'''Dimethyl sulfoxide''' (DMSO) is the [[chemical compound]] with the [[chemical formula|formula]] (CH<sub>3</sub>)<sub>2</sub>SO. This colorless liquid is an important [[polar solvent|polar]] [[aprotic solvent]] that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, allowing the handler to taste it. Its taste has been described as [[oyster]]- or [[garlic]]-like.
There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
<!--Non–Guideline-Supported Use (Adult)-->
|offLabelAdultNoGuideSupport======Condition1=====
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
<!--Pediatric Indications and Dosage-->
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed======Condition1=====
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>FDA-Labeled Use</i> of {{PAGENAME}} in pediatric patients.
<!--Off-Label Use and Dosage (Pediatric)-->
<!--Guideline-Supported Use (Pediatric)-->
|offLabelPedGuideSupport======Condition1=====
* Developed by:
* Class of Recommendation:
* Strength of Evidence:
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
<!--Non–Guideline-Supported Use (Pediatric)-->
|offLabelPedNoGuideSupport======Condition1=====
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
<!--Contraindications-->
|contraindications=* Condition1
<!--Warnings-->
|warnings=* Description
====Precautions====
* Description
<!--Adverse Reactions-->
<!--Clinical Trials Experience-->
|clinicalTrials=There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
=====Body as a Whole=====
=====Cardiovascular=====
=====Digestive=====
=====Endocrine=====
=====Hematologic and Lymphatic=====
=====Metabolic and Nutritional=====
=====Musculoskeletal=====
=====Neurologic=====
=====Respiratory=====
=====Skin and Hypersensitivy Reactions=====
=====Special Senses=====
=====Urogenital=====
=====Miscellaneous=====
<!--Postmarketing Experience-->
|postmarketing=There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
=====Body as a Whole=====
=====Cardiovascular=====
=====Digestive=====
=====Endocrine=====
=====Hematologic and Lymphatic=====
=====Metabolic and Nutritional=====
=====Musculoskeletal=====
=====Neurologic=====
=====Respiratory=====
=====Skin and Hypersensitivy Reactions=====
=====Special Senses=====
=====Urogenital=====
=====Miscellaneous=====
<!--Drug Interactions-->
|drugInteractions=* Drug
:* Description
<!--Use in Specific Populations-->
|FDAPregCat=
|useInPregnancyFDA=* '''Pregnancy Category'''
|useInPregnancyAUS=* '''Australian Drug Evaluation Committee (ADEC) Pregnancy Category'''
There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of {{PAGENAME}} in women who are pregnant.
|useInLaborDelivery=There is no FDA guidance on use of {{PAGENAME}} during labor and delivery.
|useInNursing=There is no FDA guidance on the use of {{PAGENAME}} with respect to nursing mothers.
|useInPed=There is no FDA guidance on the use of {{PAGENAME}} with respect to pediatric patients.
|useInGeri=There is no FDA guidance on the use of {{PAGENAME}} with respect to geriatric patients.
|useInGender=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific gender populations.
|useInRace=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific racial populations.
|useInRenalImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with renal impairment.
|useInHepaticImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with hepatic impairment.
|useInReproPotential=There is no FDA guidance on the use of {{PAGENAME}} in women of reproductive potentials and males.
|useInImmunocomp=There is no FDA guidance one the use of {{PAGENAME}} in patients who are immunocompromised.
<!--Administration and Monitoring-->
|administration=* Oral
* Intravenous
|monitoring=There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.
* Description
<!--IV Compatibility-->
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.
<!--Overdosage-->
|overdose====Acute Overdose===
====Signs and Symptoms====
* Description
====Management====
==Production==
* Description
Dimethyl sulfoxide is a by-product of [[wood pulp]]ing. One of the leading suppliers of DMSO is the [[Gaylord Chemical Corporation]] in the [[USA]].
==Applications==
===Chronic Overdose===
===Solvent===
DMSO is an important [[polar aprotic solvent]]. It is less toxic than other members of this class such as [[dimethylformamide]], [[dimethylacetamide]], [[Methylpyrrolidone|''N''-methyl-2-pyrrolidone]], [[Hexamethylphosphoramide|HMPA]]. Because of its excellent solvating power, DMSO is frequently used as [[solvent]] for chemical reactions involving salts. Its polarity accelerates reactions with charged transition states, such as [[SN2|S<sub>N</sub>2]] alkylations of indoles and [[phenols]]. Because DMSO is only weakly acidic, it tolerates relatively strong bases. A practical problem with DMSO as a solvent is its high boiling point, thus its solutions are not typically evaporated. Instead, reactions conducted in DMSO are often diluted with water to isolate organic products. DMSO is an effective [[paint stripper]], being safer than many of the others such as [[nitromethane]] and [[dichloromethane]].
In its [[deuterium|deuterated]] form, i.e. [[Deuterated DMSO|DMSO-d<sub>6</sub>]], it is a useful but expensive solvent for [[Nuclear magnetic resonance|NMR]] spectroscopy, again due to its ability to dissolve a wide range of analytes and its own simple spectrum. Disadvantages to the use of DMSO-d<sub>6</sub> are its high viscosity, which broadens signals, and high boiling point, which interferes with sample recovery from the NMR solvent. Often it is used with [[deuterated chloroform|deuterochloroform]], because the 1:1 mixture has a low viscosity.
There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
===Reactions===
<!--Pharmacology-->
The sulfur center in DMSO is nucleophilic toward soft electrophiles and the oxygen is nucleophilic toward hard electrophiles. The methyl groups of DMSO are somewhat acidic in character (p''K''<sub>a</sub>=35) due to the stabilization of the resultant [[carbanion]] by the S(O)R group.
DMSO reacts with [[methyl iodide]] to form a sulfoxonium salt [(CH<sub>3</sub>)<sub>3</sub>SO]I, which can be deprotonated with [[sodium]] [[hydride]] to form the [[sulfur]] [[ylide]]:
:[(CH<sub>3</sub>)<sub>3</sub>SO]I + NaH → [(CH<sub>3</sub>)<sub>2</sub>CH<sub>2</sub>SO + NaI + H<sub>2</sub>
|mechAction=*
In [[organic synthesis]], DMSO is used as an oxidant,<ref>{{cite journal|author= Epstein W.W., Sweat F.W.|title=Dimethyl Sulfoxide Oxidations|journal= [[Chemical Reviews]]|year= 1967| volume= 67|pages= 247-260|doi=10.1021/cr60247a001}}</ref> such as the [[Pfitzner-Moffatt oxidation]] and the [[Swern oxidation]].<ref>{{cite journal | author= Tidwell, T.T. | title=Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update | journal= Synthesis | year= 1990 | volume = 1990 | pages=857-870 | doi=10.1055/s-1990-27036}}</ref>
<!--Structure-->
|structure=*
Products of [[ozonolysis]], [[trioxolane]]s, are quenched with [[dimethyl sulfide]] to produce [[aldehyde]]s and DMSO.
: [[File:{{PAGENAME}}01.png|thumb|none|600px|This image is provided by the National Library of Medicine.]]
===Biology===
<!--Pharmacodynamics-->
DMSO is used in the [[PCR reaction]] to inhibit [[Polymerase chain reaction#Hairpins|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, allowing otherwise troublesome reactions to occur. However, use of DMSO in PCR increases the [[mutation]] rate.
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.
DMSO also sees use as a [[cryoprotectant]], added to cell media in order to prevent the cells dying as they are frozen. Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at -20°C or stored in [[liquid nitrogen]] safely.
<!--Pharmacokinetics-->
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.
===Medicine===
<!--Nonclinical Toxicology-->
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 percent of frozen cells will become inactive. It is particularly important in the freezing and long-term storage of [[embryonic stem cells]] and [[hematopoietic stem cell]]s, which are often frozen in a mixture of 10% DMSO and 90% fetal calf [[blood plasma|serum]]. As part of an autologous [[bone marrow transplant]] the DMSO is re-infused along with the patient's own [[hematopoietic stem cell]]s.
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.
Use of DMSO in medicine dates from around [[1963]], when a [[University of Oregon]] Medical School team, headed by [[Stanley Jacob]], discovered it could penetrate the skin and other membranes without damaging them and could carry other compounds into a biological system.
<!--Clinical Studies-->
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.
In a 1978 study at the [[Cleveland Clinic]] Foundation in [[Cleveland, Ohio]], researchers concluded that DMSO brought significant relief to the majority of the 213 patients with inflammatory [[genitourinary]] disorders that were studied. They recommended [[DMSO]] for all inflammatory conditions not caused by infection or tumor in which symptoms were severe or patients failed to respond to conventional therapy.
<!--How Supplied-->
|howSupplied=*
|storage=
|packLabel=
<!--Patient Counseling Information-->
|fdaPatientInfo=There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.
Some people report an onion- or garlic-like taste after touching DMSO. ([[Onion]] and [[garlic]] also derive their stinginess from sulfoxides [[syn-propanethial-S-oxide]] and [[allicin]].) In the medical field DMSO is predominantly used as a topical [[analgesic]], a vehicle for topical application of pharmaceuticals, as an [[anti-inflammatory]] and an [[antioxidant]]. It has been examined for the treatment of numerous conditions and ailments. The [[Food and Drug Administration]] (FDA) has approved DMSO usage only for the [[palliative]] treatment of [[interstitial cystitis]]. Also, DMSO is commonly used in the veterinary field as a [[liniment]] for horses.
<!--Precautions with Alcohol-->
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
Because DMSO increases the rate of absorption of some compounds through organic [[Biological tissue|tissues]] including [[skin]], it can be used as a drug delivery system.
<!--Brand Names-->
|brandNames=* ®<ref>{{Cite web | title = | url = }}</ref>
Dimethyl sulfoxide dissolves a variety of organic substances, including [[carbohydrate]]s, [[polymer]]s, [[peptide]]s, as well as many inorganic salts and gases. Loading levels of 50-60 wt.% are often observed vs 10-20 wt.% with typical solvents. For this reason DMSO plays a role in sample management and [[High-throughput screening]] operations in drug design.<ref>{{cite journal | author=Balakin, K. V., Savchuk, N. P., Tetko I. V. | journal=Current Medicinal Chemistry | year=2006 | volume= 13 | issue=2 | pages 223-41 | title=In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions) | doi=10.2174/092986706775197917}}</ref>
<!--Look-Alike Drug Names-->
|lookAlike=* A® — B®<ref name="www.ismp.org">{{Cite web | last = | first = | title = http://www.ismp.org | url = http://www.ismp.org | publisher = | date = }}</ref>
====History in Medicine====
<!--Drug Shortage Status-->
On September 9, 1965, the ''Wall Street Journal'' reported the death of an Irish woman after undergoing DMSO treatment for a sprained wrist <ref> Carley W. DMSO May Have Caused Death of Woman, Makers of 'Wonder' Drug Warn Doctors. Wall Street Journal. September 9, 1965:6.</ref> Clinical research using DMSO halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972. In 1978, the FDA approved DMSO for treating interstitial cystis. In 1980, Congress held hearings on claims that the FDA was slow in approving DMSO for other medical uses. In 2007, the FDA granted "fast track" designation on clinical studies of DMSO's use in reducing brain tissue swelling following traumatic brain injury.
|drugShortage=
}}
{{PillImage
|fileName=No image.jpg
}}
{{LabelImage
|fileName={{PAGENAME}}11.png
}}
{{LabelImage
|fileName={{PAGENAME}}11.png
}}
<!--Pill Image-->
==Safety==
MSDS recommends wearing safety glasses because DMSO can cause chronic damage to the eyes.<ref>{{cite web | publisher = [[Oxford University]] | title = Safety data for methyl sulfoxide | url = http://ptcl.chem.ox.ac.uk/MSDS/ME/methyl_sulfoxide.html}}</ref> Glove selection is also important when working with DMSO. Thick rubber gloves are recommended, and nitrile gloves, which are very commonly used in chemical laboratories, have been found to dissolve rapidly with exposure to DMSO.<ref>{{cite web | publisher = [[Cornell University]] | title = Chemical Hygiene Plan | url = http://www.ehs.cornell.edu/geneva/chp/11.glove.selec.htm | date = September 99}}</ref> Because DMSO easily penetrates the skin, substances dissolved in DMSO may be quickly absorbed. For instance, a solution of [[sodium cyanide]] in DMSO can cause [[cyanide]] poisoning through skin contact. DMSO by itself has low toxicity.<ref>Vignes, Robert (August 2000). [http://www.gaylordchemical.com/bulletins/Vignes-ACS.pdf Dimethyl Sulfoxide (DMSO): A "new" clean, unique, superior solvent], American Chemical Society Annual Meeting</ref> Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides; at a low temperature, this reaction produces the oxidant for [[Swern oxidation]].
Recently, it was found that DMSO waste disposal into [[sewers]] can cause environmental odor problems in cities: Waste water bacteria transform DMSO under [[hypoxic]] (anoxic) conditions into [[dimethyl sulfide]] (DMS) that is slightly toxic and has a strong disagreeable odor, similar to rotten cabbage.<ref>{{cite journal
|author= Glindemann, D., Novak, J., Witherspoon, J.
|title= Dimethyl Sulfoxide (DMSO) Waste Residues and Municipal Waste Water Odor by Dimethyl Sulfide (DMS): the North-East WPCP Plant of Philadelphia.
|journal= Environmental Science and Technology
|year= 2006
| volume = 40
| issue = 1
|pages=202-207
|doi=10.1021/es051312a S0013-936X(05)01312-X }}
</ref>
==See also==
<!--Label Display Image-->
*[[Methylsulfonylmethane]] (MSM), a related chemical often used as a dietary supplement
* [[Dimethyl sulfate]] (DMS), a [[mutagenic]] [[alkylation|alkylating]] compound
WikiDoc MAKES NO GUARANTEE OF VALIDITY. WikiDoc is not a professional health care provider, nor is it a suitable replacement for a licensed healthcare provider. WikiDoc is intended to be an educational tool, not a tool for any form of healthcare delivery. The educational content on WikiDoc drug pages is based upon the FDA package insert, National Library of Medicine content and practice guidelines / consensus statements. WikiDoc does not promote the administration of any medication or device that is not consistent with its labeling. Please read our full disclaimer here.
Black Box Warning
ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
Content
Overview
Dimethyl sulfoxide is a that is FDA approved for the of . There is a Black Box Warning for this drug as shown here. Common adverse reactions include .
Adult Indications and Dosage
FDA-Labeled Indications and Dosage (Adult)
Condition1
Dosing Information
Dosage
Condition2
Dosing Information
Dosage
Condition3
Dosing Information
Dosage
Condition4
Dosing Information
Dosage
Off-Label Use and Dosage (Adult)
Guideline-Supported Use
Condition1
Developed by:
Class of Recommendation:
Strength of Evidence:
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Guideline-Supported Use of Dimethyl sulfoxide in adult patients.
Non–Guideline-Supported Use
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Non–Guideline-Supported Use of Dimethyl sulfoxide in adult patients.
Pediatric Indications and Dosage
FDA-Labeled Indications and Dosage (Pediatric)
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding FDA-Labeled Use of Dimethyl sulfoxide in pediatric patients.
Off-Label Use and Dosage (Pediatric)
Guideline-Supported Use
Condition1
Developed by:
Class of Recommendation:
Strength of Evidence:
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Guideline-Supported Use of Dimethyl sulfoxide in pediatric patients.
Non–Guideline-Supported Use
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Non–Guideline-Supported Use of Dimethyl sulfoxide in pediatric patients.
Contraindications
Condition1
Warnings
ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
Content
Description
Precautions
Description
Adverse Reactions
Clinical Trials Experience
There is limited information regarding Clinical Trial Experience of Dimethyl sulfoxide in the drug label.
Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous
Postmarketing Experience
There is limited information regarding Postmarketing Experience of Dimethyl sulfoxide in the drug label.
