Dimethyl sulfoxide
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Dimethyl sulfoxide

Dimethyl Sulfoxide (DMSO, molecular formula C2H6OS), also known as methyl sulfoxide, dimethyl sulphoxide, dimethylsulfoxide, methylsulfinylmethane or sulfinylbismethane, is a sulfur-containing organic compound. It is a clear, colorless hygroscopic liquid. When it is pure it has little odor, but impure samples smell strongly of dimethyl sulfide. DMSO belongs to the class of "dipolar aprotic solvents" which includes also dimethylformamide, dimethylacetamide and N-methyl-2-pyrrolidone. more...

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It is readily soluble into a wide range of organic solventes such as alcohols, esters, ketones, chlorinated solvents and aromatic hydrocarbons. It is also miscible in all proportions with water.

Dimethyl sulfoxide is a by-product of wood pulping and is frequently used as solvent in a number of chemical reactions. In particular DMSO proved to be an excellent reaction solvent for SN2 alkylations: it is possible to alkylate indoles with very high yields using potassium hydroxide as the base and a similar reaction also occurs with phenols. DMSO can be reacted with methyl iodide to form a sulfoxonium ion which can be reacted with sodium hydride to form a sulfur ylide. The methyl hydrogens of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the resultant anions by the sulfoxide group.

One of the leading suppliers of DMSO is the Gaylord company in the USA.

Uses

DMSO was discovered in 1867, but was not used commercially until after WWII. Other than its use as a solvent, both in organic synthesis and industrial applications (polymer chemistry, pharmaceuticals and agrochemicals), DMSO also makes a very good paint stripper: it is able to remove many paints from both wood and metal in a small amount of time. It is thought to be much safer than many of the other chemicals used as paint strippers, such as nitromethane and dichloromethane.

In organic synthesis, DMSO is used in the oxidation reactions, the Pfitzner-Moffatt oxidation and the Swern oxidation.

DMSO is also employed as a rinsing agent in the electronics industry and, in its deuterated form (DMSO-d6), is a useful solvent in NMR due to its ability to dissolve a wide range of chemical compounds and its minimal interference with the sample signals. In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs and tissues. It is particularly important in the freezing and long-term storage of Embryonic stem cells, which are often frozen in a mixture of 10% DMSO and 90% fetal calf serum.

Use of dimethylsulfoxide in medicine dates from around 1963, when a University of Oregon Medical School team, headed by Stanley Jacob, discovered it could penetrate deeply through the skin and other membranes without damaging them and could carry other compounds deep into a biological system. In fact, it is possible to perceive the taste of DMSO (onion or garlic-like) in a matter of seconds after contact with the skin. In the medical field DMSO is predominantly used as a topical analgesic, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory and an antioxidant. It has been examined for the treatment of an extraordinary number of conditions and ailments. The FDA has approved DMSO usage only for the palliative treatment of interstitial cystitis. Morover it is commonly used as a liniment for horses, although its use in humans is controversial.

Read more at Wikipedia.org


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ask the experts - migraines - Runner's knee - Methylsulfonylmethane
From Better Nutrition, 2/1/01 by Ray Sahelian

I suffer from migraine headaches and am curious to know if it has anything to do with my diet. Do certain foods cause migraines--what in them would trigger migraines?

answer

Many factors are involved in bringing on migraines, including genetics, diet, food allergies, stress, hormonal imbalances and fatigue. Diet and food allergies are suspected to be a culprit about 30 percent of the time.

Since improper circulation underpins migraines, try to increase your intake of omega-3 fats since they help prevent excess stickiness of platelets and work well as natural blood thinners.

Also, evaluate to see if certain foods trigger your migraine, particularly chocolate, milk, nuts, "cured" meats, hot dogs, aged cheese, fermented, pickled or marinated foods and cola drinks. Very cold foods can sometimes trigger headaches. Hypoglycemia can also trigger migraines, so eat small, frequent meals throughout the day. Finally, eliminate specific chemicals that may trigger migraines, such as tyramine (found in aged cheese and vinegar), phenylalanine, alcoholic drinks such as red wine, beer or whisky, food additives (sodium nitrate, monosodium glutamate [MSG], aspartame) and caffeine. Avoid MSG and use stevia instead of Nutrasweet (brand of aspartame).

I have had runner's knee throughout the past year, could it be chronic? I've tried to tone down my exercises; is there anything else I can do?

answer

Runner's knee refers to the softening of the cartilage of the knee cap and is caused when the kneecap does not track smoothly in its femoral groove (at the thigh bone). The symptoms of this include pain near the knee cap, usually felt after sitting, running/ walking downhill and during other bent-knee exercises. The pain increases gradually over a period of time, often a year or longer.

When recovering, avoid exercise that puts weight on a bent knee, especially downhill walking or running -- try swimming as an alternative. Always rest if there is pain and swelling. Use ice treatment for 15 minutes twice daily after activity to reduce pain and inflammation.

Small doses of aspirin, naproxen, or ibuprofen work well as anti-inflammatory agents, but for long term treatment, stretching and strengthening exercises for the quadriceps, hamstrings and calves is helpful; try straight-knee leg lifts.

Orthotic devices to correct abnormal foot mechanics may also help, as does exercising on soft surfaces. Glucosamine and chondroiton supplements may help; also keeping a balanced diet, with plenty of protein will help.

I heard of athletes taking MSM, and, also that it is good against arthritis. Can it be taken to prevent athletic injury, as well?

answer

Methylsulfonylmethane (MSM) is an odorless breakdown product of dimethyl sulfoxide (DMSO). It is available in capsules and tablets, and for application to the skin in a lotion, cream, or gel.

There are few peer-reviewed, double-blind studies on MSM published in mainstream scientific journals and none in which MSM was tested against any human ailment. Researchers have accumulated knowledge through their own unpublished experiences and clinical evaluations. Anecdotal reports by people who have taken MSM say that this nutrient helps certain people with arthritis, but in my opinion, there is much more research done with glucosamine and chondroitin. I seriously doubt, however, that MSM can prevent athletic injuries since the majority of these injuries are due to excessive mechanical stresses on joints, ligaments, and muscles and not due to a deficiency of a particular nutrient.

Ray Sahelian is the author of the newly published Mind Boosters: A Guide to Natural Supplements That Enhance Your Mind, Memory, and Mood (St. Martin's Press, 2000). See www.raysahelian.com, or write to him in care of Better Nutrition magazine, Sabot Publishing, 9 Riverbend Drive, South, Stamford CT 06907. He cannot answer questions by mail or telephone. "Ask the Experts" is intended for educational purposes only. If you have a medical problem, consult your physician.

COPYRIGHT 2001 PRIMEDIA Intertec, a PRIMEDIA Company. All Rights Reserved.
COPYRIGHT 2001 Gale Group

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