Dimethyl sulfoxide (DMSO) is an
organosulfur compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
. This colorless liquid is the
sulfoxide
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. E ...
most widely used commercially. It is an important
polar aprotic solvent
A polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine groups. In contrast to protic solvents, these solvents do not serve as proton donors in hydrogen bonding
In chemistry, a hy ...
that dissolves both
polar and nonpolar compounds and is
miscible
Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). Such substances are said to be miscible (etymologically ...
in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a
garlic
Garlic (''Allium sativum'') is a species of bulbous flowering plants in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chives, Welsh onion, and Chinese onion. Garlic is native to central and south Asia, str ...
-like taste in the mouth after DMSO is absorbed by skin.
In terms of chemical structure, the molecule has idealized
Cs symmetry
Symmetry () in everyday life refers to a sense of harmonious and beautiful proportion and balance. In mathematics, the term has a more precise definition and is usually used to refer to an object that is Invariant (mathematics), invariant und ...
. 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 corne ...
consistent with other three-coordinate S(IV) compounds, with a
nonbonded electron pair on the approximately
tetrahedral
In geometry, a tetrahedron (: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular Face (geometry), faces, six straight Edge (geometry), edges, and four vertex (geometry), vertices. The tet ...
sulfur atom.
Synthesis and production
Dimethyl sulfoxide was first synthesized in 1866 by the Russian scientist
Alexander Zaytsev, who reported his findings in 1867.
Its modern use as an industrial solvent began through popularization by Thor Smedslund at the Stepan Chemical Company. Dimethyl sulfoxide is produced industrially from
dimethyl sulfide
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula . It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at . It is a component of the smell produc ...
, a by-product of the
Kraft process
The kraft process (also known as kraft pulping or sulfate process) is a process for conversion of wood into wood pulp, which consists of almost pure cellulose fibres, the main component of paper. The kraft process involves treatment of wood chip ...
, by oxidation with oxygen or
nitrogen dioxide
Nitrogen dioxide is a chemical compound with the formula . One of several nitrogen oxides, nitrogen dioxide is a reddish-brown gas. It is a paramagnetic, bent molecule with C2v point group symmetry. Industrially, is an intermediate in the s ...
.
Reactions
Reactions with electrophiles
The sulfur center in DMSO is
nucleophilic
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they a ...
toward soft
electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively Electric charge, charged, have an ...
s and the oxygen is nucleophilic toward hard electrophiles. With
methyl iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...
it forms
trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide is an organosulfur compound with the chemical formula . It is a sulfoxonium salt derived from dimethylsulfoxide. It is iodide salt of a common sulfoxonium cation. This compound, a colorless solid, is commercially avail ...
, :
:
This salt can be
deprotonated
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.ed ...
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 co ...
to form the
sulfur
Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...
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 ...
:
:
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
Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula . It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature ...
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 co ...
. Stabilization of the resultant
carbanion
In organic chemistry, a carbanion is an anion with a lone pair attached to a tervalent carbon atom. This gives the carbon atom a negative charge.
Formally, a carbanion is the conjugate base of a carbon acid:
:
where B stands for the base (chemist ...
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
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
to form sodium
enolates
In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl () compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds.
Bonding and structure
Enolate anions are electr ...
,
phosphonium salt
In chemistry, the term phosphonium (more obscurely: phosphinium) describes polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, organyl or halogen group). These cations have tetrahedral structures. The salt ...
s to form
Wittig reagent In organic chemistry, Wittig reagents are organophosphorus compounds of the formula R3P=CHR', where R is usually phenyl. They are used to convert ketones and aldehydes to alkenes:
:
Preparation
Because they typically hydrolyze and oxidize readily, ...
s, and
formamidinium salts to form
diaminocarbene
A persistent carbene (also known as stable carbene) is an organic molecule whose natural resonance structure has a carbon atom with octet rule, incomplete octet (a carbene), but does not exhibit the tremendous instability typically associated with ...
s. The dimsyl anion is a potent nucleophile.
Oxidant
In
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
, 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 redox, oxidation of primary and secondary alcohols to aldehydes and ketones, respectively. The oxidant is a combination of dime ...
,
Corey–Kim oxidation and the
Swern oxidation
In organic chemistry, the Swern oxidation also known as Moffatt-Swern, named after Daniel Swern, is a chemical reaction whereby a primary or secondary Alcohol (chemistry), alcohol () is redox, oxidized to an aldehyde () or ketone () using oxalyl ...
. The
Kornblum oxidation is conceptually similar. These methods 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 Substitution (chemistry), substituents attached to sulfur. These organosulfur compounds have t ...
species () where X is a heteroatom attached to oxygen).
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 with a 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 el ...
in
coordination chemistry
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...
. Illustrative is the complex
dichlorotetrakis(dimethyl sulfoxide)ruthenium(II)
Dichlorotetrakis(dimethyl sulfoxide) ruthenium(II) describes coordination compounds with the formula RuCl2(dmso)4, where DMSO is dimethylsulfoxide. Both cis and trans isomers are known, but the cis isomer is more common. The cis isomer is a yell ...
(). In this complex, three DMSO ligands are bonded to
ruthenium
Ruthenium is a chemical element; it has 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 unreactive to most chem ...
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
,
phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
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 (chemistry), redistri ...
, metalloporphyrins, and the dimer
. The donor properties are discussed in the
ECW model
In chemistry, the ECW model is a semi-quantitative model that describes and predicts the strength of Lewis acid–Lewis base interactions. Many chemical reactions can be described as acid–base reactions, so models for such interactions are of pot ...
. 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
A polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine groups. In contrast to protic solvents, these solvents do not serve as proton donors in hydrogen bonding
In chemistry, a hyd ...
and is less toxic than other members of this class, such as
dimethylformamide
Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...
,
dimethylacetamide
Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, althou ...
,
''N''-methyl-2-pyrrolidone, and
hexamethylphosphoramide
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is used as a solvent in organic synthesis.
Structure and reactivity
HMPA is the oxide of tris(dimethyla ...
(HMPA). DMSO is frequently used as a
solvent
A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
for chemical reactions involving salts, most notably
Finkelstein reaction
The Finkelstein reaction, named after the German chemist Hans Finkelstein, is a type of SN2 reaction (substitution nucleophilic bimolecular reaction) that involves the exchange of one halogen atom for another. It is an equilibrium reaction, bu ...
s and other
nucleophilic substitution
In chemistry, a nucleophilic substitution (SN) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile) ...
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
In organic chemistry, a carbanion is an anion with a lone pair attached to a tervalent carbon atom. This gives the carbon atom a negative charge.
Formally, a carbanion is the conjugate base of a carbon acid:
:
where B stands for the base (chemist ...
s. A set of non-aqueous
p''K''a 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 as easily be recovered compared to other solvents, as it is very difficult to remove all traces of DMSO by conventional
rotary evaporation
A rotary evaporator (rotovap) is a device used in chemical laboratories for the efficient and gentle removal of solvents from samples by evaporation. When referenced in the chemistry research literature, description of the use of this technique an ...
. 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.
In its
deuterated form (
DMSO-''d''6), it is a useful solvent for
NMR
Nuclear magnetic resonance (NMR) is a physical phenomenon in which atomic nucleus, nuclei in a strong constant magnetic field are disturbed by a weak oscillating magnetic field (in the near and far field, near field) and respond by producing ...
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
Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance ...
, which leads to an overwhelming H
2O resonance in the
1H-NMR spectrum. It can be mixed with
CDCl3 or
CD2Cl2 for lower viscosity and melting points.
DMSO is used to dissolve test compounds in ''
in vitro
''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
''
drug discovery
In the fields of medicine, biotechnology, and pharmacology, drug discovery is the process by which new candidate medications are discovered.
Historically, drugs were discovered by identifying the active ingredient from traditional remedies or ...
and
drug design
Drug design, often referred to as rational drug design or simply rational design, is the invention, inventive process of finding new medications based on the knowledge of a biological target. The drug is most commonly an organic compound, organi ...
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), a s ...
programs, including
high-throughput screening
High-throughput screening (HTS) is a method for scientific discovery especially used in drug discovery and relevant to the fields of biology, materials science and chemistry. Using robotics, data processing/control software, liquid handling device ...
programs.
This is because it is able to dissolve both
polar
Polar may refer to:
Geography
* Geographical pole, either of the two points on Earth where its axis of rotation intersects its surface
** Polar climate, the climate common in polar regions
** Polar regions of Earth, locations within the polar circ ...
and
nonpolar
In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end.
Polar molecules must contain one or more polar ...
compounds,
can be used to maintain
stock solution
Stocks (also capital stock, or sometimes interchangeably, shares) consist of all the shares by which ownership of a corporation or company is divided. A single share of the stock means fractional ownership of the corporation in proportion t ...
s of test compounds (important when working with a large
chemical library
A chemical library or compound library is a collection of stored chemicals usually used ultimately in high-throughput screening or industrial manufacture. The chemical library can consist in simple terms of a series of stored chemicals. Each chemi ...
),
is readily
miscible
Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). Such substances are said to be miscible (etymologically ...
with water and
cell culture media
Cell most often refers to:
* Cell (biology), the functional basic unit of life
* Cellphone, a phone connected to a cellular network
* Clandestine cell, a penetration-resistant form of a secret or outlawed organization
* Electrochemical cell, a de ...
, 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
An immortalised cell line is a population of cells from a multicellular organism that would normally not proliferate indefinitely but, due to mutation, have evaded normal cellular senescence and instead can keep undergoing division. The cells ...
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, an ...
'' studies of test compounds. It has, for example, been employed as a co-solvent to assist absorption of the
flavonol glycoside icariin
Icariin is a chemical compound classified as a prenylated flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-''O''-diglucoside. The compound has been isolated from several species of plant belonging to the ge ...
in the
nematode
The nematodes ( or ; ; ), roundworms or eelworms constitute the phylum Nematoda. Species in the phylum inhabit a broad range of environments. Most species are free-living, feeding on microorganisms, but many are parasitic. Parasitic worms (h ...
worm ''
Caenorhabditis elegans
''Caenorhabditis elegans'' () is a free-living transparent nematode about 1 mm in length that lives in temperate soil environments. It is the type species of its genus. The name is a Hybrid word, blend of the Greek ''caeno-'' (recent), ''r ...
''.
As with its use in ''in vitro'' studies, DMSO has some limitations in
animal models
A model organism is a non-human species that is extensively studied to understand particular biological phenomena, with the expectation that discoveries made in the model organism will provide insight into the workings of other organisms. Mod ...
.
Pleiotropic
Pleiotropy () is a condition in which a single gene or genetic variant influences multiple phenotypic traits. A gene that has such multiple effects is referred to as a ''pleiotropic gene''. Mutations in pleiotropic genes can impact several trait ...
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
Paracetamol, or acetaminophen, is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol.
Parac ...
(acetaminophen)-induced liver injury in mice.
DMSO finds some 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).
Biology
DMSO is used in the
polymerase chain reaction
The polymerase chain reaction (PCR) is a method widely used to make millions to billions of copies of a specific DNA sample rapidly, allowing scientists to amplify a very small sample of DNA (or a part of it) sufficiently to enable detailed st ...
(PCR) to inhibit
secondary structures in the
DNA template or the
DNA primer
A primer is a short, single-stranded nucleic acid used by all living organisms in the initiation of DNA synthesis. A synthetic primer is a type of oligo, short for oligonucleotide. DNA polymerases (responsible for DNA replication) are only capab ...
s. 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
In molecular biology and genetics, GC-content (or guanine-cytosine content) is the percentage of nitrogenous bases in a DNA or RNA molecule that are either guanine (G) or cytosine (C). This measure indicates the proportion of G and C bases out of ...
(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 temperature.
T ...
). 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 th ...
, 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
Liquid nitrogen (LN2) is nitrogen in a liquid state at cryogenics, low temperature. Liquid nitrogen has a boiling point of about . It is produced industrially by fractional distillation of liquid air. It is a colorless, mobile liquid whose vis ...
safely.
In cell culture, DMSO is used to induce
differentiation of
P19 embryonic carcinoma cell
P19 cells is an embryonic carcinoma cell line derived from an embryo-derived teratocarcinoma in mice. The cell line is pluripotent and can differentiate into cell types of all three germ layers. Also, it is the most characterized embryonic carcinom ...
s into
cardiomyocyte
Cardiac muscle (also called heart muscle or myocardium) is one of three types of vertebrate muscle tissues, the others being skeletal muscle and smooth muscle. It is an involuntary, striated muscle that constitutes the main tissue of the wall of ...
s 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 university, public research university, research university focusing primarily on health sciences with a main campus, including two hospitals, in Portland, Oregon. The institution was founded ...
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
An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...
, a vehicle for topical application of pharmaceuticals, as an
anti-inflammatory
Anti-inflammatory is the property of a substance or treatment that reduces inflammation, fever or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs reduce pain by inhibiting mechan ...
, and an
antioxidant
Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...
. Because DMSO increases the rate of absorption of some compounds through
biological tissue
In biology, tissue is an assembly of similar cells and their extracellular matrix from the same embryonic origin that together carry out a specific function. Tissues occupy a biological organizational level between cells and a complete or ...
s, 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
Transdermal is a route of administration wherein active ingredients are delivered across the skin for systemic distribution. Examples include transdermal patches used for medicine delivery.
The drug is administered in the form of a patch or ointm ...
drug delivery
Drug delivery involves various methods and technologies designed to transport pharmaceutical compounds to their target sites helping therapeutic effect. It involves principles related to drug preparation, route of administration, site-specif ...
systems. Its effect may be enhanced with the addition of
EDTA
Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid, is an aminopolycarboxylic acid with the formula . This white, slightly water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-solubl ...
. 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 List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...
(FDA) has approved its use only for the symptomatic relief of patients with
interstitial cystitis
Interstitial cystitis (IC), a type of bladder pain syndrome (BPS), is chronic pain in the Urinary bladder, bladder and pelvic floor of unknown cause. Symptoms include urinary urgency, feeling the need to urinate right away, urinary frequency, ...
. A 1978 study concluded that DMSO brought
significant relief to the majority of the 213 patients with inflammatory
genitourinary
The genitourinary system, or urogenital system, are the sex organs of the reproductive system and the organs of the urinary system. These are grouped together because of their proximity to each other, their common embryological origin and the us ...
disorders that were studied.
In 2009, the first to obtain FDA approval for topical DMSO usage was PENNSAID
®, which contains diclofenac in a carrier with 45.5% DMSO
Each 1 mL of TDiclo contains 16.05 mg diclofenac sodium. TDiclo solution also contains 45.5% dimethyl sulfoxide (DMSO) vehicle, which can result in enhanced penetration of active drug through the skin.
The most common adverse event reported was dry skin at the application site (25.3% of patients), followed by contact dermatitis (13.0%)
In
interventional radiology
Interventional radiology (IR) is a medical specialty that performs various minimally-invasive procedures using medical imaging guidance, such as Fluoroscopy, x-ray fluoroscopy, CT scan, computed tomography, magnetic resonance imaging, or ultraso ...
, 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 ethy ...
in the
Onyx
Onyx is a typically black-and-white banded variety of agate, a silicate mineral. The bands can also be monochromatic with alternating light and dark bands. ''Sardonyx'' is a variety with red to brown bands alternated with black or white bands. ...
liquid embolic agent, which is used in
embolization
Embolization refers to the passage and lodging of an embolus within the bloodstream. It may be of natural origin ( pathological), in which sense it is also called embolism, for example a pulmonary embolism; or it may be artificially induced ...
, 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 th ...
and is still an important constituent of cryoprotectant
vitrification
Vitrification (, via French ') is the full or partial transformation of a substance into a glass, that is to say, a non- crystalline or amorphous solid. Glasses differ from liquids structurally and glasses possess a higher degree of connectivity ...
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
Embryonic stem cells (ESCs) are Cell potency#Pluripotency, pluripotent stem cells derived from the inner cell mass of a blastocyst, an early-stage pre-Implantation (human embryo), implantation embryo. Human embryos reach the blastocyst stage 4� ...
and
hematopoietic stem cell
Hematopoietic stem cells (HSCs) are the stem cells that give rise to other blood cells. This process is called haematopoiesis. In vertebrates, the first definitive HSCs arise from the ventral endothelial wall of the embryonic aorta within the ...
s, which are often frozen in a mixture of 10% DMSO, a freezing medium, and 30%
fetal bovine serum
Fetal bovine serum (FBS) is the most widely used serum-supplement for the ''in vitro'' cell culture of eukaryotic cells. It is commonly utilized in biomedical research, pharmaceutical development, and biomanufacturing due to its ability to suppo ...
. In the cryogenic freezing of heteroploid cell lines (
MDCK
Madin-Darby canine kidney (MDCK) cells are a model mammalian cell line used in biomedical research. MDCK cells are used for a wide variety of cell biology studies including cell polarity, cell-cell adhesions (termed adherens junctions), collectiv ...
,
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
Autotransplantation is the transplantation of organs, tissues, or even particular proteins from one part of the body to another in the same person ('' auto-'' meaning "self" in Greek).
The autologous tissue (also called autogenous, autogenei ...
bone marrow transplant
Hematopoietic stem-cell transplantation (HSCT) is the transplantation of multipotent hematopoietic stem cells, usually derived from bone marrow, peripheral blood, or umbilical cord blood, in order to replicate inside a patient and produce a ...
the DMSO is re-infused along with the patient's own
hematopoietic stem cell
Hematopoietic stem cells (HSCs) are the stem cells that give rise to other blood cells. This process is called haematopoiesis. In vertebrates, the first definitive HSCs arise from the ventral endothelial wall of the embryonic aorta within the ...
s.
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 state. The reverse of disproportionatio ...
to
dimethyl sulfide
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula . It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at . It is a component of the smell produc ...
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.
Th ...
symptom.
Alternative medicine
DMSO's popularity as an
alternative medicine
Alternative medicine refers to practices that aim to achieve the healing effects of conventional medicine, but that typically lack biological plausibility, testability, repeatability, or supporting evidence of effectiveness. Such practices are ...
is stated to stem from a March 1980 ''
60 Minutes
''60 Minutes'' is an American television news magazine broadcast on the CBS television network. Debuting in 1968, the program was created by Don Hewitt and Bill Leonard, who distinguished it from other news programs by using a unique style o ...
'' documentary "The Riddle of DMSO"
and April 1980 ''
Time
Time is the continuous progression of existence that occurs in an apparently irreversible process, irreversible succession from the past, through the present, and into the future. It is a component quantity of various measurements used to sequ ...
'' magazine article covering the treatments of ardent DMSO advocate Dr. Stanley Jacob beginning in the 1960s.
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 chemo, sometimes CTX and CTx) is the type of cancer treatment that uses one or more anti-cancer drugs (list of chemotherapeutic agents, chemotherapeutic agents or alkylating agents) in a standard chemotherapy re ...
drugs, including
cisplatin
Cisplatin is a chemical compound with chemical formula, formula ''cis''-. It is a coordination complex of platinum that is used as a chemotherapy medication used to treat a number of cancers. These include testicular cancer, ovarian cancer, c ...
,
carboplatin
Carboplatin, sold under the brand 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 a ...
, and
oxaliplatin
Oxaliplatin, sold under the brand name Eloxatin among others, is a cancer medication (platinum-based antineoplastic class) used to treat colorectal cancer. It is given by intravenous, infusion into a vein.
Common side effects include paresth ...
. 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. 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
In the United States, Medicare fraud is the claiming of Medicare (United States), Medicare health care reimbursement to which the claimant is not entitled. There are many different types of Medicare fraud, all of which have the same goal: to collec ...
.
Veterinary medicine
DMSO is commonly used in veterinary medicine as a
liniment
Liniment (from , meaning "to smear, Anointing, anoint"), also called embrocation and heat rub, is a medicated topical preparation for application to the skin. Some liniments have a viscosity similar to that of water; others are lotion or balm; s ...
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 mi ...
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
Transient receptor potential cation channel, subfamily A, member 1, also known as transient receptor potential ankyrin 1, TRPA1, or The Mustard and Wasabi Receptor, is a protein that in humans is encoded by the ''TRPA1'' (and in mice and rats by ...
receptors in
trigeminal ganglia
The trigeminal ganglion (also known as: Gasserian ganglion, semilunar ganglion, or Gasser's ganglion) is the sensory ganglion of each trigeminal nerve (CN V). The trigeminal ganglion is located within the trigeminal cave (Meckel's cave), a cav ...
. Unlike
dimethyl
Ethane ( , ) is a naturally occurring 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 ...
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:
* triangle, quadrilateral, pentagon, hexagon, oc ...
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:
*triangle, quadrilateral, pentagon, hexagon, octagon ...
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
In toxicology, the median lethal dose, LD50 (abbreviation for " lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose re ...
higher than ethanol (DMSO: LD
50, oral, rat, 14,500 mg/kg; ethanol: LD
50, oral, rat, 7,060 mg/kg).
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.
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 quickly be absorbed.
Glove
A glove is a garment covering the hand, with separate sheaths or openings for each finger including the thumb. Gloves protect and comfort hands against cold or heat, damage by friction, abrasion or chemicals, and disease; or in turn to provide a ...
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 homop ...
,
fluoroelastomer
A fluoroelastomer is a fluorocarbon-based synthetic rubber. Fluoroelastomers generally have wide chemical resistance.
Composition
Several compositions of fluoroelastomers exist including FKM (by ASTM D1418 standard, equivalent to FPM by ISO/DIN ...
,
neoprene
Neoprene (also polychloroprene) is a family of synthetic rubbers that are produced by polymerization of chloroprene.Werner Obrecht, Jean-Pierre Lambert, Michael Happ, Christiane Oppenheimer-Stix, John Dunn and Ralf Krüger "Rubber, 4. Emulsion Rub ...
, or thick (15
mil / 0.4
mm)
latex
Latex is an emulsion (stable dispersion) of polymer microparticles in water. Latices are found in nature, but synthetic latices are common as well.
In nature, latex is found as a wikt:milky, milky fluid, which is present in 10% of all floweri ...
gloves are recommended.
Nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...
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.
Toxicology study
Considering its wide use, especially for cryopreservation and ''in vitro'' assays, we evaluated biological effect of DMSO using these technological innovations. We exposed 3D cardiac and hepatic microtissues to medium with or without 0.1% DMSO and analyzed the transcriptome, proteome and DNA methylation profiles. In both tissue types, transcriptome analysis detected >2000 differentially expressed genes affecting similar biological processes, thereby indicating consistent cross-organ actions of DMSO.
There are
transcriptional
Transcription is the process of copying a segment of DNA into RNA for the purpose of gene expression. Some segments of DNA are transcribed into RNA molecules that can encode proteins, called messenger RNA (mRNA). Other segments of DNA are transc ...
,
translational and
epigenetic
In biology, epigenetics is the study of changes in gene expression that happen without changes to the DNA sequence. The Greek prefix ''epi-'' (ἐπι- "over, outside of, around") in ''epigenetics'' implies features that are "on top of" or "in ...
changes caused by low concentration DMSO, despite the lack of acute toxicity, indicating potential long term effects.
Regulation
In Australia, it is listed as a
Schedule 4 (S4) Drug, and a company has been prosecuted for adding it to products as a preservative.
Clinical safety
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.
On September 9, 1965, ''
The Wall Street Journal
''The Wall Street Journal'' (''WSJ''), also referred to simply as the ''Journal,'' is an American newspaper based in New York City. The newspaper provides extensive coverage of news, especially business and finance. It operates on a subscriptio ...
'' 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 medical research that involves people and aims to determine the effectiveness (efficacy) and safety of medications, devices, diagnostic products, and treatment regimens intended for improving human health. The ...
using DMSO was halted and did not begin again until the
National Academy of Sciences
The National Academy of Sciences (NAS) is a United States nonprofit, NGO, non-governmental organization. NAS is part of the National Academies of Sciences, Engineering, and Medicine, along with the National Academy of Engineering (NAE) and the ...
(NAS) published findings in favor of DMSO in 1972.
[fda.gov](_blank)
In 1978, the US FDA approved DMSO for treating
interstitial cystitis
Interstitial cystitis (IC), a type of bladder pain syndrome (BPS), is chronic pain in the Urinary bladder, bladder and pelvic floor of unknown cause. Symptoms include urinary urgency, feeling the need to urinate right away, urinary frequency, ...
. 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
A traumatic brain injury (TBI), also known as an intracranial injury, is an injury to the brain caused by an external force. TBI can be classified based on severity ranging from mild traumatic brain injury (mTBI/concussion) to severe traumati ...
.
DMSO exposure to developing mouse brains can produce brain degeneration. This
neurotoxicity
Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifical ...
could be detected at
dose
Dose or Dosage may refer to:
Music
* ''Dose'' (Gov't Mule album), 1998
* ''Dose'' (Latin Playboys album)
* ''Dosage'' (album), by the band Collective Soul
* "Dose" (song), a 2018 song by Ciara
* "Dose", song by Filter from the album '' Short ...
s as low as 0.3mL/kg, a level exceeded in children exposed to DMSO during
bone marrow transplant
Hematopoietic stem-cell transplantation (HSCT) is the transplantation of multipotent hematopoietic stem cells, usually derived from bone marrow, peripheral blood, or umbilical cord blood, in order to replicate inside a patient and produce a ...
.
Odor problem
DMSO disposed into
sewers can cause odor problems in municipal effluents: waste water
bacteria
Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
transform DMSO under
hypoxic
Hypoxia means a lower than normal level of oxygen, and may refer to:
Reduced or insufficient oxygen
* Hypoxia (environmental), abnormally low oxygen content of a specific environment
** Hypoxia in fish, responses of fish to hypoxia
* Hypoxia (medi ...
(anoxic) conditions into
dimethyl sulfide
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula . It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at . It is a component of the smell produc ...
(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 (also sulphide in British English) 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 large families o ...
) and C-S-H (
mercaptan
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...
) 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 chloride
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...
s; 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 "Electron acceptor, accepts"/"receives" an electron from a (called the , , or ''electr ...
for
Swern oxidation
In organic chemistry, the Swern oxidation also known as Moffatt-Swern, named after Daniel Swern, is a chemical reaction whereby a primary or secondary Alcohol (chemistry), alcohol () is redox, oxidized to an aldehyde () or ketone () using oxalyl ...
.
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
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula . It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at . It is a component of the smell produc ...
(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
Dimethyl sulfone (DMSO2) is an organosulfur compound with the formula . It is also known by several other names including methyl sulfone and (especially in alternative medicine) methylsulfonylmethane (MSM). This colorless solid features the sulfo ...
(MSM), a related chemical often marketed as a dietary supplement
* Related compounds with methyl on oxygen
**
Dimethyl sulfite
Ethane ( , ) is a naturally occurring 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 ...
, the corresponding sulfite
**
Dimethyl sulfate
Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agen ...
(also DMS), the corresponding sulfate: a
mutagenic
In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in ...
alkylating Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 effecting al ...
compound
**
Methyl methanesulfonate
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated ...
, another methylating agent
*
Death of Gloria Ramirez, where DMSO taken by a terminally ill patient caused medical staff to fall ill
References
External links
*
Dimethyl Sulfoxide Information Center
{{DEFAULTSORT:Dimethyl Sulfoxide
Solvents
Sulfoxides
Foul-smelling chemicals
Methyl compounds