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42-545: First produced in 1861 in Chicago by former magician John Austin Hamlin and his brother Lysander Butler Hamlin, it was primarily sold and used as a liniment for rheumatic pain and sore muscles, but was advertised as a treatment for pneumonia, cancer, diphtheria, earache, toothache, headache, and hydrophobia . It was made of 50–70% alcohol containing camphor , ammonia , chloroform , sassafras , cloves , and turpentine , and

84-601: A cryoprotectant , added to cell media to reduce ice formation and thereby prevent cell death during the freezing process. Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at −80 °C (−112 °F) or stored in liquid nitrogen safely. In cell culture, DMSO is used to induce differentiation of P19 embryonic carcinoma cells into cardiomyocytes and skeletal muscle cells . Use of DMSO in medicine dates from around 1963, when an Oregon Health & Science University Medical School team, headed by Stanley Jacob , discovered it could penetrate

126-507: A feeling of warmth within the muscle of the area they are applied to, typically acting as rubefacients via a counterirritant effect. Methyl salicylate , which is the analgesic ingredient in some heat rubs, can be toxic if used in excess. Heating pads are also not recommended for use with heat rubs, because the added warmth may cause overabsorption of the active ingredients. Liniments are commonly used on horses following exercise, applied either by rubbing on full-strength, especially on

168-443: A large chemical library ), is readily miscible with water and cell culture media , and has a high boiling point (this improves the accuracy of test compound concentrations by reducing room temperature evaporation). One limitation with DMSO is that it can affect cell line growth and viability, with low DMSO concentrations sometimes stimulating cell growth, and high DMSO concentrations sometimes inhibiting or killing cells. DMSO

210-464: A level exceeded in children exposed to DMSO during bone marrow transplant . DMSO disposed into sewers can cause odor problems in municipal effluents: waste water bacteria transform DMSO under hypoxic (anoxic) conditions into dimethyl sulfide (DMS) that has a strong disagreeable odor, similar to rotten cabbage. However, chemically pure DMSO is odorless because of the lack of C-S-C ( sulfide ) and C-S-H ( mercaptan ) linkages. Deodorization of DMSO

252-468: A manufacturer of the chemical warned that the death of an Irish woman after undergoing DMSO treatment for a sprained wrist may have been due to the treatment, although no autopsy was done, nor was a causal relationship established. Clinical research using DMSO was halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972. In 1978,

294-568: A mild oxidant. It forms the basis of several selective sulfonium-based oxidation reactions including the Pfitzner–Moffatt oxidation , Corey–Kim oxidation and the Swern oxidation . The Kornblum oxidation is conceptually similar. These all involve formation of an intermediate sulfonium species (R 2 S X where X is a heteroatom) Related to its ability to dissolve many salts, DMSO is a common ligand in coordination chemistry . Illustrative

336-465: A mixture of 10% DMSO, a freezing medium, and 30% fetal bovine serum . In the cryogenic freezing of heteroploid cell lines ( MDCK , VERO , etc.) a mixture of 10% DMSO with 90%  EMEM (70% EMEM + 30% fetal bovine serum + antibiotic mixture) is used. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cells . DMSO

378-435: A relatively high boiling point. DMSO is metabolised to compounds that leave a garlic -like taste in the mouth after DMSO is absorbed by skin. In terms of chemical structure, the molecule has idealized C s symmetry . It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom. Dimethyl sulfoxide

420-575: Is nucleophilic toward soft electrophiles and the oxygen is nucleophilic toward hard electrophiles. With methyl iodide it forms trimethylsulfoxonium iodide , [(CH 3 ) 3 SO]I: This salt can be deprotonated with sodium hydride to form the sulfur ylide : The methyl groups of DMSO are only weakly acidic, with a p K a = 35 . For this reason, the basicities of many weakly basic organic compounds have been examined in this solvent. Deprotonation of DMSO requires strong bases like lithium diisopropylamide and sodium hydride . Stabilization of

462-679: Is a medicated topical preparation for application to the skin. Some liniments have a viscosity similar to that of water; others are lotion or balm; still, others are in transdermal patches , soft solid sticks, and sprays. Liniment usually is rubbed into the skin, which the active ingredients penetrate. Liniments are typically sold to relieve pain and stiffness, such as from muscular aches and strains , and arthritis . These are typically formulated from alcohol , acetone , or similar quickly evaporating solvents and contain counterirritant aromatic chemical compounds, such as methyl salicylate , benzoin resin , menthol , and capsaicin . They produce

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504-533: Is a solid, which can limit its utility in some chemical processes (e.g. crystallization with cooling). In its deuterated form ( DMSO- d 6 ), it is a useful solvent for NMR spectroscopy, again due to its ability to dissolve a wide range of analytes, the simplicity of its own spectrum, and its suitability for high-temperature NMR spectroscopic studies. Disadvantages to the use of DMSO- d 6 are its high viscosity, which broadens signals, and its hygroscopicity , which leads to an overwhelming H 2 O resonance in

546-548: Is an effective paint stripper , being safer than many of the others such as nitromethane and dichloromethane . DMSO is used in polymerase chain reaction (PCR) to inhibit secondary structures in the DNA template or the DNA primers . It is added to the PCR mix before reacting, where it interferes with the self-complementarity of the DNA, minimizing interfering reactions. DMSO in a PCR

588-543: Is an ingredient in some products listed by the U.S. FDA as fake cancer cures and the FDA has had a running battle with distributors. One such distributor is Mildred Miller, who promoted DMSO for a variety of disorders and was consequently convicted of Medicare fraud . The use of DMSO as an alternative treatment for cancer is of particular concern, as it has been shown to interfere with a variety of chemotherapy drugs, including cisplatin , carboplatin , and oxaliplatin . There

630-453: Is applicable for supercoiled plasmids (to relax before amplification) or DNA templates with high GC-content (to decrease thermostability ). For example, 10% final concentration of DMSO in the PCR mixture with Phusion decreases primer annealing temperature (i.e. primer melting temperature) by 5.5–6.0 °C (9.9–10.8 °F). It is well known as a reversible cell cycle arrester at phase G1 of human lymphoid cells. DMSO may also be used as

672-725: Is frequently used as a solvent for chemical reactions involving salts, most notably Finkelstein reactions and other nucleophilic substitutions . It is also extensively used as an extractant in biochemistry and cell biology. Because DMSO is only weakly acidic, it tolerates relatively strong bases and as such has been extensively used in the study of carbanions . A set of non-aqueous pKa values (C-H, O-H, S-H and N-H acidities) for thousands of organic compounds have been determined in DMSO solution. Because of its high boiling point, 189 °C (372 °F), DMSO evaporates slowly at normal atmospheric pressure. Samples dissolved in DMSO cannot as easily be recovered compared to other solvents, as it

714-416: Is insufficient evidence to support the hypothesis that DMSO has any effect, and most sources agree that its history of side effects when tested warrants caution when using it as a dietary supplement, for which it is marketed heavily with the usual disclaimer . DMSO is commonly used in veterinary medicine as a liniment for horses , alone or in combination with other ingredients. In the latter case, often,

756-465: Is listed as a Schedule 4 (S4) Drug, and a company has been prosecuted for adding it to products as a preservative. Early clinical trials with DMSO were stopped because of questions about its safety, especially its ability to harm the eye. The most commonly reported side effects include headaches and burning and itching on contact with the skin. Strong allergic reactions have been reported. On September 9, 1965, The Wall Street Journal reported that

798-452: Is metabolized by disproportionation to dimethyl sulfide and dimethyl sulfone . It is subject to renal and pulmonary excretion. A possible side effect of DMSO is therefore elevated blood dimethyl sulfide, which may cause a blood borne halitosis symptom. DMSO is marketed as an alternative medicine . Its popularity as an alternative cure is stated to stem from a 60 Minutes documentary in 1980 featuring an early proponent. However, DMSO

840-491: Is sometimes used by humans, though, anecdotally, its benefits in humans may be because the smell of menthol releases serotonin , or due to a placebo effect . Earl Sloan was a US entrepreneur who made his initial fortune selling his father's horse liniment formula beginning in the period following the Civil War. Sloan's liniment with capsicum as a key ingredient was also marketed for human use. He later sold his company to

882-435: Is the complex dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) (RuCl 2 (dmso) 4 ). In this complex, three DMSO ligands are bonded to ruthenium through sulfur. The fourth DMSO is bonded through oxygen. In general, the oxygen-bonded mode is more common. In carbon tetrachloride solutions DMSO functions as a Lewis base with a variety of Lewis acids such as I 2 , phenols , trimethyltin chloride , metalloporphyrins, and

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924-450: Is used as a vehicle in in vivo studies of test compounds. It has, for example, been employed as a co-solvent to assist absorption of the flavonol glycoside Icariin in the nematode worm Caenorhabditis elegans . As with its use in in vitro studies, DMSO has some limitations in animal models . Pleiotropic effects can occur and, if DMSO control groups are not carefully planned, then solvent effects can falsely be attributed to

966-478: Is used in embolization , the therapeutic occlusion of blood vessels. In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. Without it, up to 90% of frozen cells will become inactive. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cells , which are often frozen in

1008-497: Is very difficult to remove all traces of DMSO by conventional rotary evaporation . One technique to fully recover samples is removal of the organic solvent by evaporation followed by addition of water (to dissolve DMSO) and cryodesiccation to remove both DMSO and water. Reactions conducted in DMSO are often diluted with water to precipitate or phase-separate products. The relatively high freezing point of DMSO, 18.5 °C (65.3 °F), means that at, or just below, room temperature it

1050-504: The H-NMR spectrum. It is often mixed with CDCl 3 or CD 2 Cl 2 for lower viscosity and melting points. DMSO is used to dissolve test compounds in in vitro drug discovery and drug design screening programs, including high-throughput screening programs. This is because it is able to dissolve both polar and nonpolar compounds, can be used to maintain stock solutions of test compounds (important when working with

1092-431: The skin , substances dissolved in DMSO may quickly be absorbed. Glove selection is important when working with DMSO. Butyl rubber , fluoroelastomer , neoprene , or thick (15   mil / 0.4   mm ) latex gloves are recommended. Nitrile gloves, which are very commonly used in chemical laboratories, may protect from brief contact but have been found to degrade rapidly with exposure to DMSO. In Australia, it

1134-601: The US FDA approved DMSO for treating interstitial cystitis . In 1980, the US Congress held hearings on claims that the FDA was slow in approving DMSO for other medical uses. In 2007, the US FDA granted "fast track" designation on clinical studies of DMSO's use in reducing brain tissue swelling following traumatic brain injury . DMSO exposure to developing mouse brains can produce brain degeneration. This neurotoxicity could be detected at doses as low as 0.3   mL/kg,

1176-448: The addition of EDTA . It is frequently compounded with antifungal medications, enabling them to penetrate not just skin but also toenails and fingernails. DMSO has been examined for the treatment of numerous conditions and ailments, but the U.S. Food and Drug Administration (FDA) has approved its use only for the symptomatic relief of patients with interstitial cystitis . A 1978 study concluded that DMSO brought significant relief to

1218-473: The dimer Rh 2 Cl 2 (CO) 4 . The donor properties are discussed in the ECW model . The relative donor strength of DMSO toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots . DMSO is a polar aprotic solvent and is less toxic than other members of this class, such as dimethylformamide , dimethylacetamide , N -methyl-2-pyrrolidone , and hexamethylphosphoramide (HMPA). DMSO

1260-625: The intended function of the DMSO is as a solvent, to carry the other ingredients across the skin. Also in horses, DMSO is used intravenously, again alone or in combination with other drugs. It is used alone for the treatment of increased intracranial pressure and/or cerebral edema in horses. The perceived garlic taste upon skin contact with DMSO may be due to nonolfactory activation of TRPA1 receptors in trigeminal ganglia . Unlike dimethyl and diallyl disulfides (which have odors resembling garlic), mono- and tri- sulfides (which typically have foul odors), and similar odiferous sulfur compounds,

1302-556: The legs; or applied in a diluted form, usually added to a bucket of water and sponged on the body. They are used in hot weather to help cool down a horse after working, the alcohol cooling through rapid evaporation, and counterirritant oils dilating capillaries in the skin, increasing the amount of blood releasing heat from the body. Many horse liniment formulas in diluted form have been used on humans, though products for horses which contain DMSO are not suitable for human use, as DMSO carries

Hamlin's Wizard Oil - Misplaced Pages Continue

1344-470: The majority of the 213 patients with inflammatory genitourinary disorders that were studied. The authors recommended DMSO for genitourinary inflammatory conditions not caused by infection or tumor in which symptoms were severe or patients failed to respond to conventional therapy. In interventional radiology , DMSO is used as a solvent for ethylene vinyl alcohol in the Onyx liquid embolic agent, which

1386-449: The predecessor of Warner–Lambert , which was purchased in 2000 by Pfizer . DMSO Dimethyl sulfoxide ( DMSO ) is an organosulfur compound with the formula ( CH 3 ) 2 S O . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has

1428-447: The profits of Hamlin's Wizard Oil to found and manage Chicago's Grand Opera House . In 1916, Lysander's son Lawrence B. Hamlin of Elgin , by then manager of the firm, was fined $ 200 under the 1906 Pure Food and Drug Act for advertising that Hamlin's Wizard Oil could "check the growth and permanently kill cancer." Liniment Liniment (from Latin : linere , meaning "to anoint "), also called embrocation and heat rub ,

1470-488: The prospective drug. For example, even a very low dose of DMSO has a powerful protective effect against paracetamol (acetaminophen)-induced liver injury in mice. DMSO is finding increased use in manufacturing processes to produce microelectronic devices. It is widely used to strip photoresist in TFT-LCD 'flat panel' displays and advanced packaging applications (such as wafer-level packaging / solder bump patterning). DMSO

1512-532: The pure chemical DMSO is odorless. DMSO is a non-toxic solvent with a median lethal dose higher than ethanol (DMSO: LD 50 , oral, rat, 14,500 mg/kg; ethanol: LD 50 , oral, rat, 7,060 mg/kg ). DMSO can cause contaminants, toxins, and medicines to be absorbed through the skin, which may cause unexpected effects. DMSO is thought to increase the effects of blood thinners, steroids, heart medicines, sedatives, and other drugs. In some cases this could be harmful or dangerous. Because DMSO easily penetrates

1554-455: The resultant carbanion is provided by the S(O)R group. The sodium derivative of DMSO formed in this way is referred to as dimsyl sodium . It is a base, e.g., for the deprotonation of ketones to form sodium enolates , phosphonium salts to form Wittig reagents , and formamidinium salts to form diaminocarbenes . It is also a potent nucleophile. In organic synthesis , DMSO is used as

1596-481: The skin and other membranes without damaging them and could carry other compounds into a biological system. In medicine, DMSO is predominantly used as a topical analgesic , a vehicle for topical application of pharmaceuticals, as an anti-inflammatory , and an antioxidant . Because DMSO increases the rate of absorption of some compounds through biological tissues , including skin , it is used in some transdermal drug delivery systems. Its effect may be enhanced with

1638-432: The topical product into the bloodstream. Horse liniment ingredients such as menthol, chloroxylenol , or iodine are also used in different formulas in products used by humans. Absorbine , a horse liniment product manufactured by W.F. Young, Inc. , was reformulated for humans and marketed as Absorbine Jr. The company also acquired other liniment brands including Bigeloil and RefreshMint. The equine version of Absorbine

1680-522: The writings of Robert Jones Burdette . Grinnell College research points out that the Hamlins claimed efficacy for Wizard Oil on not only human beings but also horses and cattle, one poster displaying an elephant drinking the product by lifting the bottle with its trunk. Bottles came in 35¢ and 75¢ sizes. Carl Sandburg inserted two versions of lyrics titled "Wizard Oil" together with a tune into his American Songbag (1927). John Austin Hamlin would use

1722-598: Was first synthesized in 1866 by the Russian scientist Alexander Zaytsev , who reported his findings in 1867. Its modern use as an industrial solvent began through popularization by Thor Smedslund at the Stepan Chemical Company. Dimethyl sulfoxide is produced industrially from dimethyl sulfide , a by-product of the Kraft process , by oxidation with oxygen or nitrogen dioxide . The sulfur center in DMSO

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1764-690: Was said to be usable both internally and topically. Traveling performance troupes advertised the product in medicine shows across the Midwest, with runs as long as six weeks in a town. They used horse-drawn wagons and dressed in silk top hats, frock coats , pinstriped trousers, and patent leather shoes—with spats . They distributed song books at the shows and in pharmacies . Performers included James Whitcomb Riley , singer and composer Paul Dresser from Indiana, and southern gospel music progenitor Charles Davis Tillman . At these gatherings John Austin Hamlin delivered lectures replete with humor borrowed from

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