Dimethyl sulfoxide (DMSO) is an
organosulfur compound with the
formula (
CH3)
2. This colorless liquid is the
sulfoxide most widely used commercially. It is an important
polar
Polar may refer to:
Geography
Polar may refer to:
* Geographical pole, either of two fixed points on the surface of a rotating body or planet, at 90 degrees from the equator, based on the axis around which a body rotates
*Polar climate, the cli ...
aprotic solvent A polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Am ...
that dissolves both
polar and nonpolar compounds and is
miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a
garlic
Garlic (''Allium sativum'') is a species of bulbous flowering plant in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chive, Welsh onion and Chinese onion. It is native to South Asia, Central Asia and northeas ...
-like taste in the mouth after DMSO makes contact with their skin.
In terms of chemical structure, the molecule has idealized
Cs symmetry
Symmetry (from grc, συμμετρία "agreement in dimensions, due proportion, arrangement") in everyday language refers to a sense of harmonious and beautiful proportion and balance. In mathematics, "symmetry" has a more precise definiti ...
. It has a
trigonal pyramidal molecular geometry
In chemistry, a trigonal pyramid is a molecular geometry with one atom at the apex and three atoms at the corners of a trigonal base, resembling a tetrahedron (not to be confused with the tetrahedral geometry). When all three atoms at the corner ...
consistent with other three-coordinate S(IV) compounds, with a
nonbonded electron pair on the approximately
tetrahedral sulfur atom.
Synthesis and production
Dimethyl sulfoxide was first synthesized in 1866 by the Russian scientist
Alexander Zaytsev, who reported his findings in 1867.
Dimethyl sulfoxide is produced industrially from
dimethyl sulfide, a by-product of the
Kraft process, by oxidation with oxygen or
nitrogen dioxide.
Reactions
Reactions with electrophiles
The sulfur center in DMSO is
nucleophilic toward soft
electrophiles and the oxygen is nucleophilic toward hard electrophiles. With
methyl iodide it forms
trimethylsulfoxonium iodide,
3)3SO">CH3)3SO:
:(CH
3)
2SO + CH
3I →
3)3SO">CH3)3SO
This salt can be
deprotonated with
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in ...
to form the
sulfur
Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formul ...
ylide An ylide or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms ...
:
:
3)3SO">CH3)3SO + NaH → (CH
3)
2S(CH
2)O + NaI + H
2
Acidity
The methyl groups of DMSO are only weakly acidic, with a . For this reason, the basicities of many weakly basic organic compounds have been examined in this solvent.
Deprotonation of DMSO requires strong bases like
lithium diisopropylamide and
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in ...
. Stabilization of the resultant
carbanion is provided by the S(O)R group. The sodium derivative of DMSO formed in this way is referred to as ''
dimsyl sodium''. It is a base, e.g., for the deprotonation of
ketones to form sodium
enolates,
phosphonium salts to form
Wittig reagents, and
formamidinium salts to form
diaminocarbenes. It is also a potent nucleophile.
Oxidant
In
organic synthesis, DMSO is used as a mild oxidant. It forms the basis of several selective
sulfonium-based oxidation reactions, including the
Pfitzner–Moffatt oxidation
The Pfitzner–Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a chemical reaction for the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively. The oxidant is a combination of dimethyl ...
,
Corey–Kim oxidation, and
Swern oxidation.
The
Kornblum oxidation
The Kornblum oxidation, named after Nathan Kornblum, is an organic oxidation reaction that converts alkyl halides and tosylates into carbonyl compounds.
Mechanism
Similar to sulfonium-based oxidation of alcohols to aldehydes reactions, the ...
is conceptually similar. These all involve formation of an intermediate
sulfonium
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a "cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula . Together wi ...
species (R
2S
+X where X is a heteroatom).
Ligand and Lewis base
Related to its ability to dissolve many salts, DMSO is a common
ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elect ...
in
coordination chemistry. Illustrative is the complex
dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) (RuCl
2(dmso)
4). In this complex, three DMSO ligands are bonded to
ruthenium through 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 as
I2,
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it r ...
s,
trimethyltin chloride
Trimethyltin chloride is an organotin compound with the formula . It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.
Synthesis
Trimethyltin chloride can be prepared by the redistribution reaction of tetramet ...
, metalloporphyrins, and the dimer
Rh2Cl2(CO)4. The donor properties are discussed in the
ECW model. The relative donor strength of DMSO toward a series of acids, versus other Lewis bases, can be illustrated by
C-B plots.
Applications
Solvent
DMSO is a
polar aprotic solvent and is less toxic than other members of this class, such as
dimethylformamide
Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...
,
dimethylacetamide,
''N''-methyl-2-pyrrolidone, and
hexamethylphosphoramide (HMPA). DMSO is frequently used as a
solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
for chemical reactions involving salts, most notably
Finkelstein reactions and other
nucleophilic substitutions. 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
carbanions. A set of non-aqueous
pKa
PKA may refer to:
* Professionally known as:
** Pen name
** Stage persona
* p''K''a, 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 so ...
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, , 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. One technique to fully recover samples is removal of the organic solvent by evaporation followed by addition of water (to dissolve DMSO) and
cryodesiccation to 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, , means that at, or just below, room temperature it is a solid, which can limit its utility in some chemical processes (e.g.
crystallization with cooling).
In its
deuterated
Isotopic labeling (or isotopic labelling) is a technique used to track the passage of an isotope (an atom with a detectable variation in neutron count) through a reaction, metabolic pathway, or cell. The reactant is 'labeled' by replacing specific ...
form (
DMSO-''d''6), it is a useful solvent for
NMR spectroscopy, 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-''d''
6 are its high viscosity, which broadens signals, and its
hygroscopicity, which leads to an overwhelming H
2O resonance in the
1H-NMR spectrum. It is often mixed with
CDCl3 or
CD2Cl2 for lower viscosity and melting points.
DMSO is also used to dissolve test compounds in ''
in vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology a ...
''
drug discovery and
drug design screening
Screening may refer to:
* Screening cultures, a type a medical test that is done to find an infection
* Screening (economics), a strategy of combating adverse selection (includes sorting resumes to select employees)
* Screening (environmental), ...
programs, including
high-throughput screening programs.
This is because it is able to dissolve both
polar
Polar may refer to:
Geography
Polar may refer to:
* Geographical pole, either of two fixed points on the surface of a rotating body or planet, at 90 degrees from the equator, based on the axis around which a body rotates
*Polar climate, the cli ...
and
nonpolar compounds,
can be used to maintain
stock solutions of test compounds (important when working with a large
chemical library),
is readily
miscible with water and
cell culture media, and has a high boiling point (this improves the accuracy of test compound concentrations by reducing room temperature evaporation).
One limitation with DMSO is that it can affect
cell line growth and viability, with low DMSO concentrations sometimes stimulating cell growth, and high DMSO concentrations sometimes inhibiting or killing cells.
DMSO is used as a vehicle in ''
in vivo
Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and p ...
'' studies of test compounds too. It has, for example, been employed as a co-solvent to assist absorption of the
flavonol glycoside Icariin in the
nematode worm ''
Caenorhabditis elegans''.
As with its use in ''in vitro'' studies, DMSO has some limitations in
animal models.
Pleiotropic effects can occur and, if DMSO control groups are not carefully planned, then solvent effects can falsely be attributed to the prospective drug.
For example, even a very low dose of DMSO has a powerful protective effect against
paracetamol (acetaminophen)-induced liver injury in mice.
In addition to the above, 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). DMSO is an effective
paint stripper too, being safer than many of the others such as
nitromethane and
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible wit ...
.
Biology
DMSO is used in
polymerase chain reaction
The polymerase chain reaction (PCR) is a method widely used to rapidly make millions to billions of copies (complete or partial) of a specific DNA sample, allowing scientists to take a very small sample of DNA and amplify it (or a part of it) ...
(PCR) to inhibit
secondary structures
Secondary may refer to: Science and nature
* Secondary emission, of particles
** Secondary electrons, electrons generated as ionization products
* The secondary winding, or the electrical or electronic circuit connected to the secondary winding i ...
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 in a PCR is applicable for supercoiled plasmids (to relax before amplification) or DNA templates with high
GC-content (to decrease
thermostability
In materials science and molecular biology, thermostability is the ability of a substance to resist irreversible change in its chemical or physical structure, often by resisting decomposition or polymerization, at a high relative temperatu ...
). For example, 10% final concentration of DMSO in the PCR mixture with Phusion decreases primer annealing temperature (i.e. primer melting temperature) by .
It is well known as a reversible cell cycle arrester at phase G1 of human lymphoid cells.
DMSO may also be used as a
cryoprotectant
A cryoprotectant is a substance used to protect biological tissue from freezing damage (i.e. that due to ice formation). Arctic and Antarctic insects, fish and amphibians create cryoprotectants ( antifreeze compounds and antifreeze proteins) in ...
, added to cell media to reduce ice formation and thereby prevent cell death during the freezing process. Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at or stored in
liquid nitrogen safely.
In cell culture, DMSO is used to induce differentiation of P19 embryonic carcinoma cells into cardiomyocytes and skeletal muscle cells.
Medicine
Use of DMSO in medicine dates from around 1963, when an
Oregon Health & Science University
Oregon Health & Science University (OHSU) is a
public research university focusing primarily on health sciences with a main campus, including two hospitals, in Portland, Oregon. The institution was founded in 1887 as the 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 medicine, DMSO is predominantly used as a topical
analgesic, a vehicle for topical application of pharmaceuticals, as an
anti-inflammatory, and an
antioxidant
Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubrica ...
. Because DMSO increases the rate of absorption of some compounds through
biological tissues, including
skin
Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation.
Other animal coverings, such as the arthropod exoskeleton, have different ...
, it is used in some
transdermal drug delivery systems. Its effect may be enhanced with the addition of
EDTA. It is frequently compounded with antifungal medications, enabling them to penetrate not just skin but also toenails and fingernails.
DMSO has been examined for the treatment of numerous conditions and ailments, but the U.S.
Food and Drug Administration
The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
(FDA) has approved its use only for the symptomatic relief of patients with
interstitial cystitis. A 1978 study concluded that DMSO brought
significant relief to the majority of the 213 patients with inflammatory
genitourinary disorders that were studied. 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.
In
interventional radiology
Interventional radiology (IR) is a medical specialty that performs various minimally-invasive procedures using medical imaging guidance, such as x-ray fluoroscopy, computed tomography, magnetic resonance imaging, or ultrasound. IR performs b ...
, DMSO is used as a solvent for
ethylene vinyl alcohol
Ethylene vinyl alcohol (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 ethyle ...
in the
Onyx liquid embolic agent, which is used in
embolization, the therapeutic occlusion of blood vessels.
In
cryobiology
Cryobiology is the branch of biology that studies the effects of low temperatures on living things within Earth's cryosphere or in science. The word cryobiology is derived from the Greek words κρῧος ryos "cold", βίος ios "life", and λ� ...
DMSO has been used as a
cryoprotectant
A cryoprotectant is a substance used to protect biological tissue from freezing damage (i.e. that due to ice formation). Arctic and Antarctic insects, fish and amphibians create cryoprotectants ( antifreeze compounds and antifreeze proteins) in ...
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, 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 an
autologous bone marrow transplant the DMSO is re-infused along with the patient's own
hematopoietic stem cells.
DMSO is metabolized by
disproportionation
In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. More generally, the term can ...
to
dimethyl sulfide and
dimethyl 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 borne
halitosis
Bad breath, also known as halitosis, is a symptom in which a noticeably unpleasant breath odour is present. It can result in anxiety among those affected. It is also associated with depression and symptoms of obsessive compulsive disorder.
...
symptom.
Alternative medicine
DMSO is marketed as an
alternative medicine. Its popularity as an alternative cure is stated to stem from a ''
60 Minutes'' documentary in 1980 featuring an early proponent.
However, DMSO is an ingredient in some products listed by the U.S. FDA as fake cancer cures
and the FDA has had a running battle with distributors.
One such distributor is Mildred Miller, who promoted DMSO for a variety of disorders and was consequently convicted of
Medicare fraud.
The use of DMSO as an alternative treatment for cancer is of particular concern, as it has been shown to interfere with a variety of
chemotherapy
Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemother ...
drugs, including
cisplatin,
carboplatin
Carboplatin, sold under the trade name Paraplatin among others, is a chemotherapy medication used to treat a number of forms of cancer. This includes ovarian cancer, lung cancer, head and neck cancer, brain cancer, and neuroblastoma. It is used ...
, and
oxaliplatin. There is insufficient evidence to support the hypothesis that DMSO has any effect,
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 the
usual disclaimer.
Veterinary medicine
DMSO is commonly used in veterinary medicine as a
liniment
Liniment (from la, linere, meaning "to anoint"), also called embrocation and heat rub, is a medicated topical preparation for application to the skin. Some liniments have viscosity similar to that of water; others are lotion or balm; still oth ...
for
horse
The horse (''Equus ferus caballus'') is a domesticated, one-toed, hoofed mammal. It belongs to the taxonomic family Equidae and is one of two extant subspecies of ''Equus ferus''. The horse has evolved over the past 45 to 55 million yea ...
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.
Taste
The perceived garlic taste upon skin contact with DMSO may be due to
nonolfactory activation of
TRPA1 receptors in
trigeminal ganglia
A trigeminal ganglion (or Gasserian ganglion, or semilunar ganglion, or Gasser's ganglion) is the sensory ganglion at the base of each of the two trigeminal nerves (CN V), occupying a cavity ( Meckel's cave) in the dura mater, covering the trigem ...
. Unlike
dimethyl
Ethane ( , ) is an organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petr ...
and
diallyl disulfides (which have odors resembling garlic),
mono-
Numeral or number prefixes are prefixes derived from numerals or occasionally other numbers. In English and many other languages, they are used to coin numerous series of words. For example:
* unicycle, bicycle, tricycle (1-cycle, 2-cycle, 3-cy ...
and
tri-
Numeral or number prefixes are prefixes derived from numerals or occasionally other numbers. In English and many other languages, they are used to coin numerous series of words. For example:
* unicycle, bicycle, tricycle (1-cycle, 2-cycle, 3-c ...
sulfides (which typically have foul odors), and similar odiferous sulfur compounds, the pure chemical DMSO is odorless.
Safety
Toxicity
DMSO is a non-toxic solvent with a
median lethal dose higher than ethanol (DMSO: LD
50, oral, rat, 14,500 mg/kg; ethanol: LD
50, oral, rat, 7,060 mg/kg).
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. 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.
In Australia, was listed as a
Schedule 4 (S4) Drug, and a company has been prosecuted for adding it to products as a preservative. However, since 2018 it is now
Schedule 6 (S6) in certain circumstances, including cosmetic preparations
Because DMSO easily penetrates the
skin
Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation.
Other animal coverings, such as the arthropod exoskeleton, have different ...
, substances dissolved in DMSO may be quickly absorbed.
Glove selection is important when working with DMSO.
Butyl rubber
Butyl rubber, sometimes just called "butyl", is a synthetic rubber, a copolymer of isobutylene with isoprene. The abbreviation IIR stands for isobutylene isoprene rubber. Polyisobutylene, also known as "PIB" or polyisobutene, (C4H8)n, is the ...
,
fluoroelastomer {{refimprove, date=June 2008
A fluoroelastomer is a fluorocarbon-based synthetic rubber. Fluroelastomers generally have wide chemical resistance.
Composition
Several compositions of fluoroelastomers exist including FKM (by ASTM D1418 standard, equi ...
,
neoprene, or thick (15
mil / 0.4
mm)
latex
Latex is an emulsion (stable dispersion) of polymer microparticles in water. Latexes are found in nature, but synthetic latexes are common as well.
In nature, latex is found as a milky fluid found in 10% of all flowering plants (angiosperms ...
gloves are recommended.
Nitrile gloves, which are very commonly used in chemical laboratories, may protect from brief contact but have been found to degrade rapidly with exposure to DMSO.
On September 9, 1965, ''
The Wall Street Journal
''The Wall Street Journal'' is an American business-focused, international daily newspaper based in New York City, with international editions also available in Chinese and Japanese. The ''Journal'', along with its Asian editions, is published ...
'' 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
Clinical research is a branch of healthcare science that determines the safety and effectiveness ( efficacy) of medications, devices, diagnostic products and treatment regimens intended for human use. These may be used for prevention, treat ...
using DMSO was halted and did not begin again until the
National Academy of Sciences (NAS) published findings in favor of DMSO in 1972.
[https://www.fda.gov/ForIndustry/ImportProgram/ImportAlerts/ucm162294.htm ] In 1978, the US FDA approved DMSO for treating
interstitial 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 following
traumatic brain injury.
DMSO exposure to developing mouse brains can produce brain degeneration. This
neurotoxicity could be detected at
doses as low as 0.3mL/kg, a level exceeded in children exposed to DMSO during
bone marrow transplant.
DMSO disposed into
sewers can also cause odor problems in municipal effluents: waste water
bacteria
Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were am ...
transform DMSO under
hypoxic (anoxic) conditions into
dimethyl sulfide (DMS) that has a strong disagreeable odor, similar to rotten cabbage. However, chemically pure DMSO is odorless because of the lack of C-S-C (
sulfide
Sulfide (British English also sulphide) is an inorganic anion of sulfur with the chemical formula S2− or a compound containing one or more S2− ions. Solutions of sulfide salts are corrosive. ''Sulfide'' also refers to chemical compounds la ...
) and C-S-H (
mercaptan) linkages. Deodorization of DMSO is achieved by removing the odorous impurities it contains.
Explosion hazard
Dimethyl sulfoxide can produce an explosive reaction when exposed to
acyl chlorides; at a low temperature, this reaction produces the
oxidant
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...
for
Swern 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.
[ CD-ROM: ]
See also
* Varying oxidation of sulfur
**
Dimethyl sulfide (DMS), the corresponding sulfide, also produced by marine phytoplankton and emitted to the oceanic atmosphere where it is oxidized to DMSO, SO
2 and sulfate
** Dimethyl sulfone, commonly known as
methylsulfonylmethane (MSM), a related chemical often marketed as a dietary supplement
*Related compounds with methyl on oxygen
**
Dimethyl sulfite, the corresponding sulfite
**
Dimethyl sulfate (also DMS), the corresponding sulfate: a
mutagenic alkylating
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 (or their equivalents). Alkylating agents are reagents for effectin ...
compound
**
Methyl methanesulfonate, another methylating agent
*
Gloria Ramirez, also known as the "Toxic Woman"
References
External links
*
Dimethyl Sulfoxide Information Center
{{DEFAULTSORT:Dimethyl Sulfoxide
Solvents
Sulfoxides
Foul-smelling chemicals