Methylsulfonylmethane
From Wikipedia, the free encyclopedia
| Methylsulfonylmethane | |
|---|---|
  |
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| General | |
| Systematic name | dimethylsulfone |
| Other names | methyl sulfone methylsulfonylmethane sulfonylbismethane DMSO2 |
| Molecular formula | C2H6O2S |
| SMILES | CS(C)(=O)=O |
| Molar mass | 94.13 g/mol |
| Appearance | white crystalline solid |
| CAS number | [67-71-0] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | miscible |
| Melting point | 109 °C (382 K) |
| Boiling point | 238 °C (511 K) |
| Viscosity | ? cP at ? °C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 |
1
1
0
|
| Flash point | 143 °C |
| R/S statement | R: S: 24/25 |
| RTECS number | PB2785000 |
| Related compounds | |
| Related sulfones | ? |
| Related compounds | DMSO dimethyl sulfide |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Methylsulfonylmethane (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.
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[edit] Use as a solvent
Because of its polarity and thermal stability, MSM is used industrially as a high-temperature solvent for both inorganic and organic substances. It is used as a medium for carrying out chemical reactions in polymerization processes as well as to make pharmaceuticals, agrochemicals, paint, coating materials and biocides. According to U.S. law enforcement officials, MSM is used to dilute methamphetamine in the illegal drug trade. [1]
[edit] Effects on health
The effects of supplemental methylsulfonylmethane in biology and medicine are poorly understood. Several researchers have suggested that MSM has anti-inflammatory effects (Morton et al. 1986; Childs, 1994; Murav'ev et al., 1991). Any health effects of dimethyl sulfoxide (DMSO) may be mediated, at least in part, by MSM (Williams et al, 1966; Kocsis et al, 1975). Stanley W. Jacob, M.D., of the Oregon Health & Science University claims to have used MSM to treat over 18,000 patients with a variety of ailments (Jacob & Appleton, 2003).
Clinical evidence for the usefulness of MSM is limited to animal studies and four published clinical studies in humans. These pilot studies of MSM have suggested some benefits, particularly for treatment of osteoarthritis. Further studies would be needed to test the usefulness of the chemical as a medical therapy.
[edit] 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 (Usha and Naidu 2004). 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 (Kim et al). 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. The authors cautioned that this short pilot study did not address the long-term safety and usefulness of MSM, but suggested that physicians should consider its use for certain osteoarthritis patients, and that long-term studies should be conducted (Kim et al. 2006).
- Seasonal Allergic Rhinitis: Barrager et al. evaluated the efficacy of MSM for hayfever (Barrager et al, 2002). 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 (Childs 1994).
- Snoring: Blum & Blum conducted a randomized, double-blind, placebo controlled clinical trial of an MSM-containing throat spray for snoring (Blum & Blum, 2004).
[edit] Pharmacology and toxicity
The LD50 (dose at which 50% of test subjects are killed) of MSM is greater than 17.5 grams per kilogram of body weight. In rats, no adverse events were observed after daily doses of 2 g MSM per kg of body weight. In a 90-day follow-up study rats received daily MSM doses of 1.5 g/kg, and no changes were observed in terms of symptoms, blood chemistry, or gross pathology (Horvath et al., 2002).
Nuclear magnetic resonance (NMR) studies have demonstrated that oral doses of MSM are absorbed into the blood and cross the blood-brain barrier (Rose et al., 2000; Lin et al., 2001). An NMR study has also found detectable levels of MSM normally present in the blood and cerebrospinal fluid, suggesting that it derives from dietary sources, intestinal bacterial metabolism, and the body's endogenous methanethiol metabolism (Engelke et al., 2005).
The published clinical trials of MSM did not observe any serious side-effects of treatment, but there are no peer-reviewed data on the effects of long-term use in humans.
[edit] Manufacturing and purity
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. Distillation produces superior purity MSM (King, 1980), 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.
The purity of MSM separated by crystallization is dependent upon the purity of the solvent and the raw materials used in manufacturing, and on the industrial hygiene procedures employed at the plant. As crystals grow in solution, they naturally form pockets, called occlusions, which entrap solvent within the crystal structure. Contaminants, such as heavy metals, may therefore be present in crystallized MSM. This is a concern when MSM is manufactured in countries where water pollution is a problem.
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).
[edit] References
- 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
- Blum JM, Blum RI. The effect of methylsulfonylmethane (MSM) in the control of snoring. Integrative Medicine 2004;3(6)24-30.
- Childs SJ. Dimethyl sulfone (DMSO2) in the treatment of interstitial cystitis. Urol Clin North Am 1994;21:85–8. PMID 8284850
- 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
- Horváth K, Noker PE, Somfai-Relle S, et al. Toxicity of methylsulfonylmethane in rats. Food Chem Toxicol 2002;40:1459–62. PMID 12387309
- Jacob SW, Appleton J. MSM-The Definitive Guide (Topanga, Freedom Press, 2003) ISBN 1-893910-21-0
- 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
- King CJ. Separation Processes, 2nd ed. New York, McGraw-Hill, 1980. ISBN 0-07-034612-7
- 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
- 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
- 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
- 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
- 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
- Pfiffner JJ, North HB. Dimethyl sulfone: A constituent of the adrenal gland. J Biol Chem 1940;134:781–2. PDF online.
- 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
- 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.
- Williams KIH, Burstein SH, Layne DS. Dimethyl sulfone: isolation from cows’ milk. Proc Soc Exp Biol Med 1966;122:865–6. PMID 5918965
- 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
