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Methylsulfonylmethane |
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General |
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Systematic name |
dimethylsulfone |
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Other names |
methyl sulfone
methylsulfonylmethane
sulfonylbismethane
DMSO2 |
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Molecular formula |
C2H6O2S |
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SMILES |
CS(C)(=O)=O |
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Molar mass |
94.13 g/mol |
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Appearance |
white crystalline solid |
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CAS number |
[67-71-0] |
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Properties |
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Density and phase |
? g/cm3, ? |
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Solubility in water |
miscible |
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Melting point |
109 °C (382 K) |
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Boiling point |
238 °C (511 K) |
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Viscosity |
? cP at ? °C |
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Hazards |
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MSDS |
External MSDS |
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Main hazards |
None Known |
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Flash point |
143 °C |
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R/S statement |
R:
S: 24/25 |
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Related compounds |
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Related sulfones |
? |
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Related compounds |
DMSO
dimethyl sulfide |
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Except where noted otherwise,
data are given for
materials in their standard state
(at 25 °C, 100 kPa) |
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Methyl Sulfonyl Methane
(MSM, or dimethylsulfone) is an organic
sulfur compound
belonging to a class of chemicals
known as sulfones. It occurs naturally in some primitive
plants and is present in small amounts in many foods and
beverages.
MSM is also known as dimethylsulfone, or DMSO2, a name
that reflects its close chemical relationship to
dimethyl sulfoxide (DMSO), which differs only in the
oxidation state of the sulfur atom. MSM is the primary
metabolite of DMSO in humans, and it shares some of the
properties of DMSO.
MSM is sold as a dietary supplement that is marketed
with a variety of claims and is commonly used (often in
combination with glucosamine and/or chondroitin) for
helping to treat or prevent osteoarthritis. Retail sales
of MSM as a single ingredient in dietary supplements
amounted to $115 million in 2003. However, clinical
research on the medical use of the chemical in people is
limited to a few pilot studies that have suggested
beneficial effects.
Evidence from clinical
trials
Osteoarthritis
After several reports that MSM
helped arthritis in animal models, a double-blind,
placebo-controlled study suggested that 1500 mg per day
MSM (alone or in combination with glucosamine sulfate)
was helpful in relieving symptoms of knee
osteoarthritis. Kim et al. then conducted a double-blind
clinical trial of MSM for treatment of patients with
osteoarthritis of the knee. Twenty-five patients took 6
g/day MSM and 25 patients took a placebo for 12 weeks.
Ten patients did not complete the study, and
intent-to-treat analysis was performed. Patients who
took MSM had significantly reduced pain and improved
physical functioning, without major adverse events. No
evidence of a more general anti-inflammatory effect was
found, as there were no significant changes in two
measures of systemic inflammation: C-reactive protein
level and erythrocyte sedimentation rate.
Seasonal Allergic Rhinitis
Barrager evaluated the efficacy of
MSM for hayfever. Twenty-five subjects consumed 2,600 mg
of MSM per day for 30 days, and a significant
improvement in symptoms was observed compared to those
taking a placebo. However, the study was not blinded.
Also, no significant changes were observed in two
indicators of inflammation (C-reactive protein and
immunoglobulin E levels). The authors suggest that MSM
is safe for short-term use and recommend that a larger,
double-blind study be performed to establish its
usefulness in treating symptoms of seasonal allergic
rhinitis.
Interstitial cystitis
In 1978, the FDA approved
dimethylsulfoxide (DMSO) for instillation into the
bladder as a treatment for interstitial cystitis. Since
DMSO is metabolized to MSM by the body, it is possible
that MSM is the active ingredient in DMSO treatments.
Snoring
Blum & Blum conducted a randomized,
double-blind, placebo controlled clinical trial of an
MSM-containing throat spray for snoring.
Manufacture of MSM
MSM is manufactured by oxidation of
DMSO with hydrogen peroxide (DMSO + Hydrogen Peroxide
yields MSM + water). The MSM must then be purified.
There are two methods of purification currently used in
commercial production of MSM as a dietary supplement:
crystallization and distillation.
|

Extreme Close-Up of Pure
MSM in it's crystalline state |
Distillation produces superior
purity MSM, but is a more expensive process.
Crystallization yields products with varying degrees of
purity, but it is a more cost-effective method and is
thus preferred by some manufacturers.
Distillation uses boiling point differentials to purify
the MSM mixture. First, water is vaporized; then MSM is
separated from “low boilers” (i.e., components with low
boiling temperatures). Further distillation yields the
pure MSM product. Components with high boiling
temperatures (e.g., heavy metals, salts) remain in the
bottom of the distillation vessel and are removed as
waste. Distillation yields a product of excellent
purity. The product is quite dry (typically < 0.05%
moisture) when distilled properly, so fewer
moisture-related problems occur, such as product
degradation and microbial contamination. Also, the less
water present in a product, the less water quality is a
concern. Thus, distillation can remove heavy metals from
raw materials and is not dependent on water quality.
Many brands of MSM claim to be 99.9% pure, but this
figure can be misleading. Purity is usually assessed in
these cases using high resolution gas-liquid
chromatography (HRGC), but this technique only measures
volatile substances. Contaminants in the MSM that cannot
be volatilized (e.g., heavy metals) would not show up on
this test result. Meaningful assessment of purity
therefore requires additional testing. One such test is
measurement of melting point. MSM should melt in a
narrow range at 109.5 degrees Celsius, give or take one
degree. Any deviation of the melting point outside this
range indicates the presence of non-volatile
contaminants.
Unfortunately, such information does not appear on the
supplement label. To obtain it requires contacting the
manufacturer and requesting data from the Certificate of
Analysis on the raw material. If measured, levels of
lead and other heavy metals should be as low as
analytical laboratory detection methods permit (0.01
parts per million).
Further Reading
-
Sulfur -
the 4th most abundant mineral in the human body
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Georges
Hareau and Philip Kocienski, "Dimethyl Sulfone" in
Encyclopedia of Reagents for Organic Synthesis 2001
John Wiley & Sons. DOI: 10.1002/047084289X.rd371
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Barrager
E, Veltmann JR, Schauss AG, Schiller RN. A
multi-centered, open label trial on the safety and
efficacy of methylsulfonylmethane in the treatment
of seasonal allergic rhinitis. J Altern
Complement Med 2002;8:167–74. PMID 12006124
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Blum JM,
Blum RI. The effect of methylsulfonylmethane (MSM)
in the control of snoring. Integrative Medicine
2004;3(6)24-30.
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Childs
SJ. Dimethyl sulfone (DMSO2) in the treatment of
interstitial cystitis. Urol Clin North Am
1994;21:85–8. PMID 8284850
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Engelke
UF, Tangerman A, Willemsen MA, Moskau D, Loss S,
Mudd SH, Wevers RA. Dimethyl sulfone in human
cerebrospinal fluid and blood plasma confirmed by
one-dimensional (1)H and two-dimensional (1)H-(13)C
NMR. NMR Biomed 2005 Aug;18(5):331-6. PMID
15996001
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Horváth
K, Noker PE, Somfai-Relle S, et al.
Toxicity of methylsulfonylmethane in rats. Food
Chem Toxicol 2002;40:1459–62. PMID 12387309
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Jacob SW,
Appleton J. MSM-The Definitive Guide
(Topanga, Freedom Press, 2003) ISBN 1-893910-21-0
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Kim LS,
Axelrod LJ, Howard P, Buratovich N, Waters RF.
Efficacy of methylsulfonylmethane (MSM) in
osteoarthritis pain of the knee: a pilot clinical
trial. Osteoarthritis Cartilage
2006;14(3):286–94. PMID 16309928
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King CJ.
Separation Processes, 2nd ed. New York,
McGraw-Hill, 1980. ISBN 0-07-034612-7
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Kocsis
JJ, Harkaway S, Snyder R. Biological effects of the
metabolites of dimethyl sulfoxide.
Ann N Y Acad Sci 1975;243:104–9. PMID 1055534
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Lin A,
Nguy CH, Shic F, Ross BD. Accumulation of
methylsulfonylmethane in the human brain:
identification by multinuclear magnetic resonance
spectroscopy. Toxicol Lett 2001;123:169–77.
PMID 11641045
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Morton
JI, Siegel BV. Effects of oral dimethyl sulfoxide
and dimethyl sulfone on murine autoimmune
lymphoproliferative disease. Proc Soc Exp Biol
Med 1986;183:227–30. PMID 3489943
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Murav'ev
IuV, Venikova MS, Pleskovskaia GN,
et al. [Effect of dimethyl sulfoxide and
dimethyl sulfone on a destructive process in the
joints of mice with spontaneous arthritis]. Patol
Fiziol Eksp Ter 1991;(2):37–9 [in Russian]. PMID
1881708
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Pearson
TW, Dawson HJ, Lackey HB. Natural occurring levels
of dimethyl sulfoxide in selected fruits,
vegetables, grains and beverages. J Agric Food
Chem 1981;29:1019–21. PMID 7309994
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Pfiffner
JJ, North HB. Dimethyl sulfone: A constituent of the
adrenal gland. J Biol Chem
1940;134:781–2. PDF online.
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Rose SE,
Chalk JB, Galloway GJ, Doddrell DM. Detection of
dimethyl sulfone in the human brain by
in vivo proton magnetic resonance
spectroscopy. Magn Reson Imaging
2000;18:95–8. PMID 10642107
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Usha PR,
Naidu MUR. Randomised, double-blind, parallel,
placebo-controlled study of oral glucosamine,
methylsulfonylmethane and their combination in
osteoarthritis. Clin Drug Invest
2004;24(6):353–63.
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Williams
KIH, Burstein SH, Layne DS. Dimethyl sulfone:
isolation from cows’ milk. Proc Soc Exp Biol Med
1966;122:865–6. PMID 5918965
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Williams
KIH, Burstein SH, Layne. Metabolism of dimethyl
sulfide, dimethyl sulfoxide, and dimethyl sulfone in
the rabbit. Arch Biochem Biophys
1966;117:84–7. PMID 5971744
Our MSM has been laboratory tested in
Australia and is certified to be 99.9% pure. |