DIMETHYL SULFOXIDE

DIMETHYL SULFOXIDE

DIMETHYL SULFOXIDE

Dimethyl sulfoxide, also called DMSO, is a dipolar aprotic solvent. 
Dimethyl sulfoxide or DMSO, a dipolar aprotic solvent with high flash- and boiling-point, possesses outstanding properties of miscibility with polar and non-polar solvents. 
DMSO is manufactured using black liquor, a byproductof paper mills. DMSO is used in a wide range of applications, such aspharmaceuticals, agrochemicals, and fine chemicals. 
With ongoing research and development to bolster the use of DMSO in the pharmaceutical sector, it’s expected that global consumption will witness an increase during the forecast period, 2016-2026. 
Moreover, owing to its nontoxic and biodegradable properties, its use in the agrochemicals sector is also expected towitness steady growth during the forecast period.

Dimethyl sulfoxide has high flash point as well as high boiling point. In addition, Dimethyl sulfoxide possesses excellent miscibility with polar and non-polar solvents. 
Dimethyl sulfoxide is commonly produced by using black liquor, a byproduct of paper mills.
Dimethyl sulfoxide is commonly employed in applications such as pharmaceuticals, agrochemicals, and fine chemicals
Based on grade, the global dimethyl sulfoxide market can be segmented into reagent grade, technical grade, spectrophotometric, and anhydrous. 
Reagent-grade dimethyl sulfoxide is primarily used as a solvent for non-spectrophotometric methods of analysis. 
Also, it can be used as a solvent for gas chromatography. 
On the other hand, technical-grade dimethyl sulfoxide is often used as a solvent in cleaning and paint stripping.
In terms of application, the global dimethyl sulfoxide market can be divided into active pharmaceutical ingredients & intermediates, paint stripping, polymer processing, agrichemicals, and others. 
As a cleaning solution, DMSO is often used for removal of organic materials from production lines and manufacturing equipment. 
Owing to high solubility of DMSO in polymers, it is used in reaction solvents and in polymer processing and cleanup.
Non-toxic nature of DMSO aids in the formulation of hazardous solvents in paint stripping formulations.
Due to its high solvency, Dimethyl sulfoxide is employed in the manufacture of highly concentrated formulations.  
DMSO is used as a solvent for a wide range of active ingredients used in herbicides, insecticides, and fungicides such as propiconazole, pinoxaden, pyroxasulfone, mentaconazole, imazethaphyr, imazamethabenz-methyl, trubupirimphos, cyfluthrin, glysophate, and imidacloprid.

Dimethyl sulfoxide (DMSO) is a highly polar and water miscible organic liquid. It is essentially odorless and has a low level of toxicity.
Dimethyl sulfoxide (DMSO) is a highly polar and water miscible organic liquid. Due to its powerful solvent, it is named as \”Universal solvent\”.

Dimethyl sulfoxide has many properties, such as powerful solvent, high flash point and boiling point, excellent toxicological and eco toxicological profile, recyclable, biodegradable and low odor, so it is wildly used in pharmaceutical, electronic and chemical fields.

Dimethylsulfoxide (DMSO) is a highly polar and water miscible organic liquid, with an exceptionaly low level of toxicity. 

Dimethyl Sulfoxide is a highly polar organic liquid that is used widely as a chemical solvent and a free radical scavenger. 

Dimethyl Sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation. 
Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. 

Dimethyl Sulfoxide is also used to protect cells and tissue during cryopreservation and has been used to treat extravasation damage caused by anthracycline-based chemotherapy.

DMSO is a clear, transparent liquid. DMSO is high polar and high boiling solvent completely miscible with water. 
It has a low toxicity profile compared to the majority of competing solvents (like n-methyl pyrrolidone, NMP). 
DMSO is used as solvent both in synthesis and formulation in many different applications: pharmaceuticals intermediate, agrochemicals, polymers, refineries, electronics, antifreeze, fibres and extraction.

Attributes of DMSO such as its amphiphilic nature, high solvency, miscibility, and relatively low toxicity at dilute concentrations make it an ideal solvent in a wide range of applications including active pharmaceutical ingredients and intermediates, paint stripping formulations, polymer processing, and agrochemicals
High solvency power of DMSO is expected to drive the demand for DMSO in the agrochemical sector. 
In addition, rising demand for non-toxic solvents is likely to boost the global DMSO market during the forecast period. 
Furthermore, increasing need for improving crop productivity coupled with growing support by governments by offering subsidies and rebates to agriculturists is expected to drive the demand for fertilizers and herbicides worldwide. 
This, in turn, is projected to boost the demand for DMSO in the near future.

Global Dimethyl Sulfoxide Market, by Application

Active Pharmaceutical Ingredients & Intermediates
Paint Stripping
Polymer Processing
Agrichemicals
Others

Product Name: DMSO
Dimethyl sulfoxide
CAS No.67-68-5
EINECS:200-664-3

Typical Properties    
Appearance: Colorless liquid
Specific Gravity(At 25°C): Not less than 1.093
Purity(GC area %): Not less than 99.9%
Water Content(KF): Not more than 0.1%
Reducing Materials (As Formaldehyde): Not more than 0.01%
pH:6～8

End Uses:    
Removers and Cleaners
Organic synthesis solvents
Polymerized yarn solvents

Dimethyl Sulfoxide
DMSO is the widely accepted solvent of choice for storage of compounds, despite the hygroscopic nature of the solvent, which can lead to stability issues.

Dimethyl sulfoxide appears as a clear liquid, essentially odorless. Closed cup flash point 192°F. Vapors are heavier than air. Contact with the skin may cause stinging and burning and lead to an odor of garlic on the breath. An excellent solvent that can transport toxic solutes through the skin. High vapor concentrations may cause headache, dizziness, and sedation.

EC / List no.: 200-664-3
CAS no.: 67-68-5
Mol. formula: C2H6OS

Dimethyl sulfoxide is a 2-carbon sulfoxide in which the sulfur atom has two methyl substituents. 
It has a role as a polar aprotic solvent, a radical scavenger, a non-narcotic analgesic, an antidote, a MRI contrast agent, an Escherichia coli metabolite and an alkylating agent. 
It is a sulfoxide and a volatile organic compound.

DMSO (Dimethyl Sulfoxide) is an organosulfur compound with the formula (CH₃)₂SO. It is a colorless liquid and is a powerful solvent. 
It dissolves both polar and non-polar compounds. This property makes the DMSO miscible in a wide range of organic solvents as well as water.

Sigma Aldrich Dimethyl Sulfoxide Lewis Structure
DMSO is a potent solvent because of its highly polar nature. DMSO works with ionic compounds, certain salts, and non-ionic compounds. 
There are some limitations to its use when used with non-polar compounds.

Use DMSO when your application calls for a polar, aprotic solvent that’s easily able to dissolve many substances that have extremely poor solubility in water.

Dimethyl Sulfoxide, DMSO, has a a central sulfur atom that is bound to two methyl groups through single bonds and an oxygen atom joined through a double bond to the sulfur atom.

IUPAC Names 
(methanesulfinyl)methane
dimethyl sulfoxide
INNs     Sources
dimethyl sulfoxide    
dimethyli sulfoxidum LINGUA LATINA    
diméthylsulfoxyde Français    
dimetil sulfóxido Español    
Synonyms     
(CH3)2SO    
Dimethyl sulfoxide    
DIMETHYL SULFOXIDE    
dimethyl sulfoxide    
dimethyl sulfur oxide    
dimethyl sulphoxide    
Dimethylsulfoxid Deutsch    
DMSO    KEGG COMPOUND
dmso    IUPAC
methylsulfinylmethane    
S(O)Me2    ChEBI
sulfinylbis(methane)
Dimethyl sulfoxide
Dimethyl sulfoxide
dimethyl sulfoxide
dimethyl sulphoxide
CAS names

Methane, 1,1′-sulfinylbis-
IUPAC names
Dimethyl Sulfoxide
Dimethyl sulfoxide
dimethyl sulfoxide
Dimethyl Sulfoxide
Dimethyl sulfoxide
dimethyl sulfoxide
Dimethyl sulphoxide, anhydrous
Dimethylsulfoxid
Dimethylsulfoxide
DMSO, Methyl Sulfoxide
methanesulfinylmethane
Methylsulfinidemethane
methylsulfinylmethan
methylsulfinylmethane

Trade names
Dimethyl Sulfoxide

DMSO

Enviro-S
Procipient

Other names: DMSO; Methane, sulfinylbis-; Methyl sulfoxide; Demsodrox; Dimexide; Dipirartril-tropico; Dolicur; Dromisol; Durasorb; DMS 70; DMS 90; Hyadur; Infiltrina; Somipront; Sulfinylbismethane; SQ 9453; Dimethyl sulphoxide; (CH3)2SO; A 10846; Deltan; Demasorb; Demavet; Demeso; Dermasorb; Doligur; Domoso; Gamasol 90; M 176; Methylsulfinylmethane; Rimso 50; Syntexan; NSC-763; Topsym; Dimethyl sulfur oxide; Herpid; Kemsol; Sclerosol; Sulfoxide, dimethyl; Methane, 1,1′-sulfinylbis-; DMSO (methyl sulfoxide); Sulphinylbis methane

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (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. 
Dimethyl sulfoxide has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after contact with the skin.

In terms of chemical structure, the molecule has idealized Cs symmetry. 
It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom.

IUPAC name: Dimethyl sulfoxide
Systematic IUPAC name
(Methanesulfinyl)methane (substitutive)
Dimethyl(oxido)sulfur (additive)

Other names
Methylsulfinylmethane
Methyl sulfoxide

CAS Number: 67-68-5 

Dimethyl sulfoxide appears as a clear liquid, essentially odorless. Closed cup flash point 192°F. Vapors are heavier than air. Contact with the skin may cause stinging and burning and lead to an odor of garlic on the breath. An excellent solvent that can transport toxic solutes through the skin. High vapor concentrations may cause headache, dizziness, and sedation.

dimethyl sulfoxide
DMSO
67-68-5
Methylsulfinylmethane
Dimethylsulfoxide
Dimethyl sulphoxide
Methane, sulfinylbis-
Demsodrox
Demasorb
Demavet
Dimexide
Domoso
Dromisol
Durasorb
Infiltrina
Somipront
Syntexan
Deltan
Demeso
Dolicur
Hyadur
sulfinylbismethane
Dimethyl sulfur oxide
Dermasorb
Dipirartril-tropico
Doligur
Kemsol
Topsym
Gamasol 90
Sulfinylbis(methane)
Dimethylsulphoxide
Sclerosol
Rimso-50
Dimethylsulfoxid
Dimethylsulfoxyde
Rimso 50
SQ 9453
NSC-763
Caswell No. 381
Dimetil sulfoxido
Dimethyli sulfoxidum
CCRIS 943
Methane, 1,1′-sulfinylbis-
(methylsulfinyl)methane
methylsulfoxide
(CH3)2SO
DMS-90
NSC 763
A 10846
Methyl sulphoxide
dimethyl-sulfoxide
S(O)Me2
M 176
UNII-YOW8V9698H
MFCD00002089
EPA Pesticide Chemical Code 000177
DMS 70
DMS 90
AI3-26477
CHEMBL504
NSC763
YOW8V9698H
Dimethyl sulfoxide, HPLC Grade
CHEBI:28262
SQ-9453
Dimethyl sulfoxide, 99%
Sulfinylbis-methane
Topsym (rescinded)
Rimso-5
Domoso (Veterinary)
Methyl sulfoxide, 99.7%, pure
Dimexidum
sulfinyldimethane
Dimetilsolfossido
Dimetilsolfossido [DCIT]
Dimethyl sulpoxide
Methyl sulfoxide, 99.8+%, for HPLC
Methyl sulfoxide, 99.8+%, extra pure
HSDB 80
Methyl sulfoxide, 99.5+%, for analysis
Methyl sulfoxide, 99.9+%, ACS reagent
Sulfoxide, dimethyl
methanesulfinylmethane
DMS-70
Dimethylsulfoxyde [INN-French]
Dimetil sulfoxido [INN-Spanish]
(methanesulfinyl)methane
Dimethyli sulfoxidum [INN-Latin]
Methyl sulfoxide, 99.8+%, for peptide synthesis
EINECS 200-664-3
Methyl sulfoxide, 99.7+%, Extra Dry, AcroSeal(R)
C2H6OS
Diluent
dimethysulfoxide
dimethlysulfoxide
dimethvlsulfoxide
dimethyisulfoxide
dimethylsulphoxid
dimethy sulfoxide
dimetyl sulfoxide
dimethyisulphoxide
Methyl sulfoxide, 99.7+%, Extra Dry over Molecular Sieve, AcroSeal(R)
dimethyl sulfoxyde
dimethyl-sulfoxyde
dimethyl suiphoxide
dimethyl-sulphoxide
dirnethyl sulfoxide
Dimethyl sulfoxixde
methylsulfmylmethane
dimethyl sulf oxide
Sulfinyl bis(methane)
2-Thiapropane2-oxide
Dimethyl sulfoxide [USAN:USP:INN:BAN]
DMSO, sterile filtered
dimethylsulfoxide solution
Methyl sulfoxide (8CI)
Rimso-50 (TN)
Dimethyl sulfoxide(DMSO)
DMSO (Sterile-filtered)
DMSO, Dimethyl Sulfoxide
DSSTox_CID_1735
Dimethyl sulfoxide solution
(DMSO)
DMSO (Dimethyl sulfoxide)
EC 200-664-3
Sulfinylbis-methane (9CI)
ACMC-1BH88
DSSTox_RID_76298
H3C-SO-CH3
BIDD:PXR0182
DSSTox_GSID_21735
Dimethyl sulfoxide, >=99%
Dimethyl sulfoxide, anhydrous
Dimethyl sulfoxide, for HPLC
Methane, sulfinylbis- (9CI)
WLN: OS1&1
Dimethyl sulfoxide, >=99.5%
Dimethyl sulfoxide, PCR Reagent
DTXSID2021735
Dimethyl sulfoxide, ACS reagent
Methyl sulfoxide, >=99%, FG
Dimethyl sulfoxide, p.a., 99%
Dimethyl sulfoxide, LR, >=99%
Pharmakon1600-01506122
Dimethyl sulfoxide (JAN/USP/INN)
Dimethyl sulfoxide, AR, >=99.5%
(methanesulfinyl)methanedimethyl sulfoxide
Dimethyl sulfoxide, for molecular biology

Dimethylsulfoxide (DMSO)  – chemical substance with the formula – (CH3)2SO . 

Dimethylsulfoxide (DMSO) is colorless, odorless liquid with a specific sweetish taste (insufficiently pure product has a characteristic smell of dimethyl sulfide ). 
Dimethylsulfoxide is an important bipolar aprotic solvent . Dimethylsulfoxide is widely used in various fields of chemistry , as well as as a medicine .
EC / List no.: 200-664-3
CAS no.: 67-68-5
Mol. formula: C2H6OS

Systematic name: dimethyl sulfoxide
Abbreviations:    DMSO, DMSO
Chem. formula:    C 2 H 6 OS
Physical properties
condition: liquid
Molar mass: 78.13 g / mol
Density: 1.1004 g / cm³
Dynamic viscosity: 0.001996 Pa s
Thermal properties
Temperature
 •  melting: 18.5 ° C
 •  boiling: 189 ° C
Chemical properties

Solubility
 • in water: unlimited
 • in ethanol:unlimited
 • in benzene: unlimited
 • in chloroform: unlimited
It was first synthesized in 1866 by the Russian chemist Alexander Zaitsev by oxidizing dimethyl sulfide with nitric acid . Over the next few decades, studies of the properties of this compound were not systematic. But it was actively used during the First World War in the hospitals of the Russian army in the treatment of injuries, fractures, wounds. Non-toxicity and non-cumulativeness in the body contributed well to this.

Interest in dimethyl sulfoxide in the West increased greatly after its unique dissolving ability was discovered in 1958 . In 1960, industrial production of dimethyl sulfoxide began. After that, the number of publications devoted to the study of the properties of DMSO increased dramatically.

Synthesis and production
It was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867.[5] Dimethyl sulfoxide is produced industrially from dimethyl sulfide, a by-product of the Kraft process, by oxidation with oxygen or nitrogen dioxide.[6]

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, [(CH3)3SO]I:

(CH3)2SO + CH3I → [(CH3)3SO]I
This salt can be deprotonated with sodium hydride to form the sulfur ylide:

[(CH3)3SO]I + NaH → (CH3)2S(CH2)O + NaI + H2
Acidity
The methyl groups of DMSO are only weakly acidic, with a pKa = 35. 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. 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,[7] as illustrated by the Pfitzner–Moffatt oxidation and the Swern oxidation.[8]

Ligand and Lewis base
Related to its ability to dissolve many salts, DMSO is a common ligand in coordination chemistry.[9] Illustrative is the complex dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) (RuCl2(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 Lewis acids such as I2, phenols, trimethyltin chloride, 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

Solvent

Distillation of DMSO requires a partial vacuum to achieve a lower boiling point.
DMSO is a polar aprotic solvent and is less toxic than other members of this class, such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and HMPA. DMSO is frequently used as a solvent 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.[12] 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 values (C-H, O-H, S-H and N-H acidities) for thousands of organic compounds have been determined in DMSO solution.[13][14]

Because of its high boiling point, 189 °C (372 °F), 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, 18.5 °C (65.3 °F), means that at, or just below, room temperature it is a solid, which can limit its utility in some chemical processes (e.g. crystallization with cooling).

In its deuterated form (DMSO-d6), 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-d6 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 or CD2Cl2 for lower viscosity and melting points.

DMSO is used as a solvent in in vitro and in vivo drug testing.
DMSO is also used to dissolve test compounds in in vitro drug discovery[15][16] and drug design[17] screening programs (including high-throughput screening programs).
This is because it able to dissolve both polar and nonpolar compounds,[15][17] can be used to maintain stock solutions of test compounds (important when working with a large chemical library),[16] 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).[15]

DMSO is used as a vehicle in in vivo 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.[18] As with its use in in vitro studies, DMSO has some limitations in animal models.[19][20] Pleiotropic effects can occur and, if DMSO control groups are not carefully planned, then solvent effects can falsely be attributed to the prospective drug.[19] For example, even a very low dose of DMSO has a powerful protective effect against paracetamol (acetaminophen)-induced liver injury in mice.[20]

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.

Biology
DMSO is used in polymerase chain reaction (PCR) to inhibit secondary structures in the DNA template or the DNA primers. 
It is added to the PCR mix before reacting, where it interferes with the self-complementarity of the DNA, minimizing interfering reactions.

DMSO in a PCR reaction is applicable for supercoiled plasmids (to relax before amplification) or DNA templates with high GC-content (to decrease thermostability). 
For example, 10% final concentration of DMSO in the PCR mixture with Phusion decreases primer annealing temperature (i.e. primer melting temperature) by 5.5–6.0 °C (9.9–10.8 °F).[23]

It is well known as a reversible cell cycle arrester at phase G1 of human lymphoid cells.[24]

DMSO may also be used as a cryoprotectant, 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 −80 °C (−112 °F) 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 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.
Because DMSO increases the rate of absorption of some compounds through biological tissues, including skin, 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 (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.

A gel containing DMSO, dexpanthenol, and heparin, is sold in Germany and eastern Europe (commercialized under the Dolobene brand) for topical use in sprains, tendinitis, and local inflammation.[31]

In interventional radiology, DMSO is used as a solvent for ethylene vinyl alcohol in the Onyx liquid embolic agent, which is used in embolization, the therapeutic occlusion of blood vessels.

In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. Without it, up to 90% 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 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 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 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 drugs, including cisplatin, carboplatin, 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 for horses, 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.
Unlike dimethyl and diallyl disulfide (also with odors resembling garlic), the mono- and tri- sulfides (typically with foul odors), and other similar structures, the pure chemical DMSO is odorless.

Safety
Toxicity
DMSO is a non-toxic solvent with a median lethal dose higher than ethanol (DMSO: LD50, oral, rat, 14,500 mg/kg; ethanol: LD50, 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, it is listed as a Schedule 4 (S4) Drug, and a company has been prosecuted for adding it to products as a preservative.

Because DMSO easily penetrates the skin, substances dissolved in DMSO may be quickly absorbed. 
Glove selection is important when working with DMSO. Butyl rubber, fluoroelastomer, neoprene, or thick (15 mil / 0.4  mm) latex 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 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 was halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972.
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 0.3 mL/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 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) 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 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.[49

Receiving 
The main method for obtaining DMSO is the oxidation of dimethyl sulfide . 
In industry, this process is carried out using nitric acid . DMSO is a by-product of the pulp and paper industry . 
The annual production of DMSO is measured in tens of thousands of tons.

Under laboratory conditions, potassium periodate in an organic solvent – water system can be used for mild and selective oxidation of dimethyl sulfide . However, laboratory methods for the preparation of DMSO are of no practical importance. 
This is due to the inconvenience of working with dimethyl sulfide, as well as the low commercial cost of the finished solvent.

Physical and chemical properties 
When mixed with water, noticeable heating occurs. 
Reacts with methyl iodide to form a sulfoxonium ion that can react with sodium hydride.

Application 
Application as a solvent 
DMSO is an important bipolar aprotic solvent. It is less toxic than other members of this group, such as dimethylformamide , dimethylacetamide , N-methyl-2-pyrrolidone, HMPTA. Due to its strong dissolving power, DMSO is often used as a solvent in chemical reactions involving inorganic salts, in particular in nucleophilic substitution reactions. The acidic properties of DMSO are weak, so it has become an important solvent in the chemistry of carbanions . In DMSO, the values ​​of non-aqueous pKa were measured for hundreds of organic compounds .

Due to its high boiling point, DMSO evaporates extremely slowly under normal atmospheric pressure. 
This makes it a very convenient solvent for heating reactions. At the same time, a rather high melting point limits its use in the low temperature range. 
After the reaction is carried out in a DMSO solution, the reaction mixtures are most often diluted with water to precipitate organic substances.

The deuterated form of DMSO, also known as DMSO-d6, is a convenient solvent for NMR spectroscopy due to its high dissolving power for a wide range of substances, the simplicity of its own spectrum, and its stability at high temperatures. The disadvantages of DMSO-d6 as a solvent for NMR spectroscopy are its high viscosity, which broadens the signals in the spectrum, and its high boiling point, which makes it difficult to recover the substance after analysis. Often DMSO-d6 is mixed with CDCl 3 or CD 2 Cl 2 to lower the viscosity and melting point.

DMSO finds more and more applications in the production of microelectronics .

DMSO is more effective and safer than gasoline or dichloromethane for removing paint stains .

Along with nitromethane, DMSO is also a tool that removes “super-glue” (hardened, but still fresh) and uncured polyurethane foam . 
Apparently, DMSO reacts only with external super-glue molecules, thus forming a barrier against the penetration of DMSO into the depths (This is the only way to explain the extremely long removal of super-glue, which is effective only with prolonged friction of the super-glue surface with a cloth moistened with DMSO. deeper penetration with abundant wetting with DMSO is not observed). It is recommended to work with rubber gloves (upon contact with DMSO, the skin on the fingers wrinkles as from prolonged contact with water).

The properties of DMSO dissolution of deposits from engine oil (sludge, varnishes, carbon deposits) in the internals of internal combustion engines when introduced into the oil and directly into the combustion chamber are noteworthy, and the flushing efficiency is such that in some cases the release of stuck piston rings and cleaning of oil drainage holes in the pistons is achieved , however, paint and varnish coatings of engine parts may dissolve, followed by the ingress of coating flakes into the oil lines.

Application in biology 
DMSO is used in PCR to inhibit the pairing of parental DNA molecules. Before the start of the reaction, it is added to the PCR mixture and interacts with complementary DNA regions , preventing their pairing and reducing the number of side processes  .

DMSO is also used as a cryoprotectant . It is added to the cell environment to prevent cell damage during freezing . 
Approximately 10% DMSO can be used to safely cool cells and store them at liquid nitrogen temperature .

Application in medicine 
Main article: Dimexidum
It is used as a cryoprotectant in transplantology .

As a drug, purified dimethyl sulfoxide is used in the form of aqueous solutions (10-50%), as a local anti-inflammatory and analgesic agent, as well as in ointments – to increase the transdermal transfer of active substances, since it penetrates the skin and transfers other substances in a few seconds. The trade name of the drug is ” Dimexid “

Cleaning 
In addition to the impurity of water, dimethyl sulfoxide can also contain dimethyl sulphide and sulphones . These impurities are disposed of by keeping the DMSO for 12 hours over barium oxide , sodium hydroxide , drierite, or fresh activated alumina . After that, the substance is distilled under reduced pressure (~ 2-4 mm Hg, boiling point about 50 ° C ) over granules of sodium hydroxide or barium oxide. A 4A molecular sieve is used to store the purified DMSO .

Security 
DMSO penetrates easily through intact skin, therefore solutions of toxic substances in DMSO can lead to poisoning when in contact with the skin (transdermal). 
May irritate the skin, especially with undiluted DMSO .

Dimethyl sulfoxide (abbreviated as DMSO) is Dimethyl sulfoxide, unitary enterprise.  500g.a highly polar and water-miscible organic liquid. 
It is essentially odorless and low in toxicity. Like all dipolar aprotic solvents, DMSO has a relatively high boiling point. 
    When mixed with water, noticeable heating occurs. Reacts with methyl iodide to form a sulfoxonium ion that can react with sodium hydride.

Synonyms: methanesulfinylmethane, methyl sulfoxide, dimethyl (oxide) sulfur, DMSO, Dimethyl sulfoxide, DMSO.

 

 Dimethyl Sulfoxide Applications
    Dimethyl sulfoxide is an excellent solvent for the preparation of active pharmaceutical ingredients and intermediates. 
Many specific reactions are most effective in DMSO, resulting in higher yields. 
The high polarity of DMSO allows it to dissolve many compounds that other solvents cannot. 
DMSO itself is a reagent in the class of environmentally friendly oxidation reactions.
    The powerful soluble properties of DMSO allow high asset loading, resulting in highly concentrated formulations in agrochemical formulations. 
DMSO is a safe and effective liquid formulation solvent for a number of active ingredients used in herbicides, insecticides, and fungicidal formulations, including propiconazole, pinoxaden, pyroxasulfone, mentaconazole, imazafar, imazamethabenzmethyl, tribupyrimphos, cyfopriluthrin, glyphophiloflophenol.

Dimethyl sulfoxide as a cryopreservative

   DMSO has the unusual ability to drastically reduce the freezing point of water while maintaining the viability of many types of cells and tissues. 
It is added to the cell environment to prevent cell damage during freezing. 
Approximately 10% DMSO can be used to safely cool cells and store them at liquid nitrogen temperature. 
This led to its use in cryopreservation media for stem cells obtained from human umbilical cord blood and reproductive tissue.

Dimethyl sulfoxide as solvent

     For the production and processing of polymers, DMSO is used to produce carbon fiber and some high performance polymers. 
Since it can dissolve Dimethyl sulfoxide substance characteristicsmany polymers, DMSO can be used to cast polymer films and fibers useful in the manufacture of purification membranes. 
DMSO can be used to clean up polymer residues (polyurethane / polyester) from parts manufacturing.

 It is less toxic than other members of this group, such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPTA. 
Due to its strong dissolving power, DMSO is often used as a solvent in chemical reactions involving inorganic salts, in particular in nucleophilic substitution reactions. 
The acidic properties of DMSO are poorly expressed, so it has become an important solvent in the chemistry of carboanions. 
In DMSO, the values ​​of non-aqueous pKa were measured for hundreds of organic compounds

Due to its high boiling point, DMSO evaporates extremely slowly under normal atmospheric pressure. 
This makes it a very convenient solvent for heating reactions. 
At the same time, a rather high melting point limits its use in the low temperature range. 
After the reaction is carried out in a DMSO solution, the reaction mixtures are most often diluted with water to precipitate organic substances.

DMSO is more effective and safer than gasoline or dichloromethane for removing paint stains.

Along with nitromethane, DMSO is also a means of removing “super-glue” (hardened, but still fresh) and non-hardened polyurethane foam. 
Apparently, DMSO reacts only with external super-glue molecules, thus forming a barrier against the penetration of DMSO into the depths (This is the only way to explain the extremely long removal of the super-glue, which is effective only with prolonged friction of the super-glue surface with a cloth moistened with DMSO. deeper penetration with abundant wetting with DMSO is Cosmetic preparations with dimethyl sulfoxidenot observed).

 

Dimethyl sulfoxide in cosmetology.

It has unique dissolving properties, therefore it is now widely used in medicine and cosmetology. 
It easily and quickly (within a few seconds) penetrates through intact skin, transferring the active substances of medicinal or cosmetic products dissolved in it. 
Thus, it increases the effectiveness of ointments, creams, solutions – dramatically increasing the rate of penetration of active substances through the skin barrier. 
In addition, DMSO has anti-inflammatory and analgesic effects, and is harmful to many bacteria. 
DMSO in its pure form, when it gets on the skin, can cause irritation; therefore, for medicinal purposes, its aqueous solutions of various concentrations, usually from 10 to 70 percent, are most often used.

 

Dimethyl sulfoxide in crop production.

     The use of DMSO as a membrane penetrator creates a “sponge” effect. 
The plant absorbs nutrients through the leaf surface in the shortest possible time. 
DMSO is effective for the delivery of nutrients to the metabolic system of the plant and pulls substances in which it is dissolved through the membranes. 
Once in the cell, they are included in the physiological processes occurring in it, thereby increasing the activity of enzymes, activating the processes of respiration, the synthesis of proteins and carbohydrates, activating the processes of forming the area of ​​the leaf apparatus, increasing the productivity of photosynthesis. 
DMSO is a source of organic sulfur. The plant uses sulfur to constantly create new healthy cells and replace old ones with them. 
Without sulfur, the body will produce weak and dysfunctional cells. Sulfur maintains the permeability of cell membranes. 
DMSO ensures the entry of nutrients into the cell and the effective removal of toxins and waste products. 
DMSO is safe – it does not accumulate in the plant (no traces of DMSO were found in the plants after foliar dressing).
Dimexide is actively used in the fields as a part of fertilizers

Application phases

– in autumn 2 … 3 weeks before the onset of frost:

winter wheat, triticale, rye, winter barley – in the tillering phase;
winter rape – in the phase of 4 … 6 true leaves;
– in spring:

winter and spring wheat, triticale, rye, barley – in the tillering phase;
corn – in the phase of 5 … 7 leaves;
sunflower – in the phase of 6 … 8 leaves;
rapeseed – in the phase of 6 … 8 true leaves.
    Doses for foliar dressing are from 0.006 kg to 0.04 per 1 liter of solution. 
(concentration depends on water quality) Costs per hectare from 149 rubles Correct and timely use of the tank mixture guarantees an increase in frost and drought resistance of plants by 25% -30%. Retains a prolonged action for the entire growing season. 
The use of DMSO makes it possible to reduce the dosage and save the funds of the enterprise of plant protection products to 1/2 of the minimum recommended by the manufacturer of plant nutrients by 30%.

 

The use of dimethyl sulfoxide in the leather industryDimethyl sulfoxide in leather formulations

   In experiments with leather tissue, it was found that D MSO greatly enhances the transmission of water through it. 
For example, the rate of water penetration through the stratum corneum when using dimethyl sulfoxide in solution increases 125 times. 
It is obvious that dimexide overcomes the skin barrier through the follicles and intercellular spaces.
In addition to its great “transport capacity”, dimethyl sulfoxide can form complexes with metal ions with a variable valence, for example, chromium ions, and bind with collagen peptide groups. 
The described properties of dimethyl sulfoxide make it possible to use it in the process of dressing hides at the stage of processing the skin before the start of chrome tanning and directly in the tanning of the leather itself.
It was found during the study that the use of dimexide and its homologon during dressing leads to an improvement in the quality of leather, and a decrease in dressing time. and reducing the chromium oxide content in the spent tanning solution. 
Leathers, chrome tanned with the use of dimethyl sulfoxide (Dimexide), have better physical, mechanical and hygienic properties, and the content of chromium oxide in the leather increases ..

Application of dimethyl sulfoxide in biology

DMSO is used in polymerase chain reaction (PCR) to inhibit the pairing of parental DNA molecules. 
It is added to the PCR mixture before the start of the reaction, where it interacts with complementary DNA regions, preventing their pairing and reducing the number of side processes.

The use of dimethyl sulfoxide in medicine

As a drug, purified dimethyl sulfoxide is used in the form of aqueous solutions (10-50%), as a local anti-inflammatory and analgesic agent, as well as in ointments to increase the transdermal transfer of active substances, since it Dimethyl sulfoxide_chemistry.

Dimethyl sulfoxide

dimethyl sulphoxide
CAS names
Methane, 1,1′-sulfinylbis-

IUPAC names
Dimethyl sulphoxide, anhydrous
Dimethylsulfoxid
Dimethylsulfoxide
DMSO, Methyl Sulfoxide
methanesulfinylmethane
Methylsulfinidemethane
methylsulfinylmethan
methylsulfinylmethane

Dimethylsulfoxide
In Meyler’s Side Effects of Drugs (Sixteenth Edition), 2016
General information
Dimethylsulfoxide is an agent with a wide spectrum of pharmacological effects, including membrane penetration, anti-inflammatory effects, local analgesia, and weak bacteriostasis. 
The principal use of dimethylsulfoxide is as a vehicle for other drugs, thereby enhancing the effect of the drug, and aiding penetration of other drugs into the skin. Dimethylsulfoxide has been given orally, intravenously, or topically for a wide range of indications. It is also given by bladder instillation in the symptomatic relief of interstitial cystitis, and is used as a cryoprotectant for various human tissues.
In preparation for bone marrow transplantation, autologous hemopoietic stem cells are normally frozen in liquid nitrogen after harvesting. 
However, a cryoprotective agent is required, and dimethylsulfoxide is normally used. 
During and immediately after stem cell infusion, many adverse effects, which may be severe or life-threatening, have been reported. 
They include hypotension and hypertension, anaphylactic reactions, and cardiac and respiratory failure, all possibly due to dimethylsulfoxide, hemolysis induced by cryopreservation and thawing, and fluid overload.
In a retrospective study, 30 children were reviewed after bone marrow or peripheral autologous hemopoietic transplantation. 
At the time of infusion, hydrocortisone, chlorphenamine, and hyperhydration were administered to all patients, and furosemide and tropisetron to most. 
Vital signs and symptoms were monitored for 6 hours after the infusion. 
Thawing was performed rapidly at the bedside in a 42°C water-bath, and the cells were infused through a central venous catheter at 10 ml/minute. 
All 32 procedures were well tolerated; there were infusion-related adverse effects in 15 of 32 infusions, but none required specific therapy. 
There was mild bradycardia in nine patients, one reported abdominal pain, two reported headache, and three had hemoglobinuria. 
The authors concluded that a single-step cryopreservation technique aimed at limiting the total amount of dimethylsulfoxide is effective in avoiding most toxicity while not compromising post-thawing viability.
The efficacy and safety of dimethylsulfoxide are still relatively unclear; few studies have been performed in such a way as to permit reliable conclusions. 
Dimethylsulfoxide penetrates quickly through the tissues, and there are no great differences between its effects after different routes of administration. 
Adverse reactions are common, but can be avoided in large part by using more dilute solutions. 
Although the systemic toxicity of dimethylsulfoxide is considered to be low, it can potentiate the effect of simultaneously administered drugs. 
Combinations of dimethylsulfoxide with other toxic agents probably constitute its greatest toxic potential.

Dimethyl Sulfoxide (DMSO)
S.E. Gad, D.W. SullivanJr., in Encyclopedia of Toxicology (Third Edition), 2014
Toxicokinetics
DMSO is readily absorbed by animals and humans by dermal and oral routes and enhances absorption of many other chemicals by those routes. 
Higher concentrations of DMSO are more readily absorbed than more dilute solutions of DMSO in water. 
After dermal application, radiolabeled DMSO has been detected in blood within 5 min, along with halitosis resulting from a metabolite, dimethyl sulfide. 
Distribution to other organs has been reported to occur within 20 min. Radiolabeled DMSO was detected in bones and teeth of animals within 1 h. 
DMSO can affect ionic balance due to its facilitation of the absorption of many other substances through biological membranes. 
The major metabolites of DMSO in humans are dimethyl sulfone and dimethyl sulfide. 
Following oral administration, about two-thirds of the dose is excreted in urine as unchanged DMSO, ∼20% as dimethyl sulfone, and 5% is exhaled as dimethyl sulfide. 
These metabolites have also been identified in monkeys and rats. 
In the eyes, the highest levels appear to accumulate in the cornea, and the lowest in the lens. 
DMSO has a calculated half-life of 16 h in blood; the corresponding value for dimethyl sulfone is 38 h. 
About 3% of oral doses is exhaled as dimethyl sulfide in humans; the percentage appears to be slightly higher in animals. 
DMSO can persist in serum for more than 2 weeks after a single exposure.

Abstract
Abstract Image
Dimethylsulfoxide (DMSO) is an aprotic solvent that has the ability to induce cell fusion and cell differentiation and enhance the permeability of lipid membranes. 
It is also an effective cryoprotectant. 
Insights into how this molecule modulates membrane structure and function would be invaluable toward regulating the above processes and for developing chemical means for enhancing or hindering the absorption of biologically active molecules, in particular into or via the skin. 
We show here by means of molecular simulations that DMSO can induce water pores in dipalmitoyl-phosphatidylcholine bilayers and propose this to be a possible pathway for the enhancement of penetration of actives through lipid membranes. 
DMSO also causes the membrane to become floppier, which would enhance permeability, facilitate membrane fusion, and enable the cell membrane to accommodate osmotic and mechanical stresses during cryopreservation.

Roles Classification 

Chemical Role(s):    polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.

radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.

Biological Role(s):    Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.

non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.

alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. 
It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. 
It could also be used as a component of poison gases.

Application(s):    polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.

non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.

antidote
Any protective agent counteracting or neutralizing the action of poisons.
MRI contrast agent

dimethyl sulfoxide has role Escherichia coli metabolite 
dimethyl sulfoxide has role alkylating agent 
dimethyl sulfoxide has role antidote 
dimethyl sulfoxide has role MRI contrast agent 
dimethyl sulfoxide has role non-narcotic analgesic 
dimethyl sulfoxide has role polar aprotic solvent 
dimethyl sulfoxide has role radical scavenger 
dimethyl sulfoxide is a sulfoxide 
dimethyl sulfoxide is a volatile organic compound

Dimethyl Sulfoxide (DMSO)
Dimethyl Sulfoxide (DMSO) is a colorless solvent with the formula (CH3)2SO. DMSO is a PCR additive that functions in helping denature template and primer DNA, such as when the GC content is high. It may also aid in relaxing supercoiled plasmids for amplification. If added, the working concentration in a typical PCR reaction can range from 3 to 10 percent. DMSO is also used as a cryoprotectant, protecting cells during the freezing process by reducing ice formation.

The story of dimethyl sulfoxide (DMSO) is an unusual one. This by-product of the paper making process was discovered in Germany in the late 19th century. It’s a colorless liquid that gained notoriety for its ability to penetrate skin and other biological membranes.

Scientists discovered that they could use DMSO as a transportation device to pass small molecules through skin. Since then, scientists have researched the potential benefits and risks of using DMSO to treat a variety of conditions

Benefits
Some doctors began to use DMSO to treat cases of skin inflammation and diseases such as scleroderma because of its ability to penetrate skin. Scleroderma is a rare disorder that causes your skin to harden.

Some studies have found that DMSO may also be useful for treating certain side effects of chemotherapy, reports the Memorial Sloan Kettering Cancer Center (MSKCC). Specifically, DMSO may help treat chemotherapy extravasations.

This condition occurs when the drugs used to treat cancer leak and become trapped in surrounding tissues. It can cause symptoms that include:

tingling
burning
pain
swelling
redness at your chemotherapy injection site.
If left untreated, it can lead to blistering, ulcers, and tissue death.

Research
Preliminary research evidence reported in PLOS ONETrusted Source also suggests that DMSO might be effective for treating Alzheimer’s disease, a condition with no known cure.

According to MSKCC, some researchers suggests that DMSO might also be useful for:

reducing pain and inflammation caused by arthritis
treating bladder pain and inflammation
slowing the progression of cancer
However, more research is needed to assess the potential benefits and risks of using DMSO to treat these conditions. To date, the Food and Drug Administration (FDA) has officially approved the use of DMSO in humans for only one purpose: to treat interstitial cystitis.

This is a chronic condition that causes inflammation in your bladder. To treat it, your doctor may flush DMSO into your bladder using a catheter over several of weeks. It’s also available in pill form and as a topical lotion, but these formulations are not approved for use by the FDA.

Risks
While DMSO has been approved for a variety of uses in dogs and horses, interstitial cystitis remains its only FDA-approved use in humans. This reflects concerns over potential toxicities, reports MSKCC.

The use of DMSO in animals has been linked to changes to their eye lenses. This has raised concerns about the potential of DMSO to damage human eyes. More research is needed to assess these risks.

Other reported side effects from DMSO tend to be minor. The most commonly reported side effect is a strong garlic flavor in your mouth for several hours after you have been treated with it. Your skin may also give off a garlic-like odor for up to 72 hours after being treated.

Doctors agree that you should be cautious when it comes to applying DMSO topically. It may cause dry, scaly, and itchy skin. It may also interact with other medications. Unhealthy substances may also be absorbed through your skin along with the DMSO. And it may also cause urine discoloration and agitation.

The Takeaway
DMSO has only been approved by the FDA in the United States to treat interstitial cystitis. 
But we probably haven’t heard the last of it. DMSO may have promise in treating a variety of other conditions that include:

arthritis
cancer
chemotherapy
extravasations
Alzheimer’s disease
However, research to date has been inconsistent. More research on its potential uses will likely continue for years to come.

Talk to your doctor before using any products that contain DMSO. They can help you understand the potential benefits and risks.

Dimethylsulfoxide
In Meyler’s Side Effects of Drugs (Sixteenth Edition), 2016
General information
Dimethylsulfoxide is an agent with a wide spectrum of pharmacological effects, including membrane penetration, anti-inflammatory effects, local analgesia, and weak bacteriostasis. 
The principal use of dimethylsulfoxide is as a vehicle for other drugs, thereby enhancing the effect of the drug, and aiding penetration of other drugs into the skin. 
Dimethylsulfoxide has been given orally, intravenously, or topically for a wide range of indications. 
It is also given by bladder instillation in the symptomatic relief of interstitial cystitis, and is used as a cryoprotectant for various human tissues.
In preparation for bone marrow transplantation, autologous hemopoietic stem cells are normally frozen in liquid nitrogen after harvesting. 
However, a cryoprotective agent is required, and dimethylsulfoxide is normally used. 
During and immediately after stem cell infusion, many adverse effects, which may be severe or life-threatening, have been reported. 
They include hypotension and hypertension, anaphylactic reactions, and cardiac and respiratory failure, all possibly due to dimethylsulfoxide, hemolysis induced by cryopreservation and thawing, and fluid overload.
In a retrospective study, 30 children were reviewed after bone marrow or peripheral autologous hemopoietic transplantation. 
At the time of infusion, hydrocortisone, chlorphenamine, and hyperhydration were administered to all patients, and furosemide and tropisetron to most. 
Vital signs and symptoms were monitored for 6 hours after the infusion. 
Thawing was performed rapidly at the bedside in a 42°C water-bath, and the cells were infused through a central venous catheter at 10 ml/minute. 
All 32 procedures were well tolerated; there were infusion-related adverse effects in 15 of 32 infusions, but none required specific therapy. 
There was mild bradycardia in nine patients, one reported abdominal pain, two reported headache, and three had hemoglobinuria. 
The authors concluded that a single-step cryopreservation technique aimed at limiting the total amount of dimethylsulfoxide is effective in avoiding most toxicity while not compromising post-thawing viability.
The efficacy and safety of dimethylsulfoxide are still relatively unclear; few studies have been performed in such a way as to permit reliable conclusions. 
Dimethylsulfoxide penetrates quickly through the tissues, and there are no great differences between its effects after different routes of administration. 
Adverse reactions are common, but can be avoided in large part by using more dilute solutions. 
Although the systemic toxicity of dimethylsulfoxide is considered to be low, it can potentiate the effect of simultaneously administered drugs. 
Combinations of dimethylsulfoxide with other toxic agents probably constitute its greatest toxic potential

Pharmacotherapy of joint and tendon disease
Carl A. Kirker-Head, Hillary Feldmann, in Equine Sports Medicine and Surgery (Second Edition), 2014
Mechanism of action
Dimethyl sulfoxide (DMSO), a by-product of the lumber industry, was originally used as an industrial solvent. 
DMSO was first employed as a therapeutic agent in the treatment of interstitial cystitis and arthritis during the early 1960s. 
Since that time, DMSO has been widely used within the equine industry alone or mixed with corticosteroids to reduce soft tissue swelling, inflammation, and edema secondary to acute trauma.291–292
The pharmacological effects of DMSO and its metabolite, dimethyl sulfide, are diverse. 
DMSO has been shown to possess superoxide dismutase activity. 
As a result, DMSO can inactivate superoxide radicals; inhibit hydroxyl radical mediated depolymerization of hyaluronan; and suppress PG synthesis by oxygen-derived free radicals.
DMSO is believed to possess analgesic properties secondary to the inhibition of prostaglandins E2, F2α, H2, and G2. 
The analgesic effect of DMSO has been compared to that produced by narcotic analgesics and been found to be efficacious for both acute and chronic musculoskeletal pain.296
In addition to its anti-inflammatory effects, DMSO possesses the ability to rapidly and easily penetrate the skin. 
DMSO serves as a carrier to enhance the penetration of various agents through the skin into underlying synovial, connective, and interstitial tissues.
 DMSO has been shown to enhance the penetration of percutaneous steroids three-fold, and the ability of cortisone to locally stabilize lysosomes by 100-fold.
In addition, DMSO increases the local anti-arthritic effect of hydrocortisone 10-fold when used as a carrier.
DMSO has an anti-arthritic effect independent of its ability to promote corticosteroid absorption.
Topical application of the gel formulation of DMSO decreased the mean synovial white blood cell concentrations in an equine synovitis model.
 DMSO has been shown to help resolve tissue inflammation through increased blood flow and promote vascular dilation.
DMSO causes collagen dissolution, which may help to restore pliability to fibrosed tissues.
Topical application of DMSO solution, in rabbits, reduced ankle stiffness in a fracture model of arthritis.300 Both the anti-inflammatory and anti-arthritic effects of DMSO appear to be more effective when used to treat acute versus chronic inflammatory conditions.
Both DMSO and dimethyl sulfide are extensively and rapidly distributed to all areas of the body after oral, intravenous, and topical administration.
The half-life of the parent compound and its metabolite is nine hours.
DMSO is primary excreted through the kidney, but secondary elimination through the respiratory tract and bile does occur.

Hematopoietic Stem Cell Collections and Cellular Therapies
Ljiljana V. Vasovic MD, … Ruchika Goel MD, MPH, in Clinical Principles of Transfusion Medicine, 2018
DMSO Toxicity
DMSO is a rapidly penetrating molecule that increases cells tolerance to osmotic stress induced by cryopreservation. 
DMSO was originally used as an antiinflammatory reagent but was later found to cause an array of side effects when administered to patients.
DMSO toxicity in HPC product infusions was shown to affect multiple organs, including respiratory, cardiovascular, gastrointestinal, hepatic, and renal systems.
DMSO is also associated with intravascular hemolysis.
Side effects related to infusion of thawed products are usually mild to moderate, most commonly nausea, vomiting, hypertension, or allergic reactions.
Severe side effects are rare but cardiovascular, neurologic, and respiratory side effects have been reported, with some of them being severe or fatal.
The rate of side effects was shown to correlate with higher DMSO volume.
Current recommendation is to infuse less than 1 mL DMSO/kg recipient weight.

Pharmacologic Management of Complex Regional Pain Syndrome
Rena Beckerly MD, MBA, Honorio T. Benzon MD, in Essentials of Pain Medicine (Fourth Edition), 2018
Pharmacology
DMSO is an organosulfur compound that readily passes through membranes depending on the strength of the preparation. 
DMSO 70%–90% will readily pass through the skin. 
This permeability allows the drug to enhance the diffusion of other medications across membranes (e.g., morphine sulfate, penicillin, steroids, and insulin). 
Relief is reported almost immediately and lasts up to 6 hours. This has made DMSO ideal for acute pain in athletes who require immediate pain relief. 
The agent is quickly eliminated from the body. 
Chronic pain patients may need to apply DMSO for nearly 6 weeks prior to noticing an effect.

Collection and processing of marrow and blood hematopoietic stem cells
Michele Cottler-Fox, … John Theus, in Hematopoietic Stem Cell Transplantation in Clinical Practice, 2009
Addition of cryoprotectant
Dimethylsulfoxide (DMSO) is the cryoprotective agent most widely used to cryopreserve hematopoietic stem cells at present. 
DMSO is a universal solvent capable of stabilizing cell membranes under rapidly changing conditions, preventing intracellular ice crystal formation during freezing and heat release during the period of phase transition. 
DMSO has been described as toxic to stem cells at room temperature, for which reason investigators have emphasized the need to add it at 4°C to cells prior to controlled-rate freezing and to begin cryopreservation quickly thereafter. 
A final concentration of 10% DMSO with albumin or human serum is commonly used, with some centers using hydroxyethyl starch to help stabilize cell membranes and reduce the amount of DMSO used to 5%.
A new cryopreservative, Cryostor (BioLife Solutions Inc., Corning, NY), is also available. 
This compound modulates cellular biochemistry during the freezing process and is free of serum, proteins, and DMSO.

Abstract
Dimethylsulfoxide (DMSO) is an aprotic solvent that has the ability to induce cell fusion and cell differentiation and enhance the permeability of lipid membranes. 
It is also an effective cryoprotectant. 
Insights into how this molecule modulates membrane structure and function would be invaluable toward regulating the above processes and for developing chemical means for enhancing or hindering the absorption of biologically active molecules, in particular into or via the skin. 
We show here by means of molecular simulations that DMSO can induce water pores in dipalmitoyl-phosphatidylcholine bilayers and propose this to be a possible pathway for the enhancement of penetration of actives through lipid membranes. 
DMSO also causes the membrane to become floppier, which would enhance permeability, facilitate membrane fusion, and enable the cell membrane to accommodate osmotic and mechanical stresses during cryopreservation

Growth of agrochemicals sector, as well as demand for environment-friendly and nontoxic solvents is expected to boost the global DMSO market during the forecast period. Even though it’s used as a drug, the FDA (Food and Drug Administration) has limited its use for treating and managing bladder injury only. However, the FDA has recently started trials for use of DMSO for closed head injuries, and it’s expected that increasing pharmaceutical applications will augur well for growth of the DMSO market during the forecast period.

DiMethyl Sulfoxide (DMSO) Market Segmentation
The global dimethyl sulfoxide market is segmented on the basis of raw materials, applications, and region.

On the basis of raw materials, the global DiMethyl Sulfoxide market is segmented into:

Black Liquor
Sulphur
Raw Cotton
Lignin
Based on the applications, the global DiMethyl Sulfoxide market is segmented into:

Pharmaceuticals
Agrochemicals
Electronics
Fine Chemicals
Coatings
Cleaning applications

Dimethyl sulfoxide (DMSO) is a highly polar and water miscible organic liquid. Due to its powerful solvent, it is named as “Universal solvent”.

Dimethyl sulfoxide has many properties, such as powerful solvent, high flash point and boiling point, excellent toxicological and eco toxicological profile, recyclable, biodegradable and low odor, so it is wildly used in pharmaceutical, electronic and chemical fields.