Methylsulfonylmethane

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Methylsulfonylmethane
Image:Dimethylsulfone Structure.png
General
Systematic name dimethylsulfone
Other names methyl sulfone
methylsulfonylmethane
sulfonylbismethane
DMSO2
MSM
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 (? K)
Boiling point 238 °C (? K)
Viscosity  ? cP at ? °C
Hazards
MSDS External MSDS
Main hazards  ?
NFPA 704
Image:Nfpa h1.png Image:Nfpa f1.png Image:Nfpa r0.png
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

Methylsulfonylmethane (MSM, or dimethylsulfone) is an organic sulfur compound with the chemical formula CH3SO2CH3. It belongs to a class of compounds known as sulfones. It is found naturally in some primitive plants and is present in small amounts in many foods and beverages.

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.

MSM is also known as dimethylsulfone, or DMSO2, a name that reflects its close metabolic relationship to dimethyl sulfoxide (DMSO). MSM is the primary metabolite of DMSO in humans, and it shares some of its parent compound’s properties. According to law enforcement officials [1], MSM is also used to dilute methamphetamine in the illegal drug trade in the United States.

MSM is marketed as a dietary supplement. However, the claims of proof of its beneficial effects are disputed and published research on the compound's effects is considered thin.

Contents

Claims of beneficial effects

MSM has been purported to have anti-inflammatory (Hasegawa, 2004; Childs, 1994; Murav'ev IuV et al, 1991; Parcell, 2002; Usha & Naidu, 2004) and anti-cancer (McCabe et al, 1986; O'Dwyer et al, 1988; Ebisuzaki, 2003; Wang et al, 2003a; Wang et al, 2003b) properties and to inhibit prostacyclin (PGI2) synthesis in cultured cells of the endothelium (Alam & Layman, 1983; Layman, 1987), an action that is believed to combat atherosclerosis. The therapeutic action of dimethyl sulfoxide (DMSO) may be mediated, at least in part, by MSM (Gerhards & Gibian, 1967; Williams et al, 1966; Kocsis et al, 1975; Jacob & Appleton, 2003).

Animal studies

In an experimental model of spontaneous arthritis in mice, oral MSM decreased joint degeneration (Murav-ev et al, 1991). In a mouse rheumatoid arthritis model, oral MSM decreased proliferation of the synovium, inflammation and auto[antibody] titers (Moore & Mortoin, 1985). A similar regimen in experimental lupus erythematosus in mice showed a reduced antinuclear antibodies and reduced incidence of anemia, while protecting against kidney damage (Morton & Moore, 1986). Oral MSM also modified immune responses, reducing arthritis deformities and swelling induced by collagen injections in mice, indicating a potential role for MSM in treating rheumatoid arthritis (Hasegawa, 2004). Several animal studies suggest a role for MSM in the prevention of breast cancer (McCabe et al, 1986; Wang et al 2003a; Wang et al 2003b) and colon cancer (O'Dwyer et al, 1988).

Human studies

Stanley W. Jacob, M.D., F.A.C.S. of the Oregon Health & Science University claims to have treated over 18,000 patients with MSM. Dr. Jacob claims to have successfully treated with MSM include osteoarthritis, rheumatoid arthritis, chronic pain syndromes, repetitive stress injuries (e.g., carpal tunnel syndrome, tendinitis, bursitis), scleroderma, lupus erythematosus, interstitial cystitis, fibromyalgia, myasthenia gravis, asthma, hayfever, snoring and many lesser-known clinical entities. (Jacob & Appleton, 2003; Jacob et al, 1999)

Arthritis: A double-blind study of MSM for osteoarthritis, patients with knee osteoarthritis received either 1,500 mg MSM, 1,500 mg glucosamine sulfate, 1,500 mg each of MSM and glucosamine sulfate, or placebo; significant decreases in the Lequesne Index were reported with MSM, glucosamine sulfate and their combination.

Seasonal Allergic Rhinitis: The first clinical study of oral MSM to be published in a peer-reviewed medical journal evaluated the efficacy of MSM for hayfever (Barrager et al, 2002). Fifty subjects completed the open-label study. Participants consumed 2,600 mg of MSM (OptiMSM, Cardinal Nutrition, Vancouver, WA) orally per day for 30 days. A Seasonal Allergy Symptom Questionnaire (SASQ) was used to evaluate clinical respiratory symptoms and energy levels at baseline and on days 7, 14, 21 and 30. Immune and inflammatory reactions were measured by plasma IgE and C-reactive protein at baseline and on day 30. Day 7 upper and total respiratory symptoms were reduced significantly from baseline. Lower respiratory symptoms were significantly improved from baseline by week 3. All respiratory improvements were maintained through the 30-day visit. Energy levels increased significantly by day 14; this increase continued through day-30.

Interstitial cystitis: In 1978, the FDA approved a 50-percent dilution of MSM for instillation into the bladder as a treatment for interstitial cystitis. ([2], citing [3].) Stacy J. Childs, M.D., then of the University of Alabama-Tuscaloosa and now practicing in Cheyenne, Wyoming, published a case series describing the successful intravesicular use of MSM use among interstitial cystitis patients who had not been helped by standard medical treatments. The report was published in 1994 in the Urologic Clinics of North America.

Snoring: Blum & Blum conducted a randomized, double-blind, placebo controlled clinical trial of an MSM-containing throat spray for snoring (Blum & Blum, 2004).

Toxicity

Clinical experience indicates that MSM may be used for prolonged periods without serious toxicity. According to Dr. Jacob, for more than two decades, thousands of people came to the DMSO Clinic at the Oregon Health & Science University (OHSU) and received upwards of 100 grams per day of MSM without serious side effects. In total, Dr. Jacob claims to have treated some 18,000 patients with MSM. (Jacob & Appleton, 2003)

MSM appears to have no significant acute toxicity in laboratory tests. The LD50 (dose at which 50% of test subject are killed) of MSM is > 17.5 grams per kilogram of body weight. In the first and only toxicity study of MSM to be published in a peer-reviewed scientific journal, both the acute and subchronic oral toxicity of MSM in rats were studied; no adverse effects, clinical signs of toxicity, or mortalities were observed at doses of 2 grams/kilogram body weight per day. In a 90-day follow-up study rats received daily oral doses of 1.5 g/kg of MSM. The animals were assessed by hematology, clinical chemistry, clinical symptom observation and gross pathology. No deaths occurred, and no changes related to the administration of MSM were noted in any of the parameters examined. (Horvath et al, 2002)

Three nuclear magnetic resonance studies (Rose et al, 2000; Lin et al, 2001; Cecil et al, 2002) have found that MSM appears to cross the blood-brain barrier. However, none of these studies reported any neurotoxicity. A fourth NMR study demonstrated that MSM is a "regular" constituent of cerebrospinal fluid and plasma, noting that it derives from dietary sources, intestinal bacterial metabolism, and from human endogenous methanethiol metabolism (Engelke et al, 2005).

Dose

MSM supplement manufacturers typically suggest doses for use as a dietary supplement ranging from 2 to 10 grams per day. Higher amounts appear to be safe, although some people do experience loose stool or abdominal discomfort when too much is taken at once. (Jacob & Appleton, 2003; Jacob et al, 1999; Parcell, 2002).

Manufacturing and purity

After the reaction phase (DMSO + Hydrogen Peroxide yields MSM + water), MSM must be stripped of water and purified. There are two methods of purification currently used in commercial production of MSM as a dietary supplement: crystallization and distillation. The comparative advantages and disadvantages of these methods can be stated as follows: Distillation produces a product of superior purity, but it is more expensive and therefore fewer manufacturers invest in it; crystallization yields product with varying degrees of purity, but it is a more cost-effective method of production and is thus preferred by manufacturers making cheaper MSM.

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 may therefore be present in crystallized MSM. This is a concern when MSM is manufactured in countries where water pollution is problematic, like China.

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. The less water present in a product, the less water quality is a concern. Heavy metals, which are removed from the still bottoms, cannot be removed by crystallization. Because potential contaminants have unique boiling points that are different from that of MSM, they are all removed by distillation. Purity of distilled MSM is, therefore, not dependent on water quality.

Many brands of MSM claim to be 99.9% pure, but that figure can be misleading. Purity is usually assessed in these cases using high resolution gas-liquid chromatography (HRGC), but this technique only measures volatile purity. Contaminants in the MSM that cannot be volatilized (e.g., heavy metals) would not show up on this test result. So unless other purity tests are performed, that figure is meaningless. The answers to the purity question, unfortunately, do not appear on the supplement label. It requires contacting the manufacturer and requesting data from the Certificate of Analysis on the raw material

One such test is melting point. The presence of contaminants changes the melting point of MSM, either by raising or lowering it. MSM should melt at 109.5 degrees Celsius, give or take one degree. It is a narrow range, as it should be, and the one degree leeway is really only given to account for lab-to-lab differences in equipment calibration. Variations in melting point more than a degree up or down are indicative of the presence of contaminants; specifically, non-volatile contaminants like heavy metals.

MSM should also be free of residual DMSO, a raw material used in its manufacture. DMSO is regulated as a drug in the United States.

MSM should also be tested for microbiological contaminants and heavy metals. Because MSM is taken in gram dosages, lead content should be as low as analytical laboratory detection methods permit (0.01 parts per million).

References

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