is replaced with a deuterium isotope . Deuterated chloroform is a common solvent used in NMR spectroscopy of organic molecules....

 or CD2Cl2
Deuterated dichloromethane
Deuterated dichloromethane is a form of dichloromethane in which the hydrogen atoms are replaced with deuterium isotope . Deuterated DCM is not a common solvent used in NMR spectroscopy as it is reasonably expensive....

 for lower viscosity and melting points.

DMSO is finding increased 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). It also used in biopreservation
Biopreservation
Biopreservation is the use of natural or controlled microbiota or antimicrobials as a way of preserving food and extending its shelf life. Beneficial bacteria or the fermentation products produced by these bacteria are used in biopreservation to control spoilage and render pathogens inactive in food...

 especially stem cell banking. DMSO is an effective paint stripper
Paint stripper
Paint stripper, or paint remover, is the generic name given to solvent mixtures designed to remove paint and other finishes and also to clean the underlying surface. The principal active ingredient is usually dichloromethane...

, being safer than many of the others such as nitromethane
Nitromethane
Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...

 and dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

.

Because of its ability to dissolve many kinds of compounds, DMSO plays a role in sample management and high-throughput screening
High-throughput screening
High-throughput screening is a method for scientific experimentation especially used in drug discovery and relevant to the fields of biology and chemistry. Using robotics, data processing and control software, liquid handling devices, and sensitive detectors, High-Throughput Screening allows a...

 operations in drug design.

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 (pKa=35) due to the stabilization of the resultant carbanion
Carbanion
A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. The carbanion exists in a trigonal pyramidal geometry. Formally a carbanion is the conjugate base of a carbon acid.where B...

 by the S(O)R group, and so are deprotonated with strong bases like lithium diisopropylamide
Lithium diisopropylamide
Lithium diisopropylamide is the chemical compound with the formula [2CH]2NLi. Generally abbreviated LDA, it is a strong base used in organic chemistry for the deprotonation of weakly acidic compounds. The reagent has been widely accepted because it is soluble in non-polar organic solvents and it...

 and sodium hydride
Sodium hydride
Sodium hydride is the chemical compound with the empirical formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H− ions, in contrast to the more molecular hydrides such as...

. 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
Deprotonation
Deprotonation is the removal of a proton from a molecule, forming the conjugate base.The relative ability of a molecule to give up a proton is measured by its pKa value. A low pKa value indicates that the compound is acidic and will easily give up its proton to a base...

 of ketones to form sodium enolates, phosphonium salt
Phosphonium salt
A phosphonium salt is a salt containing the phosphonium ion such as phosphonium iodide . More commonly, phosphonium refers to a quaternary organic derivative such as tetraphenylphosphonium chloride, 4P+ Cl- and tetramethylphosphonium iodide, [P4]+I−.Alkyltriphenylphosphonium salts are widely...

s to form Wittig reagents, and formamidinium
Formamidinium
Formamidinium cations are positively charged organic chemical compounds which can be represented by the chemical formula [R2N-CH=NR2]+.-Chemical applications:...

 salts to form diaminocarbenes.

DMSO reacts with methyl iodide to form trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides....

, [(CH3)3SO]I, which can be deprotonated with sodium hydride
Sodium hydride
Sodium hydride is the chemical compound with the empirical formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H− ions, in contrast to the more molecular hydrides such as...

 to form the sulfur
Sulfur
Sulfur or sulphur is the chemical element with atomic number 16. In the periodic table it is represented by the symbol S. It is an abundant, multivalent non-metal. Under normal conditions, sulfur atoms form cyclic octatomic molecules with chemical formula S8. Elemental sulfur is a bright yellow...

 ylide
Ylide
An ylide or ylid is a neutral dipolar molecule containing a formally negatively charged atom directly attached to a hetero atom with a formal positive charge , and in which both atoms have full octets of electrons. Ylides are thus 1,2-dipolar compounds...

:2SO + CH3I → [(CH3)3SO]I
[(CH3)3SO]I + NaH → [(CH3)2CH2SO + NaI + H2


In organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

, DMSO is used as a mild oxidant, as illustrated by the Pfitzner-Moffatt oxidation
Pfitzner-Moffatt oxidation
The Pfitzner–Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a chemical reaction which describes the oxidation of primary and secondary alcohols by dimethyl sulfoxide activated with a carbodiimide, such as dicyclohexylcarbodiimide...

 and the Swern oxidation
Swern oxidation
The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine...

.

DMSO is a common ligand
Ligand
In coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...

 in coordination chemistry. The complex dichlorotetrakis(dimethyl sulfoxide)ruthenium(II), RuCl2(dmso)4, features DMSO bonded to ruthenium
Ruthenium
Ruthenium is a chemical element with symbol Ru and atomic number 44. It is a rare transition metal belonging to the platinum group of the periodic table. Like the other metals of the platinum group, ruthenium is inert to most chemicals. The Russian scientist Karl Ernst Claus discovered the element...

 through sulfur and through oxygen.

Biology

DMSO is used in PCR to inhibit secondary structures
Stem-loop
Stem-loop intramolecular base pairing is a pattern that can occur in single-stranded DNA or, more commonly, in RNA. The structure is also known as a hairpin or hairpin loop. It occurs when two regions of the same strand, usually complementary in nucleotide sequence when read in opposite directions,...

 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, minimizing interfering reactions.

DMSO may also be used as a cryoprotectant
Cryoprotectant
A cryoprotectant is a substance that is used to protect biological tissue from freezing damage . Arctic and Antarctic insects, fish, amphibians and reptiles create cryoprotectants in their bodies to minimize freezing damage during cold winter periods. Insects most often use sugars or polyols as...

, added to cell media to prevent cell death during the freezing process. Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at -80°C or stored in liquid nitrogen
Liquid nitrogen
Liquid nitrogen is nitrogen in a liquid state at a very low temperature. It is produced industrially by fractional distillation of liquid air. Liquid nitrogen is a colourless clear liquid with density of 0.807 g/mL at its boiling point and a dielectric constant of 1.4...

 safely.

Medicine

Use of DMSO in medicine dates from around 1963, when an Oregon Health & Science University
Oregon Health & Science University
Oregon Health & Science University is a public university in Oregon with a main campus, including two hospitals, in Portland and a smaller campus in Hillsboro...

 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 medicine, DMSO is predominantly used as a topical analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....

, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory
Anti-inflammatory
Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. Anti-inflammatory drugs make up about half of analgesics, remedying pain by reducing inflammation as opposed to opioids, which affect the central nervous system....

, and an antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

. Because DMSO increases the rate of absorption of some compounds through organic tissues
Biological tissue
Tissue is a cellular organizational level intermediate between cells and a complete organism. A tissue is an ensemble of cells, not necessarily identical, but from the same origin, that together carry out a specific function. These are called tissues because of their identical functioning...

, including skin
Skin
-Dermis:The dermis is the layer of skin beneath the epidermis that consists of connective tissue and cushions the body from stress and strain. The dermis is tightly connected to the epidermis by a basement membrane. It also harbors many Mechanoreceptors that provide the sense of touch and heat...

, it can be used as a drug delivery system. It is frequently compounded with antifungal medications, enabling them to penetrate not just skin but also toe and fingernails.

In cryobiology
Cryobiology
Cryobiology is the branch of biology that studies the effects of low temperatures on living things. The word cryobiology is derived from the Greek words "cryo" = cold, "bios" = life, and "logos" = science. In practice, cryobiology is the study of biological material or systems at temperatures below...

 DMSO has been used as a cryoprotectant
Cryoprotectant
A cryoprotectant is a substance that is used to protect biological tissue from freezing damage . Arctic and Antarctic insects, fish, amphibians and reptiles create cryoprotectants in their bodies to minimize freezing damage during cold winter periods. Insects most often use sugars or polyols as...

 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, Media and 30% fetal bovine serum
Fetal bovine serum
Fetal bovine serum or FBS is the portion of plasma remaining after coagulation of blood, during which process the plasma protein fibrinogen is converted to fibrin and remains behind in the clot. Fetal bovine serum comes from the blood drawn from a bovine fetus via a closed system of collection at...

. 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 an autologous bone marrow transplant
Bone marrow transplant
Hematopoietic stem cell transplantation is the transplantation of multipotent hematopoietic stem cell or blood, usually derived from bone marrow, peripheral blood stem cells, or umbilical cord blood...

 the DMSO is re-infused along with the patient's own hematopoietic stem cells.

In a 1978 study at the Cleveland Clinic
Cleveland Clinic
The Cleveland Clinic is a multispecialty academic medical center located in Cleveland, Ohio, United States. The Cleveland Clinic is currently regarded as one of the top 4 hospitals in the United States as rated by U.S. News & World Report...

 Foundation in Cleveland, Ohio
Cleveland, Ohio
Cleveland is a city in the U.S. state of Ohio and is the county seat of Cuyahoga County, the most populous county in the state. The city is located in northeastern Ohio on the southern shore of Lake Erie, approximately west of the Pennsylvania border...

, researchers concluded that DMSO brought significant relief to the majority of the 213 patients with inflammatory genitourinary disorders that were studied. 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.

DMSO has been examined for the treatment of numerous conditions and ailments, but the U.S. Food and Drug Administration
Food and Drug Administration
The Food and Drug Administration is an agency of the United States Department of Health and Human Services, one of the United States federal executive departments...

 (FDA) has approved its use only for the symptomatic relief of patients with interstitial cystitis
Interstitial cystitis
Interstitial cystitis or bladder pain syndrome is a chronic, oftentimes severely debilitating disease of the urinary bladder...

.

In interventional radiology
Interventional radiology
Interventional radiology is a specialty of radiology, in which image-guided procedures are used to diagnose and treat a multitude of diseases across all body systems...

, DMSO is used as a solvent for Ethylene Vinyl Alcohol
EVOH
Ethylene Vinyl Alcohol, commonly abbreviated EVOH, is a formal copolymer of ethylene and vinyl alcohol. Because the latter monomer mainly exists as its tautomer acetaldehyde, the copolymer is prepared by polymerization of ethylene and vinyl acetate to give the ethylene vinyl acetate copolymer...

 in the Onyx
Onyx (Interventional radiology)
In interventional radiology Onyx is a trade name for a copolymer uesd for embolisation therapy, which involves the occlusion of blood vessels. It is a liquid embolic agent. Onyx is produced and sold by ev3 Inc. - Components :...

 liquid embolic agent, which is used in embolisation, the therapeutic occlusion of blood vessels.

Veterinary medicine

DMSO is commonly used in veterinary medicine as a liniment
Liniment
Liniment , from the Latin linere, to anoint, is a medicated topical preparation for application to the skin. Preparations of this type are also called balm...

 for horse
Horse
The horse is one of two extant subspecies of Equus ferus, or the wild horse. It is a single-hooved mammal belonging to the taxonomic family Equidae. The horse has evolved over the past 45 to 55 million years from a small multi-toed creature into the large, single-toed animal of today...

s, 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.

Safety

DMSO by itself has low toxicity.

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 halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972. In 1978, the U.S. FDA approved DMSO for treating interstitial cystitis
Interstitial cystitis
Interstitial cystitis or bladder pain syndrome is a chronic, oftentimes severely debilitating disease of the urinary bladder...

. In 1980, the U.S. Congress held hearings on claims that the FDA was slow in approving DMSO for other medical uses. In 2007, the U.S. 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 0.3 mL/kg, a level exceeded in children exposed to DMSO during certain medical treatments.

Glove selection is important when working with DMSO. Thick rubber gloves are recommended. Nitrile
Nitrile rubber
Nitrile rubber, also known as Buna-N, Perbunan, or NBR, is a synthetic rubber copolymer of acrylonitrile and butadiene. Trade names include Nipol, Krynac and Europrene....

 gloves, which are very commonly used in chemical laboratories, have been found to dissolve rapidly with exposure to DMSO. Because DMSO easily penetrates the skin, substances dissolved in DMSO may be quickly absorbed. For instance, a solution of sodium cyanide
Sodium cyanide
Sodium cyanide is an inorganic compound with the formula NaCN. This highly toxic colorless salt is used mainly in gold mining but has other niche applications...

 in DMSO can cause cyanide
Cyanide
A cyanide is a chemical compound that contains the cyano group, -C≡N, which consists of a carbon atom triple-bonded to a nitrogen atom. Cyanides most commonly refer to salts of the anion CN−. Most cyanides are highly toxic....

 poisoning through skin contact. Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides; at a low temperature, this reaction produces the oxidant for Swern oxidation
Swern oxidation
The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine...

.

Recently, DMSO disposed into sewers
Sanitary sewer
A sanitary sewer is a separate underground carriage system specifically for transporting sewage from houses and commercial buildings to treatment or disposal. Sanitary sewers serving industrial areas also carry industrial wastewater...

 caused odor problems in cities: waste water bacteria transform DMSO under hypoxic
Hypoxia (environmental)
Hypoxia, or oxygen depletion, is a phenomenon that occurs in aquatic environments as dissolved oxygen becomes reduced in concentration to a point where it becomes detrimental to aquatic organisms living in the system...

 (anoxic) conditions into dimethyl sulfide
Dimethyl sulfide
Dimethyl sulfide or methylthiomethane is an organosulfur compound with the formula 2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize,...

 (DMS) that has a strong disagreeable odor, similar to rotten cabbage.

See also

  • Varying oxidation of sulfur
    • Dimethyl sulfide
      Dimethyl sulfide
      Dimethyl sulfide or methylthiomethane is an organosulfur compound with the formula 2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize,...

       (DMS), the corresponding sulfide, also produced by marine phytoplankton and emitted to the oceanic atmosphere where it is oxidized to DMSO, SO2 and sulfate
    • Methylsulfonylmethane
      Methylsulfonylmethane
      Methylsulfonylmethane is an organosulfur compound with the formula 2SO2. It is also known by several other names including DMSO2, methyl sulfone, and dimethyl sulfone. This colorless solid features the sulfonyl functional group and is considered relatively inert chemically...

       (MSM), a related chemical often marketed as a dietary supplement
  • Related compounds with methyl on oxygen
    • Dimethyl sulfite
      Dimethyl sulfite
      Dimethyl sulfite is a sulfite ester with the chemical formula 2SO.Dimethyl sulfite is used as an additive in some polymers to prevent oxidation. It is also a potentially useful high energy battery electrolyte solvent.-Structure and conformation:...

      , the corresponding sulfite
    • Dimethyl sulfate
      Dimethyl sulfate
      Dimethyl sulfate is a chemical compound with formula 2SO2. As the diester of methanol and sulfuric acid, its formula is often written as 2SO4 or even Me2SO4, where CH3 or Me is methyl...

       (also DMS), the corresponding sulfate: a mutagenic alkylating
      Alkylation
      Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...

       compound
    • Methyl methanesulfonate
      Methyl methanesulfonate
      Methyl methanesulfonate is an alkylating agent and a carcinogen. It is also a suspected reproductive toxicant, and may also be a skin/sense organ toxicant. It is used in cancer treatment.-Chemical reactions with DNA:...

      , another methylating agent

External links

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