METHYLSULFONYLMETHANE (MSM)

Methylsulfonylmethane (MSM) is an organosulfur compound that serves as a highly bioavailable source of sulfur for the body.
Methylsulfonylmethane (MSM) is widely used in formulations supporting joint health, connective tissues, and skin, hair, and nail care.
Methylsulfonylmethane (MSM) is highly stable and easily incorporated into dietary supplements, cosmetics, and functional formulations due to its neutral properties.

CAS Number: 67-71-0
EC Number: 200-665-9
Molecular Formula: C2H6O2S
Molecular Mass: 94.13 g/mol

Synonyms: Dimethyl sulfone, Methyl sulfone, MSM, DMSO2, Sulfonylbismethane, Dimethyl sulphone, Crystalline MSM, Organic sulfur, Methylsulfonyl methane, Methyl sulphonyl methane

Methylsulfonylmethane (MSM) is an organosulfur compound widely used in nutraceutical, food supplement, cosmetic, and personal care applications.
Methylsulfonylmethane (MSM) is valued as a bioavailable sulfur source and is typically supplied as a white crystalline powder with good stability under normal storage conditions.
Methylsulfonylmethane (MSM) is especially recognized in formulations developed for joint support, connective tissue health, skin care, and wellness products.

Methylsulfonylmethane (MSM) is an organosulfur compound with the formula (CH3)2SO2.
Methylsulfonylmethane (MSM) is also known by several other names including methyl sulfone and (especially in alternative medicine) Methylsulfonylmethane (MSM).

This colorless solid features the sulfonyl functional group and is the simplest of the sulfones.
Methylsulfonylmethane (MSM) is relatively inert chemically and is able to resist decomposition at elevated temperatures.

Methylsulfonylmethane (MSM) occurs naturally in some primitive plants, is present in small amounts in many foods and beverages, and is marketed as a dietary supplement.
Methylsulfonylmethane (MSM) is sometimes used as a cutting agent for illicitly manufactured methamphetamine.

Methylsulfonylmethane (MSM) is also commonly found in the atmosphere above marine areas, where it is used as a carbon source by the airborne bacteria Afipia.
Oxidation of dimethyl sulfoxide produces the sulfone, both under laboratory conditions and metabolically.

Methylsulfonylmethane (MSM) is a naturally occurring compound found in various foods and plants.
Methylsulfonylmethane (MSM) is a sulfur-containing compound that is often used as a dietary supplement.

Methylsulfonylmethane (MSM) is known for its potential health benefits, particularly in relation to joint health, inflammation, and pain relief.
Methylsulfonylmethane (MSM) is commonly marketed as a remedy for osteoarthritis and other inflammatory conditions.

Methylsulfonylmethane (MSM) is a naturally occurring organosulfur compound that can be found in several plants, grains, fruits, and vegetables.
In the 1970s, two chemists, Drs. Robert Herschler and Stanley Jacob, experimented extensively with the compound looking for possible clinical and therapeutic uses.
In the early 1980s Dr. Hershler patented the compound for many things including skin softening, nail strengthening, and stress relief.

Methylsulfonylmethane (MSM)'s mechanism of action is unclear, but it is thought to have influence on some processes that involve inflammation and oxidative stress at the subcellular level.
There are several published animal and human studies that have investigated Methylsulfonylmethane (MSM)'s potential for a variety of ailments and conditions.

Some studies included testing for improved skin quality, seasonal allergies, range of motion and physical function, arthritis, and inflammation.
Results from these studies have been variable, but there seems to be some evidence to support possible benefits in improving symptoms of osteoarthritis such as stiffness, swelling, and pain.

Uses of Methylsulfonylmethane (MSM):
Methylsulfonylmethane (MSM) is used in dietary supplements, capsules, tablets, functional powders, sports nutrition products, beauty-from-within formulations, and topical personal care products.
Methylsulfonylmethane (MSM) is commonly incorporated into joint support blends with glucosamine, chondroitin, or collagen.
In cosmetic applications, Methylsulfonylmethane (MSM) may be used in skin and hair care products aimed at conditioning and overall appearance support.

Methylsulfonylmethane (MSM) is commonly used for osteoarthritis, but may also benefit in alleviating GI upset, musculoskeletal pain, and allergies; boosting the immune system; and fighting microbial infections.
Clinical trials are needed to verify these potential uses.

Use as a solvent:
Because of its polarity and thermal stability, molten Methylsulfonylmethane (MSM) has been used industrially as a high-temperature solvent.
For example, displacement of aryl chlorides by potassium fluoride has been conducted in the liquid.

With a pKa of 31, the sulfone can be deprotonated with sodium amide.
The conjugate base has been used as a nucleophile.

Medical and dietary use:
Methylsulfonylmethane (MSM) is marketed as a dietary supplement with medical claims ranging from anti-inflammatory effects for pain management, skin condition and aging treatments, and immune system modulation.
No medical uses for Methylsulfonylmethane (MSM) have been approved and there is limited evidence to support most of the claims.
Small studies of Methylsulfonylmethane (MSM) have suggested some benefit for treatment of oxidative stress and osteoarthritis, but evidence for other uses is lacking.

Osteoarthritis:
Methylsulfonylmethane (MSM) may or may not be useful for osteoarthritis (OA) knee pain relief.
Methodological issues with the clinical trials prevent firm conclusions, and the review authors stated: "No definitive conclusion can currently be drawn" and there is "no definitive evidence that Methylsulfonylmethane (MSM) is superior to placebo in the treatment of mild to moderate osteoarthritis of the knee."

Oxidative stress and inflammation:
Multiple human and animal trials indicate Methylsulfonylmethane (MSM) may reduce oxidative stress and inflammation.

Uses and Pharmacology:
The sulfur content of Methylsulfonylmethane (MSM) can be used by the body to maintain normal connective tissues.
Methylsulfonylmethane (MSM) has also exhibited possible anti-inflammatory, antiatherosclerotic, and chemopreventative activities along with free radical scavenging.

Methylsulfonylmethane (MSM) has been reported to alleviate allergies, arthritis, GI upset, musculoskeletal pain, and to boost the immune system.
Methylsulfonylmethane (MSM) also possesses antimicrobial effects against organisms such as Giardia lamblia, Trichomonas vaginalis, and some fungi.
The suggested mechanism is that Methylsulfonylmethane (MSM) may bind to surface receptor sites, blocking the interaction of parasite and host.

Osteoarthritis:
There are a limited number of clinical trials in osteoarthritis to guide the use of Methylsulfonylmethane (MSM), support its efficacy, and describe adverse effects.

A randomized, double-blind, parallel, placebo-controlled study compared oral Methylsulfonylmethane (MSM) with glucosamine and the combination of the 2 in 118 patients with mild to moderate osteoarthritis for a minimum of 6 months.
For 12 weeks, patients received either placebo (n = 28), Methylsulfonylmethane (MSM) 500 mg 3 times daily (n = 30), glucosamine 500 mg 3 times daily (n = 30), or 500 mg each of Methylsulfonylmethane (MSM) and glucosamine 3 times daily (n = 30).

The primary outcome was the reduction of pain intensity assessed by a visual analogue scale (VAS).
Pain, swelling, and joint mobility were also scored on a 0 to 3 scale, with 3 as the most severe.

The primary outcome was not reported; however, all groups except for placebo experienced statistically significant improvements in pain and swelling.
The combination of glucosamine and Methylsulfonylmethane (MSM) showed statistically significant decreases in pain and swelling compared with either single treatment alone.

A 12-week pilot, randomized, double-blind, placebo-controlled clinical trial (n = 40) was conducted in patients with knee osteoarthritis, classified by American College of Rheumatology (ACR) criteria as functional class I, II, or III, for at least 3 months.
Participants received 3 g of oral Methylsulfonylmethane (MSM) micropill (OptiMSM) twice daily (increasing to this dose over 1 week) or placebo.

The primary end points were the composite subscales in the Western Ontario and McMaster University Osteoarthritis Index VAS on pain, stiffness, physical function, and aggregated total symptoms (0 = no pain, 100 = worst pain).
After 12 weeks, there was a statistically significantly higher decrease in pain (−14.6 for Methylsulfonylmethane (MSM) group and −7.3 for placebo group, P = 0.041) and for physical function impairment (−15.7 for Methylsulfonylmethane (MSM) group and −8.8 for placebo group, P = 0.045).

A trial (n = 89) on the effects of the oral combination product AR7, which includes sternum collagen II, Methylsulfonylmethane (MSM), cetyl myristoleate, lipase, vitamin C, and bromelain, was conducted in osteoarthritis.
A decrease in the percentage of patients reported to have pain, stiffness, and tenderness in the treatment group was found after 3 months.

A randomized, double-blind, placebo-controlled, 6-month trial (n = 60) evaluated the benefit of Methylsulfonylmethane (MSM) 5 g/day plus boswellic acids 7.2 mg/day for knee OA diagnosed by ACR criteria, with grade 3 Kellgren andLawrenceradiographic staging.
Pain assessed by VAS was significantly worse in the treatment group compared with placebo at 2 months, and no significant difference between groups was seen at 6 months.

Joint function assessed by Lequesne index was not significantly different between groups at either 2 or 6 months.
The treatment group had significant reductions in anti-inflammatory drug use compared with baseline at 2 and 6 months, and these differences were also significantly lower than the placebo group.Notarnicola 2011

Rosacea:
Topical Methylsulfonylmethane (MSM) showed benefit in combination with silymarin to treat rosacea in 46 patients.
A statistically significant decrease in erythema, papules, and itch intensity occurred.
Methylsulfonylmethane (MSM) was theorized to be beneficial in rosacea due to strong photoprotective action along with antioxidant effects and desensitization of the skin to potential allergens.

Exercise muscle injury:
A small, randomized, placebo-controlled study (n = 18) evaluated the effectiveness of Methylsulfonylmethane (MSM) on exercise-induced muscle damage.
Healthy volunteers were randomized to receive 50 mg/kg of Methylsulfonylmethane (MSM) in 200 mL of water or placebo daily for 10 days.

Blood samples were drawn at baseline, and following supplementation and a 14 km run.
The group receiving Methylsulfonylmethane (MSM) had significant reductions in serum bilirubin and creatine kinase levels following exercise compared with placebo, and total antioxidant capacity was significantly higher in the Methylsulfonylmethane (MSM) group compared with placebo.Barmaki 2012

Ichthyosis:
There is 1 case study of a patient with unrelieved ichthyosis treated unsuccessfully with a variety of topical agents.
After treatment with an over-the counter skin care product olivamine, a product that combines amino acids, vitamins, antioxidants, Methylsulfonylmethane (MSM), and water-resistant silicones with surfactant-free phospholipid cleansers, the patient was completely clear of thickened scales and itching after 4 weeks.

Veterinarian Uses:
A 10-day course of Methylsulfonylmethane (MSM) also has been evaluated in 13 horses with chronic obstructive pulmonary disease, and no changes occurred in parameters, such as lung sounds, respiratory rate, heart rate, temperature, nasal discharge, or arterial blood gas.
However, Methylsulfonylmethane (MSM) exerted some protective effects on oxidative and inflammatory exercise-induced injury in 24 jumping horses when given daily for 6 weeks before and during competition.

Benefits of Methylsulfonylmethane (MSM):

The clinical and practical advantages of using Methylsulfonylmethane (MSM) include:

Natural Pain Relief:
Methylsulfonylmethane (MSM) is a natural alternative to over-the-counter pain medications.

Reduced Inflammation:
Methylsulfonylmethane (MSM) may help decrease inflammation, benefiting those with chronic inflammatory conditions.

Joint Health:
Methylsulfonylmethane (MSM) supports joint function and may improve mobility in individuals with arthritis.

Skin Improvement:
Some users report better skin health and appearance with Methylsulfonylmethane (MSM) supplementation.

Minimal Side Effects:
Compared to many pharmaceuticals, Methylsulfonylmethane (MSM) has a relatively low risk of side effects.

Mechanism of Action of Methylsulfonylmethane (MSM):
The mechanism of action underlying Methylsulfonylmethane (MSM)'s medical claims is not clear.
Some promoters suggest that most people do not consume enough sulfur.

There is no Dietary Reference Intake (DRI) or Daily Value established for sulfur, but Methylsulfonylmethane (MSM) is present in significant amounts in foods such as cruciferous vegetables, garlic, onions, asafoetida, legumes, nuts, seeds, plant milk, animal milk and eggs (both whites and yolks).
The claims for the need for sulfur supplementation originate with Robert Herschler, a biochemist who filed a patent for using Methylsulfonylmethane (MSM) as a dietary supplement in 1982.

Moreover, in cases involving topical therapeutics, the role of Methylsulfonylmethane (MSM) as an active agent, per se, versus its having a role in promoting skin permeation (in manner, akin to its solvent relative DMSO) must be characterized/controlled.

The biochemical effects of supplemental Methylsulfonylmethane (MSM) are poorly understood.
Some researchers have suggested that Methylsulfonylmethane (MSM) has anti-inflammatory effects.

The spectrum of biological effects of dimethyl sulfoxide (DMSO) and Methylsulfonylmethane (MSM) differ, but those of DMSO may be mediated, at least in part, by Methylsulfonylmethane (MSM).

Research of Methylsulfonylmethane (MSM):

Skin, hair, nails:
The first scientific investigation of Methylsulfonylmethane (MSM) for skin health was published in 2015.
The RCT used a 3g per day dose and included only 20 women.

Results showed significant improvements in the number and severity of facial wrinkles, firmness, tone and texture.
Another study evaluated doses of 1g and 3g and showed improvements in wrinkles, firmness, and hydration at both dose levels in 20 persons.

The same author published a study on Methylsulfonylmethane (MSM) for hair and nails from the same clinical trial.
The results showed improvements in hair shine, volume, and appearance, and nail shine and appearance.

An Italian study evaluated the effects of a nutraceutical composed of Methylsulfonylmethane (MSM), hyaluronic acid, and L-carnosine.
The results from RCT showed broad improvements in facial skin hydration and elasticity, as well as decreased sebaceous secretions.

Oxidative stress and inflammatory response:
In one small human trial, Methylsulfonylmethane (MSM) has been shown to protect muscles from damage by reducing the amount of oxidative stress damage incurred through exercise.
In a second small trial the total antioxidant capacity was significantly increased after taking Methylsulfonylmethane (MSM).

Studies in animals indicate a hepatoprotective effect of Methylsulfonylmethane (MSM) against several toxins including acetaminophen, paraquat, and carbon tetrachloride.
Animal models of experimental colitis and pulmonary hypertension indicate a protective effect as well.

Allergies and immunity:
Two studies have evaluated the effects of Methylsulfonylmethane (MSM) on allergic rhinitis.
A 2004 multi-centered, open-label clinical trial found that Methylsulfonylmethane (MSM) reduced both upper and lower respiratory symptoms associated with seasonal allergic rhinitis (SAR), and increased energy levels.

Methylsulfonylmethane (MSM) found no significant changes in IgE levels, although the duration of the study was not likely long enough to see changes.
An RCT evaluated three doses of Methylsulfonylmethane (MSM) and found that a 3g daily dose was most effective compared to 1g or 6g per day.

Daily use at 3g decreased allergy-associated symptoms, including itchy eyes, itchy nose, watery eyes, rhinorrhea, sneezing, and nasal obstruction.
The 3g dose also improved peak nasal inspiratory flow (PNIF) indicating improved breathing.
The study also evaluated an acute 12g dose and found significant improvements in all symptoms except itching eyes and sneezing, but not for PNIF.

Methylsulfonylmethane (MSM) has been shown to improve immune function markers.
RCT found that in blood samples taken after bouts of exhaustive exercise, there was a reduced response to an infectious stimulus in the placebo group, but the Methylsulfonylmethane (MSM) group maintained a robust response, indicating that Methylsulfonylmethane (MSM) protected against stress-induced immunosuppression.

The authors postulate that Methylsulfonylmethane (MSM)'s anti-inflammatory properties reduce the overstimulation of inflammatory cells during exercise, thus conserving their ability to respond to infections threats.
This is supported by in vitro research showing Methylsulfonylmethane (MSM) inhibits over-activation of white blood cells and has an anti-apoptotic effect.

History of Methylsulfonylmethane (MSM):
Most research on Methylsulfonylmethane (MSM) involves animal studies.
Methylsulfonylmethane (MSM) has been suggested for use as a food supplement and is available in the United States as a dietary supplement under the Dietary Supplement Health and Education Act.

Chemistry of Methylsulfonylmethane (MSM):
Methylsulfonylmethane (MSM) is a normal oxidation product of dimethyl sulfoxide (DMSO).
Unlike DMSO, Methylsulfonylmethane (MSM) is odor free and is a dietary factor.

Methylsulfonylmethane (MSM) has been referred to as "crystalline DMSO.
Methylsulfonylmethane (MSM) provides a dietary source of sulfur for methionine.
Methylsulfonylmethane (MSM)'s medicinal properties are theorized to be similar to DMSO, without the odor and skin irritation complications.

Handling and Storage of Methylsulfonylmethane (MSM):

Handling:
Avoid generating excessive dust during use.

Storage:
Store in a cool, dry, well-ventilated place.

Container:
Keep container tightly closed when not in use.

Protection:
Protect from moisture.
Protect from contamination.

Stability and Reactivity of Methylsulfonylmethane (MSM):

Chemical stability:
Stable under normal handling and storage conditions.

Reactivity:
No hazardous reactivity expected under normal conditions.

Conditions to avoid:
Excessive heat.
Moisture.
Contamination.

Incompatible materials:
Strong oxidizing agents.

Hazardous decomposition products:
Sulfur oxides (SOₓ) may form under fire conditions.
Carbon oxides (CO, CO₂) may be released.

First Aid Measures of Methylsulfonylmethane (MSM):

Inhalation:
Move to fresh air if dust is inhaled.

Skin contact:
Wash with soap and water.

Eye contact:
Rinse cautiously with water for several minutes.

Ingestion:
Rinse mouth.
Seek medical advice if discomfort occurs.

Firefighting Measures of Methylsulfonylmethane (MSM):

Suitable extinguishing media:
Water spray.
Foam.
Dry chemical.
Carbon dioxide (CO₂).

Hazards:
Thermal decomposition may produce sulfur oxides and carbon oxides.

Protective equipment:
Firefighters should use suitable protective equipment.

Accidental Release Measures of Methylsulfonylmethane (MSM):

Personal precautions:
Avoid dust formation.
Avoid unnecessary exposure.

Environmental precautions:
Prevent large releases into drains or waterways.

Cleanup methods:
Sweep or collect material.
Place in a suitable container for disposal.

Exposure Controls / Personal Protection of Methylsulfonylmethane (MSM):

Respiratory protection:
Use dust protection if airborne particles are generated.

Eye protection:
Safety glasses recommended.

Hand protection:
Protective gloves recommended for prolonged handling.

Hygiene measures:
Wash hands thoroughly after handling.

Identifiers of Methylsulfonylmethane (MSM):
Chemical name: Methylsulfonylmethane (MSM)
Common name: MSM
CAS number: 67-71-0
EC number: 200-665-9
Molecular formula: C2H6O2S
Molecular mass: 94.13 g/mol

CAS Number: 67-71-0
Abbreviations: MSM
Beilstein Reference: 1737717
ChEBI: CHEBI:9349
ChEMBL: ChEMBL25028
ChemSpider: 5978
ECHA InfoCard: 100.000.605
EC Number: 200-665-9
Gmelin Reference: 130437
KEGG: C11142
PubChem CID: 6213
RTECS number: PB2785000
UNII: 9H4PO4Z4FT
CompTox Dashboard (EPA): DTXSID4043937
InChI: InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
Key: HHVIBTZHLRERCL-UHFFFAOYSA-N
InChI=1/C2H6O2S/c1-5(2,3)4/h1-2H3
Key: HHVIBTZHLRERCL-UHFFFAOYAG
SMILES: [O-][S++]([O-])(C)C

Properties of Methylsulfonylmethane (MSM):
Chemical formula: (CH3)2SO2
Molar mass: 94.13 g·mol−1
Appearance: White crystalline solid
Density: 1.45 g/cm3
Melting point: 107–109 °C (225–228 °F; 380–382 K)
Boiling point: 248 °C (478 °F; 521 K)
Solubility in water: 187 g/L (30 °C (86 °F; 303 K))
log P: -1.41 (water / octanol)
Acidity (pKa): 31

Appearance: White crystalline powder
Odor: Odorless or nearly odorless
Solubility: Soluble in water
Chemical class: Organosulfur compound
Stability: Stable under normal conditions
Melting point: Approximately 108–111°C

Related compounds of Methylsulfonylmethane (MSM):
DMSO
Dimethyl sulfide
Dimethyl sulfate
Sulfolane

Names of Methylsulfonylmethane (MSM):

Preferred IUPAC name:
(Methanesulfonyl)methane

Other names:
Methane, 1,1'-sulfonylbis-dimethyl sulfone
Methyl sulfone
Sulfonylbismethane
DMSO2