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Methyl sulfoxide(CAS No. 67-68-5)

Methyl sulfoxide C2H6OS (cas 67-68-5) Molecular Structure

67-68-5 Structure

Identification and Related Records

Methyl sulfoxide
【CAS Registry number】
Dimethyl sulfoxide, USP Grade DMSO, USP Grade
DMSO~Methyl sulphoxide
methyl sulfoxide B&J brand 1 L
methyl sulfoxide absolute over molecular sieve (H2O <0.01%)
dimethyl sulfoxide hybri-max sterile*filtered
dimethyl sulfoxide plant cell culture*tested
Dimethyl sulfoxide, sterile filtered DMSO, sterile filtered
Diemthyl Sulfoxide
Dimethyl Sulfoxide BP
Dimethyl sulphoxide
DMSO/NMP (Dimethylsulfoxide/1-Methyl-2-pyrrolidone)
Dimethyl sulfoxide
Dimethylsulfoxide Sulfinylbis
【Molecular Formula】
C2H6OS (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

colorless liquid
【Melting Point】
【Boiling Point】
【Refractive Index】
【Flash Point】
clear colorless
Stable. Incompatible with a very wide range of materials, including acid chlorides, strong acids, strong oxidizing agents, strong reducing agents, phosphorus halides, moisture, copper wool + trichloroacetic acid. Reacts violently with a number of materials - consult a full data sheet before use. Hygroscopic.
【HS Code】
【Storage temp】
Store at RT.
【Spectral properties】
Index of refraction: 1.4795 at 20 deg C/D; 1.4787 at 21 deg C/D
Index refraction: 1.4770 at 20 deg C/D
IR: 4358 (Coblentz Society Spectral Collection)
UV: 6-5 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 535 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 158 (Stothers Carbon13 NMR Spectroscopy Academic Press, NY)
MASS: 19238 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
Raman 28: (Dollish Characteristic Raman Frequencies of Organic Compounds John Wiley and Sons, New York)
Intense mass spectral peaks: 45 m/z, 63 m/z, 78 m/z
【Computed Properties】
Molecular Weight:78.13344 [g/mol]
Molecular Formula:C2H6OS
H-Bond Donor:0
H-Bond Acceptor:2
Rotatable Bond Count:0
Exact Mass:78.013936
MonoIsotopic Mass:78.013936
Topological Polar Surface Area:36.3
Heavy Atom Count:4
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Hazard Codes of Dimethyl sulfoxide (CAS NO.67-68-5):?Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-37/39-26-36-23
S24/25:Avoid contact with skin and eyes.?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S23:Do not breathe vapour.
WGK Germany: 1
RTECS: PV6210000
F: 3
HS Code: 29309070

【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
... Based on chemical and physical properties alone, /dimethyl sulfoxide/ is ranked 10th/ of the ten most potentially irritating solvents /From table/.
【Fire Fighting Procedures】
To fight fire use water, foam, carbon dioxide, or dry chemical.
【Fire Potential】
Combustible when exposed to heat flame or oxidizing materials.
Dimethyl sulfoxide is presently available as Rimso-5, in a 50% aqueous solution.
U.S. - 50% [Rimso-50; GENERIC]; Canada - 50% [Rimso-50].
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl dimethyl sulfoxide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Dimethyl sulfoxide solution. (a) Specifications. Dimethyl sulfoxide contains 90 percent of dimethyl sulfoxide and 10% of water ... (c) Conditions of use. (1) It is used or intended for use as a topical application to reduce acute swelling due to trauma ... (2) Not for use in horses and dogs intended for breeding purposes nor in horses slaughtered for food. Other topical medications should only be used when the dimethyl sulfoxide treated area is thoroughly dry. Do not administer by any other route (3) For use by or on the order of a licensed veterinarian.
Dimethyl sulfoxide get. (a) Specifications. Dimethyl sulfoxide gel, veterinary contains 90 percent dimethyl sulfoxide in an aqueous gel ... (c) Conditions of use-(1) Indications for use. For use on horses and dogs as a topical application to reduce acute swelling due to trauma. ... (3) Limitations. Do not use in horses and dogs intended for breeding purposes or in horses slaughtered for food. Restricted to topical use on horses and dogs only. Due to rapid penetrating ability of dimethyl sulfoxide, rubber gloves should be worn when applying the drug. No other medications should be present on the skin prior to application of the drug. Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Fluocinolone acetonide, dimethyl sulfoxide solution. Fluocinolone acetonide, dimethyl sulfoxide solution. (a) Specifications. Each milliliter of solution contains 0.01 percent fluocinolone acetonide and 20 percent dimethyl sulfoxide with propylene glycol and citric acid. ... (c) Conditions of use. (1) The drug is used in dogs for the relief of impaction commonly present in apparently normal anal sacs, for the reversal of inflammatory changes associated with abnormal anal sacs, and to counteract the offensive odor of anal sac secretions. ... (3) For use only by or on the order of a licensed veterinarian.
Fluocinolone acetonide, dimethyl sulfoxide otic solution. (a) Specifications. Each milliliter of solution contains 0.01 percent of fluocinolone acetonide in 60 percent dimethyl sulfoxide with propylene glycol and citric acid. ... (c) Conditions of use. (1) The drug is used in dogs for the relief of pruritis and inflammation associated with acute and chronic otitis. ... (3) There should be careful initial evaluation and followup of infected ears. Incomplete response or exacerbation of corticosteroid-responsive lesions may be due to the presence of an infection which requires identification or antibiotic sensitivity testing, and the use of the appropriate antimicrobial agent. As with any corticosteroid, animals with a generalized infection should not be treated with this product without proper supportive antimicrobial therapy. Preparations with dimethyl sulfoxide should not be used in pregnant animals. For use by or on the order of a licensed veterinarian.
【Reactivities and Incompatibilities】
Can react with oxidizing materials.
Violent or explosive reaction with many acyl, aryl, and nonmetal halides (eg acetyl chloride, benzenesulfonyl chloride, bromobenzoyl actanilide, cyanuric chloride, iodine pentafluoride, Mg(ClO4)2, CH3Br, NiO4, oxalyl chloride, P2O3, phosphorus trichloride, phosphoryl chloride, silver fluoride, silver difluoride, sodium hydride, sulfur dichloride, disulfur dichloride, sulfurylchloride, tetrachlorosilane, and thionyl chloride).
Violent or explosive reaction with boron compounds (eg borane, nonahydrononaborate (2-) ion), 4(4'-bromobenzoyl)acetanilide, carbonyl diisothiocyanate, dinitrogen tetraoxide, hexachlorocyclotriphosphazine, copper + trichloroacetic acid, metal alkoxides (eg potassium tert-butoxide, sodium isopropoxide), trifluoroacetic acid anhydride.
Incompatible with magnesium perchlorate, metal oxosalts, perchloric acid, periodic acid, sulfur trioxide.
Forms powerfully explosive mixtures with metal salts of oxoacids (eg aluminum perchlorate, sodium perchlorate, and iron (III) nitrate).
【Other Preventative Measures】
... DMSO can be harmful. ... Use effective fume removal device.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
... Based on chemical and physical properties alone, /dimethyl sulfoxide/ is ranked 10th/ of the ten most potentially irritating solvents /From table/.

? Dimethyl sulfoxide with a CAS number of 67-68-5. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, so that one may taste it soon after it comes into contact with the skin. Its taste has been described as oyster- or garlic-like.
Chemical Stability of Dimethyl sulfoxide (CAS NO. 67-68-5): Stable under normal temperatures and pressures. Hygroscopic: absorbs moisture or water from the air.
Conditions to Avoid: Incompatible materials, exposure to moist air or water.
? Dimethyl sulfoxide is incompatibilities with Other Materials Strong oxidizing agents, perchloric acid.
Hazardous decomposition products of?Dimethyl sulfoxide are carbon monoxide, oxides of sulfur, carbon dioxide, formaldehyde.
Hazardous polymerization of Dimethyl sulfoxide will not occur.

【Octanol/Water Partition Coefficient】
log Kow = -1.35
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

In industry, DMSO is produced by catalytic oxidation of dimethyl sulfide with oxygen or by oxidation with nitrogen dioxide. The oxidation of dimethyl sulfide with oxygen at 7.2 MPa and 105 deg C gives good yields of DMSO.
Usually obtained as a by-product of paper manufacture... .
Oxidation of dimethyl sulfide with nitrogen tetroxide under anhydrous conditions; sulfide waste liquors
U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686; Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438;
(1972) Probably greater than 4.54x10+5 g
(1975) probably greater than 4.54x10+5 g


Biomedical Effects and Toxicity

【Biological Activity】
Solvent with wide ranging applications in biological research.
【Pharmacological Action】
- Substances that provide protection against the harmful effects of freezing temperatures.
- Substances that influence the course of a chemical reaction by ready combination with free radicals. Among other effects, this combining activity protects pancreatic islets against damage by cytokines and prevents myocardial and pulmonary perfusion injuries.
- Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed)
【Therapeutic Uses】
Analgesics, Non-Narcotic; Anti-Inflammatory Agents, Topical; Cryoprotective Agents; Excipients; Free Radical Scavengers; Solvents
Dimethyl sulfoxide is indicated for the symptomatic relief of interstitial cystitis. /Included in US product labeling/
Dimethyl sulfoxide administered topically, orally, or intravenously has NOT been proven to be effective in the treatment of musculoskeletal disorders; diseases of connective tissue (e.g., osteoarthritis, rheumatoid arthritis, cutaneous manifestations of scleroderma, gout, ankylosing spondylitis); viral, bacterial, fungal, or parasitic infections of the skin; burns; postoperative pain; wounds (to promote healing); or mental conditions. However, investigational studies are being conducted on the transcutaneous carrier properties of dimethyl sulfoxide and on the efficacy of dimethyl sulfoxide in scleroderma, head injury, stroke, spinal cord trauma, arthritis, trauma of acute injuries, such as sprains and strains, and other disorders.
MEDICATION (VET):Topically to reduce swelling due to trauma.
MEDICATION (VET):... Analgesic, antiinflammatory. Use: in USA currently under special permission by FDA, since its enhancement of percutaneous absorption, analgesia, and antiinflammatory benefits were not without some untoward effects. ... Topical use has reduced mammary gland swellings in dogs and tendinitis in horses and dogs, etc. Parenteral use has reduced mortality from panleukopenia in cats.
/Exptl therapy:/ Accidental subcutaneous extravasation of several antineoplastic agents may provoke skin ulcerations for which there has been no simple and effective treatment. Since January 1983 all patients in an institution sustaining extravasation by a cytotoxic drug have been treated with a combination of dimethyl sulfoxide and alpha-tocopherol. During the first 48 hr after extravasation a mixture of 10% alpha-tocopherol acetate and 90% dimethyl sulfoxide was topically applied. The bandage was changed every 12 hr. So far eight patients with extravasation of an anthracycline or mitomycin were treated on this protocol. No skin ulceration, functional or neurovascular impairment occurred in any of these patients. The only toxic effect observed by this treatment was a minor skin irritation. The combination of dimethyl sulfoxide and alpha-tocopherol seems to prevent skin ulceration induced by anthracyclines and mitomycin. [Ludwig CU et al; Eur J Cancer Clin Oncol 23 (3): 327-9 (1987)]
【Biomedical Effects and Toxicity】
Following topical application, DMSO is absorbed and widely distributed in tissue and body fluids. DMSO and dimethyl sulfone are excreted in the urine and feces. DMSO is eliminated through the breath and skin and is responsible for the characteristic garlic odor. ... Dimethyl sulfone can persist in serum > 2 weeks after a single intravesical instillation. No residual accumulation of DMSO has occurred after treatment from protracted periods of time.
Dimethyl sulfoxide and one of its metabolites, dimethyl sulfone, are excreted in the urine and feces. The other metabolite, dimethyl sulfide, is eliminated via breath and through the skin.
It is not known whether dimethyl sulfoxide is excreted in breast milk and problems in humans have not been documented
In man radioactivity of 35S DMSO appeared in blood 5 min after cutaneous application. One hour later, radioactivity could detected in bones.
DMSO was administered orally /to human volunteers/ at a dose of 1g/kg as a 70% aqueous solution; a dose of 1 g/kg was administered dermally. DMSO was readily absorbed when administered dermally, peak serum levels occurring after 4 to 8 hr. Orally administered DMSO was rapidly absorbed, reaching a peak serum level in 4 hr. Serum levels of DMSO were undetectable after 120 hr. Both unchanged DMSO and a metabolite, dimethylsulfone (DMSO2) were isolated from urine. Dimethylsulfone appeared in serum after about 48 hr and persisted for as long as 400 hr. Urinary excretion of DMSO after dermal and oral administration amounted to approximately 13% and 30-68% of the dose, respectively. Excretion of DMSO2 was about 5 to 10% and 21 to 23%, respectively.
S35-DMSO was administered to rats orally, animals were killed at various times and the tissues were assayed for total radioactivity. There were appreciable concentrations of radioactivity in all tissues 0.5 hr after an oral dose. Plasma, kidney, spleen, lung,heart and testes appeared to have somewhat higher levels than liver, fat, small intestine, brain, skeletal muscle and red cells. Concentrations in the testes, brain skeletal muscle and heart increased after 0.5 hr, but remained virtually constant in other tissues. Levels had declined to minimal values in all tissues after 24 hr. ... The ratio of DMSO2 to DMSO in rats 4 hr after oral administration of S35-DMSO was found to be virtually constant in liver, testes, kidney, spleen, small intestine, heart and plasma, averaging about 6.5% (range of 4.1-10.6% for tissues of 2 rats).
The rate of passage of dermally applied S35-DMSO through the skin was also estimated in rats and rabbits. Eight rats were dosed dermally with 0.55 g/kg of S35-DMSO. Two animals each were sacrificed after 30 min, 1 hr, 2 hr and 24 hr respectively. In rats, after 30 min, 63% (average) of the dose remained at the site of application; after 1 hr, 19% (average) of the dose remained; and, after 2 hr, 14% (average) was left. After 24 hr, the radioactivity at the site of application was the same as that of the surrounding skin. Six rabbits were similarly treated. In 2 animals, sacrificed after 30 min, 85% (average) of the dose remained at the site of application. After 4 hr, 11% (average) remained, and, after 24 hr, the radioactivity was essentially equal to that of the surrounding skin. Radioactivity in respired air was measured from 2 rats given 0.55 g/kg of S35-DMSO (approximately 8 uC) dermally. An average of 6.0% of the dose was found in the respired air.
Urinary excretion of DMSO /in monkeys/ increased rapidly, reached a steady state level of approximately 9 gms/day after 2 days. The increase in DMSO excretion at 5 days reflected an increased urine volume on that day. DMSO disappeared rapidly from urine after treatment ended and only trace amounts were detected after 72 hrs. About 128 gms, or 60% of the ingested DMSO was excreted in the urine unchanged. ... Urinary excretion of DMSO2 increased slowly and reached a maximum of about 3 gms/day after 5 days of DMSO Administration. Excretion remained between 2-3 gms/day during the remainder of oral DMSO. Once DMSO treatment stopped, urinary DMSO2 declined slowly over the next 5 days. Approximately 33 gms, or about 16% of the ingested DMSO was excreted in urine as DMSO2.
Plasma concentrations of DMSO, dimethylsulfone (DMSO2), and dimethylsulfide (DMSH2) were assessed in 10 patients who underwent autologous transplants with stem cells, cryopreserved in 10% DMSO (vol/vol). Blood was sampled at multiple times after the stem-cell infusion. Urine was pooled during the 24 hours postinfusion. DMSO, DMSO2, and DMSH2 were assayed simultaneously by gas chromatography. A one-compartment model with saturable elimination proved most suitable for fitting plasma DMSO concentration-versus-time data. Stem-cell volumes infused ranged between 180 and 585 mL (254 to 824 mmol DMSO). Infusions lasted between 20 and 120 minutes. Peak plasma DMSO concentrations were 19.1 +/- 6.3 mmol/L (mean +/- SD). Pharmacokinetic parameters for volume of the central compartment (Vc), maximum velocity (Vmax), and Michaels-Menten constant (Km) were 37.3 +/- 17 L, 0.99 +/- 0.57 mmol/L/hr, and 5.2 +/- 5.0 mmol/L, respectively. Plasma DMSO2 concentrations increased during the first 24 hours, plateaued at 4.4 +/- 1.2 mmol/L, and remained there until 48 hours (the last sample). DMSH2 concentrations were at steady-state by 5 minutes and remained between 3 and 5 mmol/L for 48 hours. Urinary excretion of DMSO and DMSO2 accounted for 44% +/- 4% and 4% +/- 1%, respectively, of the administered DMSO dose. Renal clearance of DMSO was 14.1 +/- 3.4 mL/min. These data (1) document plasma concentrations of DMSO and metabolites in patients following peripheral-blood stem-cell transplants; (2) allow consideration of potential effects of these concentrations on stem-cell engraftment and drug-drug interactions; and (3) can facilitate a concentration-guided phase I trial of DMSO. [Egorin MJ et al; J Clin Oncol. 16(2): 610-5 (1998)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a log Kow of -1.35(2) and a regression-derived equation(3), indicates that dimethyl sulfoxide is expected to have very high mobility in soil(SRC). Volatilization of dimethyl sulfoxide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.5X10-9 atm-cu m/mole(4). Dimethyl sulfoxide is not expected to slowly volatilize from dry soil surfaces(SRC) based upon a vapor pressure 6.1X10-1 mm Hg(5). After 14 days incubation with an activated sludge inoculum(6), a theoretical BOD of 3% indicates that biodegradation may not be an important environmental fate process in water(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a log Kow of -1.35(2) and a regression-derived equation(3), indicates that dimethyl sulfoxide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(SRC) based upon a Henry's Law constant of 1.5X10-9 atm-cu m/mole(4). According to a classification scheme(5), bioconcentration studies resulting in BCF
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl sulfoxide, which has a vapor pressure of 1.6X10-1 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the atmosphere. In the atmosphere, two reported reaction rate constants for the reaction of dimethyl sulfoxide with photochemically-produced hydroxyl radicals are 6.2X10-11 cu cm/molecule-sec(3) and 5.9X10-11 cu cm/molecules-sec(4), corresponding to half-lives of 6.6 and 6.2 hrs, respectively, at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm. Dimethyl sulfoxide does not absorb light at wavelengths >290 nm(5) and therefore is not expected to be susceptible to direct photolysis by sunlight.

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