47:
456:
301:
1395:
73:
1526:
844:
840:
1537:
34:
57:
982:
1951:, alone or in combination with other ingredients. In the latter case, often, 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.
845:
3816:
1457:
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 is a solid, which can limit its utility in some
2182:
DMSO can decompose at the boiling temperature of 189 °C at normal pressure, possibly leading to an explosion. The decomposition is catalyzed by acids and bases and therefore can be relevant at even lower temperatures. A strong to explosive reaction also takes place in combination with halogen
1907:
documentary in 1980 featuring an early proponent. However, DMSO 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
2015:
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.
1653:
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 is an effective
2081:
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.
843:
1448:
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 is very difficult to remove all traces of DMSO by conventional
2295:
Matthews WS, Bares JE, Bartmess JE, Bordwell FG, Cornforth FJ, Drucker GE, Margolin Z, McCallum RJ, McCollum GJ, Vanier NR (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution".
2417:
von
Demselben (1867). "Ueber die Einwirkung von Saltpetersäure auf Schwefelmethyl und Schwefeläthyl" [On the effect of nitric acid on methyl sulfide and ethyl sulfide]. In Erlenmeyer, E.; Rieckher, T.; Volhard, J.; Liebig, J.; Wöhler, F. (eds.).
1931:. There 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
2104:. 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
2091:
reported that 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.
1711:, 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
1645:
effects can occur and, if DMSO control groups are not carefully planned, then solvent effects can falsely be attributed to the prospective drug. For example, even a very low dose of DMSO has a powerful protective effect against
1800:
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.
3609:
3814:, George Kvakovszky; David Villarrubia II & Scott Stevenson et al., "Process for preparing low malodorous dimethyl sulfoxide", published 2009, assigned to Gaylord Chemical Company LLC
861:
1483:
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
1437:. 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
1108:, 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
3548:
3768:
Glindemann D, Novak J, Witherspoon J (January 2006). "Dimethyl sulfoxide (DMSO) waste residues and municipal waste water odor by dimethyl sulfide (DMS): the North-East WPCP plant of
Philadelphia".
1835:
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
1750:, discovered it could penetrate 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
1701:). 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).
4143:
46:
3383:
1603:, 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
3901:
3670:
2070:
3617:
4136:
846:
2840:
Balakin KV, Savchuk NP, Tetko IV (2006). "In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions".
3541:
1964:
4129:
1885:. 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
771:
2061:
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.
1607:
growth and viability, with low DMSO concentrations sometimes stimulating cell growth, and high DMSO concentrations sometimes inhibiting or killing cells.
3894:
2744:"Bioprospecting for antibacterial drugs: a multidisciplinary perspective on natural product source material, bioassay selection and avoidable pitfalls"
1281:
995:
3080:
1325:
1747:
868:
3887:
1453:. One technique to fully recover samples is removal of the organic solvent by evaporation followed by addition of water (to dissolve DMSO) and
2198:(DMS), the corresponding sulfide, also produced by marine phytoplankton and emitted to the oceanic atmosphere where it is oxidized to DMSO, SO
2151:(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 (
1690:. It is added to the PCR mix before reacting, where it interferes with the self-complementarity of the DNA, minimizing interfering reactions.
1067:
in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a
3391:
3094:
Sawai M, Takase K, Teraoka H, Tsukada K (1990). "Reversible G1 arrest in the cell cycle of human lymphoid cell lines by dimethyl sulfoxide".
505:
3282:
1781:. It is frequently compounded with antifungal medications, enabling them to penetrate not just skin but also toenails and fingernails.
3674:
1915:
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
2963:
Kelava T, Cavar I, Čulo F (Oct 2010). "Influence of small doses of various drug vehicles on acetaminophen-induced liver injury".
3587:
3565:
2998:
Kvakovszky G, McKim AS, Moore J (2007). "A Review of
Microelectronic Manufacturing Applications Using DMSO-Based Chemistries".
990:
3869:
3362:
3209:
3146:
2587:
2358:
1743:
1085:
2713:
4173:
2643:
2611:
Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases".
1987:
sulfides (which typically have foul odors), and similar odiferous sulfur compounds, the pure chemical DMSO is odorless.
3855:
3843:
470:
4415:
1445:
values (C-H, O-H, S-H and N-H acidities) for thousands of organic compounds have been determined in DMSO solution.
1002:
3043:
Chakrabarti R, Schutt CE (August 2001). "The enhancement of PCR amplification by low molecular-weight sulfones".
1813:
854:
364:
3642:
1693:
DMSO in a PCR is applicable for supercoiled plasmids (to relax before amplification) or DNA templates with high
1377:. The relative donor strength of DMSO toward a series of acids, versus other Lewis bases, can be illustrated by
2470:
1285:
1105:
1093:
964:
931:
807:
1223:. For this reason, the basicities of many weakly basic organic compounds have been examined in this solvent.
2674:
2522:
Tidwell TT (1990). "Oxidation of
Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update".
1340:
through sulfur. The fourth DMSO is bonded through oxygen. In general, the oxygen-bonded mode is more common.
101:
56:
3811:
3707:
3688:
Carley W (September 9, 1965). "DMSO may have caused death of woman, makers of 'Wonder' drug warn doctors".
3484:"Transient receptor potential channels encode volatile chemicals sensed by rat trigeminal ganglion neurons"
2323:
2097:
1785:
1723:
1616:
studies of test compounds. It has, for example, been employed as a co-solvent to assist absorption of the
1075:
413:
296:
3000:
1146:
434:
2742:
Cushnie TP, Cushnie B, Echeverría J, Fowsantear W, Thammawat S, Dodgson JL, Law S, Clow SM (June 2020).
1584:
1507:
1480:
1343:
In carbon tetrachloride solutions DMSO functions as a Lewis base with a variety of Lewis acids such as
652:
2374:
Thomas R, Shoemaker CB, Eriks K (1966). "The
Molecular and Crystal Structure of Dimethyl Sulfoxide, (H
2183:
compounds, metal nitrides, metal perchlorates, sodium hydride, periodic acid and fluorinating agents.
238:
50:
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions
4420:
4121:
3455:
1675:
1580:
1576:
1434:
1359:
308:
3407:"Say no to DMSO: dimethylsulfoxide inactivates cisplatin, carboplatin, and other platinum complexes"
3184:
1238:
is provided by the S(O)R group. The sodium derivative of DMSO formed in this way is referred to as
3810:
2877:"Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans"
2100:(NAS) published findings in favor of DMSO in 1972. In 1978, the US FDA approved DMSO for treating
1805:
1793:
1719:
1227:
451:
358:
3721:"Dimethyl sulfoxide (DMSO) produces widespread apoptosis in the developing central nervous system"
3690:
3613:
2244:
2236:
2144:
2087:
1867:
1840:
1832:
1422:
1289:
178:
171:
4060:
3879:
2629:
The plots shown in this paper used older parameters. Improved E&C parameters are listed in
2350:
2124:
2105:
1863:
1629:
1604:
1321:
2419:
2343:
2159:) linkages. Deodorization of DMSO is achieved by removing the odorous impurities it contains.
3954:
3199:
2875:
Cai WJ, Huang JH, Zhang SQ, Wu B, Kapahi P, Zhang XM, Shen ZY (2011). Blagosklonny MV (ed.).
2206:
2101:
1932:
1789:
1500:
1403:
1355:
1022:
943:
20:
3719:
Hanslick JL, Lau K, Noguchi KK, Olney JW, Zorumski CF, Mennerick S, Farber NB (April 2009).
3290:
4090:
4055:
3777:
3673:. Commonwealth of Australia: Department of Health and Ageing. 23 April 2003. Archived from
3495:
3009:
2888:
2391:
1898:
1836:
1784:
DMSO has been examined for the treatment of numerous conditions and ailments, but the U.S.
1731:
1430:
422:
89:
1859:(70% EMEM + 30% fetal bovine serum + antibiotic mixture) is used. As part of an
1704:
It is well known as a reversible cell cycle arrester at phase G1 of human lymphoid cells.
896:
8:
4410:
4085:
2524:
2116:
1984:
687:
258:
137:
3781:
3499:
3013:
2892:
2395:
1617:
455:
300:
218:
147:
4152:
3973:
3838:]. Ecomed Sicherheit (in German). Landsberg/Lech: Verlagsgruppe Hüthig Jehle Rehm.
3745:
3720:
3649:
3518:
3483:
3431:
3406:
3259:
3232:
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3025:
2911:
2876:
2771:
2691:
2001:
1972:
1968:
1874:
1844:
1642:
1450:
1297:
736:
721:
198:
3630:
3058:
2551:
Calligaris M (2004). "Structure and bonding in metal sulfoxide complexes: An update".
4405:
4305:
4100:
4028:
3931:
3851:
3839:
3793:
3750:
3523:
3436:
3334:
3330:
3317:
3264:
3205:
3160:
3152:
3142:
3111:
3107:
3062:
3029:
2980:
2916:
2857:
2817:
2775:
2763:
2593:
2583:
2504:
2466:
2354:
2093:
2073:
Drug, and a company has been prosecuted for adding it to products as a preservative.
1976:
1763:
1755:
1415:
1411:
1407:
1394:
1277:
1060:
916:
890:
3595:
3573:
3405:
Hall MD, Telma KA, Chang KE, Lee TD, Madigan JP, Lloyd JR, et al. (July 2014).
3312:
3233:"Onychomycosis treated with a dilute povidone-iodine/dimethyl sulfoxide preparation"
2796:"Investigation of 3 industry-wide applied storage conditions for compound libraries"
2695:
3936:
3785:
3740:
3732:
3513:
3503:
3426:
3418:
3326:
3254:
3244:
3134:
3103:
3054:
3017:
2972:
2906:
2896:
2849:
2807:
2755:
2683:
2620:
2560:
2533:
2496:
2487:
2458:
2399:
2305:
2223:
2217:
2195:
2152:
2148:
1980:
1882:
1878:
1843:, which are often frozen in a mixture of 10% DMSO, a freezing medium, and 30%
1592:
1253:
1117:
1109:
1026:
937:
792:
782:
671:
617:
533:
3482:
Lübbert M, Kyereme J, Schöbel N, Beltrán L, Wetzel CH, Hatt H (October 21, 2013).
3422:
3358:
72:
4204:
4095:
3968:
3508:
2901:
2709:
2273:
2176:
2172:
2032:
1712:
1698:
1663:
1470:
1459:
1293:
1056:
748:
327:
3914:
3138:
3129:
1398:
Distillation of DMSO requires a partial vacuum to achieve a lower boiling point.
386:
4209:
3946:
3045:
2853:
2759:
2651:
2136:
2058:
2043:
1909:
1828:
1708:
1655:
1638:
1588:
1565:
1492:
1265:
1257:
1231:
1174:
1081:
973:
642:
3736:
2564:
2403:
2111:
DMSO exposure to developing mouse brains can produce brain degeneration. This
4399:
4320:
3949:
3156:
3133:. Methods in Molecular Biology. Vol. 368. Humana Press. pp. 39–57.
2812:
2795:
2597:
2462:
2168:
2112:
1797:
1774:
1727:
1600:
1454:
1261:
1240:
1142:
1113:
1053:
632:
606:
596:
289:
2672:
Bordwell FG (1988). "Equilibrium acidities in dimethyl sulfoxide solution".
1788:(FDA) has approved its use only for the symptomatic relief of patients with
4379:
4325:
4285:
4199:
4186:
4164:
3988:
3978:
3797:
3754:
3527:
3440:
3268:
3164:
3081:"Guidelines for PCR Optimization with Phusion High-Fidelity DNA Polymerase"
3066:
2984:
2920:
2861:
2821:
2794:
Ilouga PE, Winkler D, Kirchhoff C, Schierholz B, Wölcke J (November 2007).
2767:
2028:
1916:
1817:
1659:
1170:
1138:
1134:
787:
777:
707:
3115:
2508:
1762:. Because DMSO increases the rate of absorption of some compounds through
1525:
1280:, DMSO is used as a mild oxidant. It forms the basis of several selective
1104:
Dimethyl sulfoxide was first synthesized in 1866 by the
Russian scientist
867:
4358:
4295:
4270:
4260:
4219:
4105:
4023:
4013:
4008:
3993:
3963:
3338:
3313:"Dimethyl Sulfoxide in Treatment of Inflammatory Genitourinary Disorders"
3249:
2537:
1928:
1924:
1824:
1771:
1759:
1647:
1596:
1569:
880:
3708:
https://www.fda.gov/ForIndustry/ImportProgram/ImportAlerts/ucm162294.htm
2687:
2500:
2309:
1300:
is conceptually similar. These all involve formation of an intermediate
853:
278:
4384:
4335:
4315:
4300:
4229:
4156:
4075:
4018:
4003:
3998:
2435:
2230:
2050:
1903:
1860:
1694:
1687:
1536:
860:
628:
561:
309:
249:
4151:
3789:
3021:
2624:
4349:
4330:
4290:
4280:
4265:
4234:
4194:
4110:
3983:
3923:
2630:
2349:(56th ed.). St. Louis, Missouri: Wolters Kluwer Health. p.
2227:
2167:
Dimethyl sulfoxide can produce an explosive reaction when exposed to
1960:
1959:
The perceived garlic taste upon skin contact with DMSO may be due to
1920:
1886:
1852:
1751:
1683:
1679:
1466:
1438:
1378:
1374:
1337:
1301:
1235:
1089:
1049:
910:
698:
33:
2976:
2743:
2485:
Epstein WW, Sweat FW (March 1967). "Dimethyl
Sulfoxide Oxidations".
972:
Except where otherwise noted, data are given for materials in their
4310:
4275:
4255:
4239:
4070:
4033:
2140:
2036:
1944:
1624:
1572:
1561:
1249:
1064:
826:
347:
269:
2741:
1796:
relief to the majority of the 213 patients with inflammatory
177:
170:
4160:
3910:
2440:
Excuse me sir, would you like to buy a kilo of isopropyl bromide?
1901:. Its popularity as an alternative cure is stated to stem from a
1620:
1612:
1426:
1245:
949:
582:
373:
3909:
2793:
2209:(MSM), a related chemical often marketed as a dietary supplement
1316:
Related to its ability to dissolve many salts, DMSO is a common
1141:
and the oxygen is nucleophilic toward hard electrophiles. With
1351:
1344:
1317:
1178:
1088:
consistent with other three-coordinate S(IV) compounds, with a
1068:
1044:
1041:
1030:
229:
2580:
Lewis basicity and affinity scales : data and measurement
2453:
Roy, Kathrin-Maria (15 June 2000), "Sulfones and
Sulfoxides",
1754:, a vehicle for topical application of pharmaceuticals, as an
3460:
2938:
2582:. Chichester, West Sussex, U.K.: John Wiley. pp. 50–51.
2294:
2156:
2054:
2024:
1948:
1181:
758:
397:
209:
160:
3481:
2139:
can cause odor problems in municipal effluents: waste water
1406:
and is less toxic than other members of this class, such as
439:
4050:
2457:, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA,
2123:
mL/kg, a level exceeded in children exposed to DMSO during
2020:
1856:
1848:
1809:
1778:
1767:
1074:
In terms of chemical structure, the molecule has idealized
338:
3767:
1777:
systems. Its effect may be enhanced with the addition of
1499:
O resonance in the H-NMR spectrum. It is often mixed with
3093:
1442:
1212:
The methyl groups of DMSO are only weakly acidic, with a
1071:-like taste in the mouth after DMSO is absorbed by skin.
3829:
2610:
2096:
using DMSO was halted and did not begin again until the
2023:, substances dissolved in DMSO may quickly be absorbed.
1831:
and is still an important constituent of cryoprotectant
1742:
Use of DMSO in medicine dates from around 1963, when an
1491:
are its high viscosity, which broadens signals, and its
3718:
1847:. In the cryogenic freezing of heteroploid cell lines (
1591:
of test compounds (important when working with a large
1579:
programs. This is because it is able to dissolve both
3874:
3310:
3588:"Material Safety Data Sheet: Ethyl alcohol 200 Proof"
1429:
for chemical reactions involving salts, most notably
1336:). In this complex, three DMSO ligands are bonded to
2997:
2373:
1866:
the DMSO is re-infused along with the patient's own
3671:"Brisbane drug company convicted of counterfeiting"
2839:
2171:; at a low temperature, this reaction produces the
3230:
2342:
1943:DMSO is commonly used in veterinary medicine as a
1052:most widely used commercially. It is an important
3547:. Gaylord Chemical Company, L.L.C. 21 July 2016.
3404:
3311:Shirley SW, Stewart BH, Mirelman S (March 1978).
3042:
1979:disulfides (which have odors resembling garlic),
1855:, etc.) a mixture of 10% DMSO with 90%
1326:dichlorotetrakis(dimethyl sulfoxide)ruthenium(II)
1226:Deprotonation of DMSO requires strong bases like
647:0.556 millibars or 0.0556 kPa at 20 °C
4397:
3566:"Material Safety Data Sheet: Dimethyl Sulfoxide"
3384:"187 Fake Cancer "Cures" Consumers Should Avoid"
2953:
2578:Laurence, Christian; Gal, Jean-François (2010).
1244:. It is a base, e.g., for the deprotonation of
385:
16:Organosulfur chemical compound used as a solvent
2962:
2958:
2956:
2874:
2835:
2833:
2831:
2789:
2787:
2785:
2737:
2735:
2733:
2731:
2027:selection is important when working with DMSO.
1128:
842:
146:
3542:"Safety Data Sheet: Dimethyl Sulfoxide (DMSO)"
3197:
2455:Ullmann's Encyclopedia of Industrial Chemistry
2424:(in German). Meyer ; Winter. p. 148.
1820:, the therapeutic occlusion of blood vessels.
1658:, being safer than many of the others such as
1650:(acetaminophen)-induced liver injury in mice.
4137:
3895:
2416:
3131:Cryopreservation and Freeze-Drying Protocols
2868:
2828:
2782:
2728:
2571:
2484:
1373:. The donor properties are discussed in the
3447:
2936:
2577:
2008:, oral, rat, 14,500 mg/kg; ethanol: LD
1792:. A 1978 study concluded that DMSO brought
1559:DMSO is used to dissolve test compounds in
1099:
19:"DMSO" redirects here. For other uses, see
4144:
4130:
3902:
3888:
3830:Roth, Lutz; Weller, Ursula (August 2000).
3703:
3701:
3237:International Medical Case Reports Journal
2550:
454:
299:
257:
3744:
3517:
3507:
3430:
3258:
3248:
2932:
2930:
2910:
2900:
2811:
2410:
2226:(also DMS), the corresponding sulfate: a
421:
3376:
3352:
3350:
3348:
3231:Capriotti K, Capriotti JA (2015-10-08).
2671:
2274:"Dimethyl Sulfoxide (DMSO) -- Technical"
2214:Related compounds with methyl on oxygen
1718:In cell culture, DMSO is used to induce
1517:for lower viscosity and melting points.
1393:
1311:
3870:International Chemical Safety Card 0459
3698:
2521:
1892:
1816:liquid embolic agent, which is used in
450:
363:
277:
4398:
3687:
3554:from the original on 13 February 2019.
3453:
3356:
3128:
2927:
2710:"Bordwell pKa Table (Acidity in DMSO)"
2434:
2266:
1938:
1744:Oregon Health & Science University
1637:studies, DMSO has some limitations in
611:189 °C (372 °F; 462 K)
290:
4125:
3883:
3875:Dimethyl Sulfoxide Information Center
3363:National Council Against Health Fraud
3345:
2939:"Biological actions of drug solvents"
2340:
1425:(HMPA). DMSO is frequently used as a
1086:trigonal pyramidal molecular geometry
885:89 °C (192 °F; 362 K)
482:Key: IAZDPXIOMUYVGZ-UHFFFAOYSA-N
237:
217:
60:Spacefill model of dimethyl sulfoxide
3770:Environmental Science and Technology
2205:Dimethyl sulfone, commonly known as
1268:. It is also a potent nucleophile.
791:
781:
601:19 °C (66 °F; 292 K)
3602:
2716:from the original on 9 October 2008
2452:
2162:
2019:Because DMSO easily penetrates the
2000:DMSO is a non-toxic solvent with a
1587:compounds, can be used to maintain
1358:, metalloporphyrins, and the dimer
1282:sulfonium-based oxidation reactions
492:Key: IAZDPXIOMUYVGZ-UHFFFAOYAR
376:
346:
13:
2446:
2076:
1495:, which leads to an overwhelming H
1234:. Stabilization of the resultant
838:
55:
45:
14:
4432:
3863:
2800:Journal of Biomolecular Screening
2247:, also known as the "Toxic Woman"
125:Methyl sulfoxide (2:1), Dermasorb
3832:Gefährliche Chemische Reaktionen
3631:Rubber Chemical Resistance Chart
2069:In Australia, it is listed as a
2012:, oral, rat, 7,060 mg/kg).
1808:, DMSO is used as a solvent for
1535:
1524:
1048:. This colorless liquid is the
980:
545:
71:
32:
3823:
3812:US application 2009005601A1
3804:
3761:
3712:
3681:
3663:
3635:
3624:
3580:
3558:
3534:
3475:
3454:Saling, Joseph (20 June 2022).
3398:
3304:
3275:
3224:
3204:. Kluwer Academic. p. 20.
3191:
3122:
3087:
3073:
3036:
2991:
2702:
2665:
2636:
2604:
2544:
2515:
2478:
2442:. Pierce Chemical. p. 145.
2130:
1746:Medical School team, headed by
1384:
976:(at 25 °C , 100 kPa).
479:InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
3357:Jarvis WT (24 November 2001).
2937:Kelava T, Cavar I (Nov 2011).
2553:Coordination Chemistry Reviews
2428:
2367:
2334:
2316:
2288:
2257:
1479:), it is a useful solvent for
1324:. Illustrative is the complex
1116:, by oxidation with oxygen or
965:Dimethyl sulfoxide (data page)
932:Sodium methylsulfinylmethylide
808:Occupational safety and health
554:
551:
539:
489:InChI=1/C2H6OS/c1-4(2)3/h1-2H3
78:A sample of dimethyl sulfoxide
1:
3594:. 21 May 2013. Archived from
3572:. 21 May 2013. Archived from
3423:10.1158/0008-5472.CAN-14-0247
3059:10.1016/S0378-1119(01)00621-7
2675:Accounts of Chemical Research
2613:Journal of Chemical Education
2251:
2064:
2004:higher than ethanol (DMSO: LD
1724:P19 embryonic carcinoma cells
1610:DMSO is used as a vehicle in
1545:DMSO is used as a solvent in
1133:The sulfur center in DMSO is
3913:, including antispasmodics (
3836:Dangerous Chemical Reactions
3509:10.1371/journal.pone.0077998
3331:10.1016/0090-4295(78)90118-8
3201:The century of space science
3108:10.1016/0014-4827(90)90108-m
2902:10.1371/journal.pone.0028835
2192:Varying oxidation of sulfur
2098:National Academy of Sciences
1786:Food and Drug Administration
1308:SX where X is a heteroatom)
1129:Reactions with electrophiles
1123:
7:
3139:10.1007/978-1-59745-362-2_3
2842:Current Medicinal Chemistry
2239:, another methylating agent
2220:, the corresponding sulfite
2186:
1995:
1737:
1707:DMSO may also be used as a
1147:trimethylsulfoxonium iodide
41:
10:
4437:
2854:10.2174/092986706775197917
2760:10.1007/s11095-020-02849-1
2345:Drug Facts and Comparisons
1908:consequently convicted of
1669:
1435:nucleophilic substitutions
1389:
1286:Pfitzner–Moffatt oxidation
1271:
1207:
18:
4367:
4348:
4248:
4218:
4185:
4172:
4042:
3945:
3922:
3737:10.1016/j.nbd.2008.11.006
2565:10.1016/j.ccr.2004.02.005
2404:10.1107/S0365110X66002263
2147:(anoxic) conditions into
1990:
1676:polymerase chain reaction
1577:high-throughput screening
1458:chemical processes (e.g.
970:
963:
958:
902:
805:
800:
764:
714:
526:
501:
466:
130:
120:
106:(Methanesulfinyl)methane
100:
88:
83:
70:
40:
31:
2813:10.1177/1087057106295507
2463:10.1002/14356007.a25_487
2328:pubchem.ncbi.nlm.nih.gov
2276:. Atofina Chemicals, inc
2057:gloves are recommended.
1954:
1868:hematopoietic stem cells
1841:hematopoietic stem cells
1827:DMSO has been used as a
1806:interventional radiology
1441:. A set of non-aqueous
1228:lithium diisopropylamide
1100:Synthesis and production
959:Supplementary data page
94:(Methanesulfinyl)methane
4416:Foul-smelling chemicals
3725:Neurobiology of Disease
3691:The Wall Street Journal
3643:"Chemical hygiene plan"
3614:American Cancer Society
3198:Johannes Geiss (2001).
2965:Can J Physiol Pharmacol
2748:Pharmaceutical Research
2237:Methyl methanesulfonate
2088:The Wall Street Journal
1897:DMSO is marketed as an
1873:DMSO is metabolized by
1423:hexamethylphosphoramide
1090:nonbonded electron pair
4061:Salicylhydroxamic acid
3456:"DMSO: Uses and Risks"
3287:www.accessdata.fda.gov
2341:Novak KM, ed. (2002).
2125:bone marrow transplant
2106:traumatic brain injury
2085:On September 9, 1965,
1864:bone marrow transplant
1810:ethylene vinyl alcohol
1633:. As with its use in
1630:Caenorhabditis elegans
1399:
1322:coordination chemistry
1112:, a by-product of the
849:
111:Dimethyl(oxido)sulfur
61:
51:
3598:on 19 September 2018.
3576:on 19 September 2018.
2943:Periodicum Biologorum
2421:Annalen der Pharmacie
2207:methylsulfonylmethane
2143:transform DMSO under
2115:could be detected at
2102:interstitial cystitis
1790:interstitial cystitis
1770:, it is used in some
1732:skeletal muscle cells
1431:Finkelstein reactions
1419:-methyl-2-pyrrolidone
1404:polar aprotic solvent
1397:
1356:trimethyltin chloride
1312:Ligand and Lewis base
1092:on the approximately
1023:organosulfur compound
848:
123:Methylsulfinylmethane
102:Systematic IUPAC name
59:
49:
21:DMSO (disambiguation)
4091:Pentosan polysulfate
4056:Acetohydroxamic acid
3283:"Import Alert 62-06"
3250:10.2147/IMCRJ.S90775
2538:10.1055/s-1990-27036
2324:"Dimethyl sulfoxide"
1899:alternative medicine
1893:Alternative medicine
1837:embryonic stem cells
1680:secondary structures
1575:programs, including
1059:that dissolves both
831:(fire diamond)
90:Preferred IUPAC name
4086:Magnesium hydroxide
3782:2006EnST...40..202G
3500:2013PLoSO...877998L
3014:2007ECSTr..11b.227K
2893:2011PLoSO...628835C
2688:10.1021/ar00156a004
2501:10.1021/cr60247a001
2436:Gergel, Max G.
2396:1966AcCry..21...12T
2310:10.1021/ja00857a010
2135:DMSO disposed into
1939:Veterinary medicine
1290:Corey–Kim oxidation
742:Trigonal pyramidal
618:Solubility in water
569: g·mol
199:Beilstein Reference
28:
27:Dimethyl sulfoxide
4375:Dimethyl sulfoxide
4081:Dimethyl sulfoxide
3650:Cornell University
2754:(7): Article 125.
2002:median lethal dose
1969:trigeminal ganglia
1875:disproportionation
1845:fetal bovine serum
1764:biological tissues
1618:flavonol glycoside
1601:cell culture media
1451:rotary evaporation
1400:
1298:Kornblum oxidation
1061:polar and nonpolar
1015:Dimethyl sulfoxide
1003:Infobox references
903:Related compounds
850:
577:Colourless liquid
365:Dimethyl+sulfoxide
62:
52:
26:
4393:
4392:
4344:
4343:
4306:Meclofenamic acid
4174:Anti-inflammatory
4119:
4118:
4101:Phenyl salicylate
4043:Other urologicals
4029:Trospium chloride
3932:Ammonium chloride
3790:10.1021/es051312a
3417:(14): 3913–3922.
3211:978-0-7923-7195-3
3148:978-1-58829-377-0
3022:10.1149/1.2779383
2625:10.1021/ed054p612
2589:978-0-470-74957-9
2360:978-1-57439-110-7
2304:(24): 7006–7014.
2263:DMSO (medication)
2094:Clinical research
1919:drugs, including
1756:anti-inflammatory
1678:(PCR) to inhibit
1412:dimethylacetamide
1408:dimethylformamide
1278:organic synthesis
1254:phosphonium salts
1169:This salt can be
1106:Alexander Zaytsev
1063:compounds and is
1011:Chemical compound
1009:
1008:
924:Related compounds
917:Diethyl sulfoxide
891:Safety data sheet
435:CompTox Dashboard
179:Interactive image
172:Interactive image
114:
109:
66:
65:
4428:
4421:Methyl compounds
4183:
4182:
4146:
4139:
4132:
4123:
4122:
3937:Calcium chloride
3904:
3897:
3890:
3881:
3880:
3858:
3849:
3827:
3821:
3820:
3819:
3815:
3808:
3802:
3801:
3765:
3759:
3758:
3748:
3716:
3710:
3705:
3696:
3695:
3694:. New York City.
3685:
3679:
3678:
3667:
3661:
3660:
3658:
3657:
3647:
3639:
3633:
3628:
3622:
3621:
3620:on 27 July 2010.
3616:. Archived from
3606:
3600:
3599:
3584:
3578:
3577:
3562:
3556:
3555:
3553:
3546:
3538:
3532:
3531:
3521:
3511:
3479:
3473:
3472:
3470:
3468:
3451:
3445:
3444:
3434:
3402:
3396:
3395:
3394:on 23 July 2017.
3390:. Archived from
3380:
3374:
3373:
3371:
3369:
3354:
3343:
3342:
3308:
3302:
3301:
3299:
3298:
3289:. Archived from
3279:
3273:
3272:
3262:
3252:
3228:
3222:
3221:
3219:
3218:
3195:
3189:
3188:
3182:
3178:
3176:
3168:
3126:
3120:
3119:
3091:
3085:
3084:
3077:
3071:
3070:
3053:(1–2): 293–298.
3040:
3034:
3033:
3001:ECS Transactions
2995:
2989:
2988:
2960:
2951:
2950:
2934:
2925:
2924:
2914:
2904:
2872:
2866:
2865:
2837:
2826:
2825:
2815:
2791:
2780:
2779:
2739:
2726:
2725:
2723:
2721:
2706:
2700:
2699:
2669:
2663:
2662:
2660:
2659:
2650:. Archived from
2648:exactantigen.com
2640:
2634:
2628:
2608:
2602:
2601:
2575:
2569:
2568:
2559:(3–4): 351–375.
2548:
2542:
2541:
2519:
2513:
2512:
2488:Chemical Reviews
2482:
2476:
2475:
2450:
2444:
2443:
2432:
2426:
2425:
2414:
2408:
2407:
2384:Acta Crystallogr
2371:
2365:
2364:
2348:
2338:
2332:
2331:
2320:
2314:
2313:
2298:J. Am. Chem. Soc
2292:
2286:
2285:
2283:
2281:
2270:
2264:
2261:
2224:Dimethyl sulfate
2218:Dimethyl sulfite
2196:Dimethyl sulfide
2163:Explosion hazard
2149:dimethyl sulfide
2122:
2049:
2042:
1933:usual disclaimer
1883:dimethyl sulfone
1879:dimethyl sulfide
1674:DMSO is used in
1593:chemical library
1539:
1528:
1222:
1200:)O + NaI + H
1188:I + NaH → (CH
1118:nitrogen dioxide
1110:dimethyl sulfide
1047:
993:
987:
984:
983:
944:Dimethyl sulfone
938:Dimethyl sulfide
870:
863:
856:
841:
795:
785:
757:
706:
672:Refractive index
590:
568:
556:
553:
547:
541:
534:Chemical formula
459:
458:
443:
441:
425:
389:
378:
367:
350:
328:Gmelin Reference
311:
303:
292:
281:
261:
241:
221:
181:
174:
150:
112:
107:
75:
42:
36:
29:
25:
4436:
4435:
4431:
4430:
4429:
4427:
4426:
4425:
4396:
4395:
4394:
4389:
4363:
4340:
4244:
4222:
4214:
4205:Oxyphenbutazone
4177:
4175:
4168:
4150:
4120:
4115:
4096:Phenazopyridine
4038:
3969:Desfesoterodine
3955:antimuscarinics
3952:
3941:
3918:
3908:
3866:
3861:
3846:
3828:
3824:
3817:
3809:
3805:
3766:
3762:
3717:
3713:
3706:
3699:
3686:
3682:
3669:
3668:
3664:
3655:
3653:
3645:
3641:
3640:
3636:
3629:
3625:
3608:
3607:
3603:
3586:
3585:
3581:
3564:
3563:
3559:
3551:
3544:
3540:
3539:
3535:
3480:
3476:
3466:
3464:
3452:
3448:
3411:Cancer Research
3403:
3399:
3382:
3381:
3377:
3367:
3365:
3355:
3346:
3309:
3305:
3296:
3294:
3281:
3280:
3276:
3229:
3225:
3216:
3214:
3212:
3196:
3192:
3180:
3179:
3170:
3169:
3149:
3127:
3123:
3092:
3088:
3079:
3078:
3074:
3041:
3037:
2996:
2992:
2977:10.1139/Y10-065
2961:
2954:
2935:
2928:
2873:
2869:
2838:
2829:
2792:
2783:
2740:
2729:
2719:
2717:
2708:
2707:
2703:
2682:(12): 456–463.
2670:
2666:
2657:
2655:
2642:
2641:
2637:
2609:
2605:
2590:
2576:
2572:
2549:
2545:
2532:(10): 857–870.
2520:
2516:
2483:
2479:
2473:
2451:
2447:
2433:
2429:
2415:
2411:
2381:
2377:
2372:
2368:
2361:
2339:
2335:
2322:
2321:
2317:
2293:
2289:
2279:
2277:
2272:
2271:
2267:
2262:
2258:
2254:
2201:
2189:
2177:Swern oxidation
2165:
2133:
2120:
2079:
2077:Clinical safety
2071:Schedule 4 (S4)
2067:
2047:
2040:
2033:fluoroelastomer
2011:
2007:
1998:
1993:
1957:
1941:
1895:
1740:
1720:differentiation
1713:liquid nitrogen
1699:thermostability
1672:
1664:dichloromethane
1599:with water and
1589:stock solutions
1557:
1556:
1555:
1554:
1542:
1541:
1540:
1531:
1530:
1529:
1515:
1511:
1504:
1498:
1490:
1477:
1462:with cooling).
1460:crystallization
1455:cryodesiccation
1392:
1387:
1371:
1367:
1363:
1348:
1335:
1331:
1314:
1307:
1294:Swern oxidation
1274:
1266:diaminocarbenes
1258:Wittig reagents
1248:to form sodium
1220:
1213:
1210:
1203:
1199:
1195:
1191:
1164:
1160:
1156:
1131:
1126:
1102:
1079:
1057:aprotic solvent
1040:
1039:
1034:
1012:
1005:
1000:
999:
998: ?)
989:
985:
981:
977:
954:
925:
913:
875:
874:
873:
872:
865:
858:
851:
847:
839:
818:
774:
755:
751:
739:
737:Molecular shape
730:
724:
704:
691:
686:
682:
680:
661:
620:
588:
566:
550:
544:
536:
522:
519:
514:
509:
508:
497:
494:
493:
490:
484:
483:
480:
474:
473:
462:
444:
437:
428:
408:
392:
379:
353:
330:
321:
284:
264:
244:
224:
201:
184:
164:
153:
140:
126:
124:
116:
115:
110:
96:
95:
79:
76:
24:
17:
12:
11:
5:
4434:
4424:
4423:
4418:
4413:
4408:
4391:
4390:
4388:
4387:
4382:
4377:
4371:
4369:
4365:
4364:
4362:
4361:
4355:
4353:
4346:
4345:
4342:
4341:
4339:
4338:
4333:
4328:
4323:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4252:
4250:
4246:
4245:
4243:
4242:
4237:
4232:
4226:
4224:
4216:
4215:
4213:
4212:
4210:Phenylbutazone
4207:
4202:
4197:
4191:
4189:
4180:
4170:
4169:
4149:
4148:
4141:
4134:
4126:
4117:
4116:
4114:
4113:
4108:
4103:
4098:
4093:
4088:
4083:
4078:
4073:
4064:
4063:
4058:
4046:
4044:
4040:
4039:
4037:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3971:
3966:
3960:
3958:
3950:antispasmodics
3943:
3942:
3940:
3939:
3934:
3928:
3926:
3920:
3919:
3907:
3906:
3899:
3892:
3884:
3878:
3877:
3872:
3865:
3864:External links
3862:
3860:
3859:
3844:
3822:
3803:
3776:(1): 202–207.
3760:
3711:
3697:
3680:
3677:on 2012-03-21.
3662:
3652:. October 1999
3634:
3623:
3601:
3592:ScienceLab.com
3579:
3570:ScienceLab.com
3557:
3533:
3494:(10): e77998.
3474:
3446:
3397:
3375:
3344:
3325:(3): 215–220.
3303:
3274:
3223:
3210:
3190:
3181:|journal=
3147:
3121:
3086:
3072:
3035:
3008:(2): 227–234.
2990:
2971:(10): 980–87.
2952:
2926:
2887:(12): e28835.
2867:
2848:(2): 223–241.
2827:
2781:
2727:
2701:
2664:
2635:
2603:
2588:
2570:
2543:
2514:
2495:(3): 247–260.
2477:
2471:
2445:
2438:(March 1977).
2427:
2409:
2379:
2375:
2366:
2359:
2333:
2315:
2287:
2265:
2255:
2253:
2250:
2249:
2248:
2245:Gloria Ramirez
2242:
2241:
2240:
2234:
2221:
2212:
2211:
2210:
2203:
2199:
2188:
2185:
2169:acyl chlorides
2164:
2161:
2132:
2129:
2078:
2075:
2066:
2063:
2039:, or thick (15
2009:
2005:
1997:
1994:
1992:
1989:
1963:activation of
1956:
1953:
1940:
1937:
1910:Medicare fraud
1894:
1891:
1829:cryoprotectant
1739:
1736:
1728:cardiomyocytes
1709:cryoprotectant
1671:
1668:
1656:paint stripper
1595:), is readily
1566:drug discovery
1544:
1543:
1534:
1533:
1532:
1523:
1522:
1521:
1520:
1519:
1513:
1509:
1502:
1496:
1493:hygroscopicity
1488:
1475:
1391:
1388:
1386:
1383:
1369:
1365:
1361:
1346:
1333:
1329:
1313:
1310:
1305:
1284:including the
1273:
1270:
1264:salts to form
1232:sodium hydride
1218:
1209:
1206:
1205:
1204:
1201:
1197:
1193:
1189:
1175:sodium hydride
1167:
1166:
1162:
1158:
1154:
1130:
1127:
1125:
1122:
1101:
1098:
1077:
1037:
1032:
1010:
1007:
1006:
1001:
979:
978:
974:standard state
971:
968:
967:
961:
960:
956:
955:
953:
952:
947:
941:
935:
928:
926:
923:
920:
919:
914:
908:
905:
904:
900:
899:
894:
887:
886:
883:
877:
876:
866:
859:
852:
837:
836:
835:
834:
832:
823:
822:
819:
816:
813:
812:
803:
802:
798:
797:
775:
770:
767:
766:
762:
761:
752:
747:
744:
743:
740:
735:
732:
731:
728:
725:
720:
717:
716:
712:
711:
710:at 20 °C
701:
695:
694:
689:
683:
678:
670:
667:
666:
663:
659:
649:
648:
645:
643:Vapor pressure
639:
638:
635:
625:
624:
621:
616:
613:
612:
609:
603:
602:
599:
593:
592:
585:
579:
578:
575:
571:
570:
564:
558:
557:
548:
542:
537:
532:
529:
528:
524:
523:
521:
520:
517:
515:
512:
504:
503:
502:
499:
498:
496:
495:
491:
488:
487:
485:
481:
478:
477:
469:
468:
467:
464:
463:
461:
460:
447:
445:
433:
430:
429:
427:
426:
418:
416:
410:
409:
407:
406:
402:
400:
394:
393:
391:
390:
382:
380:
372:
369:
368:
361:
355:
354:
352:
351:
343:
341:
335:
334:
331:
326:
323:
322:
320:
319:
315:
313:
305:
304:
294:
286:
285:
283:
282:
274:
272:
266:
265:
263:
262:
254:
252:
246:
245:
243:
242:
234:
232:
226:
225:
223:
222:
214:
212:
206:
205:
202:
197:
194:
193:
190:
189:Abbreviations
186:
185:
183:
182:
175:
167:
165:
158:
155:
154:
152:
151:
143:
141:
136:
133:
132:
128:
127:
122:
118:
117:
108:(substitutive)
105:
104:
98:
97:
93:
92:
86:
85:
81:
80:
77:
68:
67:
64:
63:
53:
38:
37:
15:
9:
6:
4:
3:
2:
4433:
4422:
4419:
4417:
4414:
4412:
4409:
4407:
4404:
4403:
4401:
4386:
4383:
4381:
4378:
4376:
4373:
4372:
4370:
4366:
4360:
4357:
4356:
4354:
4351:
4347:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4321:Niflumic acid
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4254:
4253:
4251:
4247:
4241:
4238:
4236:
4233:
4231:
4228:
4227:
4225:
4221:
4217:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4192:
4190:
4188:
4187:Pyrazolidines
4184:
4181:
4179:
4176:preparations,
4171:
4166:
4162:
4161:muscular pain
4158:
4155:products for
4154:
4147:
4142:
4140:
4135:
4133:
4128:
4127:
4124:
4112:
4109:
4107:
4104:
4102:
4099:
4097:
4094:
4092:
4089:
4087:
4084:
4082:
4079:
4077:
4074:
4072:
4069:
4066:
4065:
4062:
4059:
4057:
4054:
4052:
4048:
4047:
4045:
4041:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3961:
3959:
3956:
3951:
3948:
3944:
3938:
3935:
3933:
3930:
3929:
3927:
3925:
3921:
3916:
3912:
3905:
3900:
3898:
3893:
3891:
3886:
3885:
3882:
3876:
3873:
3871:
3868:
3867:
3857:
3856:3-609-48040-8
3853:
3847:
3845:3-609-73090-0
3841:
3837:
3833:
3826:
3813:
3807:
3799:
3795:
3791:
3787:
3783:
3779:
3775:
3771:
3764:
3756:
3752:
3747:
3742:
3738:
3734:
3730:
3726:
3722:
3715:
3709:
3704:
3702:
3693:
3692:
3684:
3676:
3672:
3666:
3651:
3644:
3638:
3632:
3627:
3619:
3615:
3611:
3605:
3597:
3593:
3589:
3583:
3575:
3571:
3567:
3561:
3550:
3543:
3537:
3529:
3525:
3520:
3515:
3510:
3505:
3501:
3497:
3493:
3489:
3485:
3478:
3463:
3462:
3457:
3450:
3442:
3438:
3433:
3428:
3424:
3420:
3416:
3412:
3408:
3401:
3393:
3389:
3385:
3379:
3364:
3360:
3353:
3351:
3349:
3340:
3336:
3332:
3328:
3324:
3320:
3319:
3314:
3307:
3293:on 2017-02-04
3292:
3288:
3284:
3278:
3270:
3266:
3261:
3256:
3251:
3246:
3242:
3238:
3234:
3227:
3213:
3207:
3203:
3202:
3194:
3186:
3174:
3166:
3162:
3158:
3154:
3150:
3144:
3140:
3136:
3132:
3125:
3117:
3113:
3109:
3105:
3101:
3097:
3096:Exp. Cell Res
3090:
3082:
3076:
3068:
3064:
3060:
3056:
3052:
3048:
3047:
3039:
3031:
3027:
3023:
3019:
3015:
3011:
3007:
3003:
3002:
2994:
2986:
2982:
2978:
2974:
2970:
2966:
2959:
2957:
2949:(3): 311–320.
2948:
2944:
2940:
2933:
2931:
2922:
2918:
2913:
2908:
2903:
2898:
2894:
2890:
2886:
2882:
2878:
2871:
2863:
2859:
2855:
2851:
2847:
2843:
2836:
2834:
2832:
2823:
2819:
2814:
2809:
2805:
2801:
2797:
2790:
2788:
2786:
2777:
2773:
2769:
2765:
2761:
2757:
2753:
2749:
2745:
2738:
2736:
2734:
2732:
2715:
2711:
2705:
2697:
2693:
2689:
2685:
2681:
2677:
2676:
2668:
2654:on 2009-10-05
2653:
2649:
2645:
2639:
2632:
2626:
2622:
2618:
2614:
2607:
2599:
2595:
2591:
2585:
2581:
2574:
2566:
2562:
2558:
2554:
2547:
2539:
2535:
2531:
2527:
2526:
2518:
2510:
2506:
2502:
2498:
2494:
2490:
2489:
2481:
2474:
2468:
2464:
2460:
2456:
2449:
2441:
2437:
2431:
2423:
2422:
2413:
2405:
2401:
2397:
2393:
2389:
2385:
2370:
2362:
2356:
2352:
2347:
2346:
2337:
2329:
2325:
2319:
2311:
2307:
2303:
2299:
2291:
2275:
2269:
2260:
2256:
2246:
2243:
2238:
2235:
2232:
2229:
2225:
2222:
2219:
2216:
2215:
2213:
2208:
2204:
2197:
2194:
2193:
2191:
2190:
2184:
2180:
2178:
2174:
2170:
2160:
2158:
2155:) and C-S-H (
2154:
2150:
2146:
2142:
2138:
2128:
2126:
2119:as low as 0.3
2118:
2114:
2113:neurotoxicity
2109:
2107:
2103:
2099:
2095:
2090:
2089:
2083:
2074:
2072:
2062:
2060:
2056:
2052:
2045:
2038:
2034:
2030:
2026:
2022:
2017:
2013:
2003:
1988:
1986:
1982:
1978:
1974:
1970:
1967:receptors in
1966:
1962:
1952:
1950:
1946:
1936:
1934:
1930:
1926:
1922:
1918:
1913:
1911:
1906:
1905:
1900:
1890:
1888:
1884:
1880:
1876:
1871:
1869:
1865:
1862:
1858:
1854:
1850:
1846:
1842:
1838:
1834:
1833:vitrification
1830:
1826:
1821:
1819:
1815:
1811:
1807:
1802:
1799:
1798:genitourinary
1795:
1791:
1787:
1782:
1780:
1776:
1775:drug delivery
1773:
1769:
1765:
1761:
1757:
1753:
1749:
1748:Stanley Jacob
1745:
1735:
1733:
1729:
1725:
1721:
1716:
1714:
1710:
1705:
1702:
1700:
1697:(to decrease
1696:
1691:
1689:
1685:
1681:
1677:
1667:
1665:
1661:
1657:
1651:
1649:
1644:
1640:
1639:animal models
1636:
1632:
1631:
1626:
1622:
1619:
1615:
1614:
1608:
1606:
1602:
1598:
1594:
1590:
1586:
1582:
1578:
1574:
1571:
1567:
1564:
1563:
1553:drug testing.
1552:
1548:
1538:
1527:
1518:
1516:
1505:
1494:
1487:
1482:
1478:
1474:
1468:
1463:
1461:
1456:
1452:
1446:
1444:
1440:
1436:
1432:
1428:
1424:
1420:
1418:
1413:
1409:
1405:
1396:
1382:
1380:
1376:
1372:
1357:
1353:
1349:
1341:
1339:
1327:
1323:
1319:
1309:
1303:
1299:
1295:
1291:
1287:
1283:
1279:
1269:
1267:
1263:
1262:formamidinium
1259:
1255:
1251:
1247:
1243:
1242:
1241:dimsyl sodium
1237:
1233:
1229:
1224:
1217:
1187:
1186:
1185:
1183:
1180:
1176:
1172:
1152:
1151:
1150:
1148:
1144:
1143:methyl iodide
1140:
1139:electrophiles
1136:
1121:
1119:
1115:
1114:Kraft process
1111:
1107:
1097:
1096:sulfur atom.
1095:
1091:
1087:
1083:
1080:
1072:
1070:
1066:
1062:
1058:
1055:
1051:
1046:
1043:
1035:
1028:
1024:
1020:
1016:
1004:
997:
992:
975:
969:
966:
962:
957:
951:
948:
945:
942:
939:
936:
933:
930:
929:
927:
922:
921:
918:
915:
912:
907:
906:
901:
898:
895:
892:
889:
888:
884:
882:
879:
878:
871:
864:
857:
833:
830:
829:
825:
824:
820:
815:
814:
810:
809:
804:
799:
794:
789:
784:
779:
776:
773:
769:
768:
765:Pharmacology
763:
760:
753:
750:
749:Dipole moment
746:
745:
741:
738:
734:
733:
726:
723:
719:
718:
713:
709:
702:
700:
697:
696:
692:
684:
677:
673:
669:
668:
664:
658:
654:
651:
650:
646:
644:
641:
640:
636:
634:
633:Diethyl ether
630:
627:
626:
622:
619:
615:
614:
610:
608:
607:Boiling point
605:
604:
600:
598:
597:Melting point
595:
594:
586:
584:
581:
580:
576:
573:
572:
565:
563:
560:
559:
538:
535:
531:
530:
525:
516:
511:
510:
507:
500:
486:
476:
475:
472:
465:
457:
453:
452:DTXSID2021735
449:
448:
446:
436:
432:
431:
424:
420:
419:
417:
415:
412:
411:
404:
403:
401:
399:
396:
395:
388:
384:
383:
381:
375:
371:
370:
366:
362:
360:
357:
356:
349:
345:
344:
342:
340:
337:
336:
332:
329:
325:
324:
317:
316:
314:
312:
307:
306:
302:
298:
295:
293:
291:ECHA InfoCard
288:
287:
280:
276:
275:
273:
271:
268:
267:
260:
256:
255:
253:
251:
248:
247:
240:
236:
235:
233:
231:
228:
227:
220:
216:
215:
213:
211:
208:
207:
203:
200:
196:
195:
191:
188:
187:
180:
176:
173:
169:
168:
166:
162:
157:
156:
149:
145:
144:
142:
139:
135:
134:
129:
119:
103:
99:
91:
87:
82:
74:
69:
58:
54:
48:
44:
43:
39:
35:
30:
22:
4380:Idrocilamide
4374:
4326:Piketoprofen
4286:Flurbiprofen
4200:Mofebutazone
4178:non-steroids
4080:
4067:
4049:
3989:Imidafenacin
3979:Fesoterodine
3835:
3831:
3825:
3806:
3773:
3769:
3763:
3728:
3724:
3714:
3689:
3683:
3675:the original
3665:
3654:. Retrieved
3637:
3626:
3618:the original
3604:
3596:the original
3591:
3582:
3574:the original
3569:
3560:
3536:
3491:
3487:
3477:
3465:. Retrieved
3459:
3449:
3414:
3410:
3400:
3392:the original
3387:
3378:
3366:. Retrieved
3322:
3316:
3306:
3295:. Retrieved
3291:the original
3286:
3277:
3240:
3236:
3226:
3215:. Retrieved
3200:
3193:
3130:
3124:
3099:
3095:
3089:
3075:
3050:
3044:
3038:
3005:
2999:
2993:
2968:
2964:
2946:
2942:
2884:
2880:
2870:
2845:
2841:
2806:(1): 21–32.
2803:
2799:
2751:
2747:
2718:. Retrieved
2704:
2679:
2673:
2667:
2656:. Retrieved
2652:the original
2647:
2638:
2616:
2612:
2606:
2579:
2573:
2556:
2552:
2546:
2529:
2523:
2517:
2492:
2486:
2480:
2454:
2448:
2439:
2430:
2420:
2412:
2390:(1): 12–20.
2387:
2383:
2369:
2344:
2336:
2327:
2318:
2301:
2297:
2290:
2278:. Retrieved
2268:
2259:
2181:
2166:
2134:
2131:Odor problem
2110:
2086:
2084:
2080:
2068:
2029:Butyl rubber
2018:
2014:
1999:
1961:nonolfactory
1958:
1942:
1917:chemotherapy
1914:
1902:
1896:
1872:
1822:
1818:embolization
1803:
1783:
1766:, including
1741:
1717:
1706:
1703:
1692:
1684:DNA template
1673:
1660:nitromethane
1652:
1634:
1628:
1611:
1609:
1560:
1558:
1550:
1546:
1485:
1472:
1464:
1447:
1416:
1401:
1385:Applications
1342:
1315:
1275:
1239:
1225:
1215:
1211:
1177:to form the
1171:deprotonated
1168:
1137:toward soft
1135:nucleophilic
1132:
1103:
1073:
1018:
1014:
1013:
827:
817:Main hazards
806:
675:
656:
637:Not soluble
398:RTECS number
192:DMSO, Me2SO
131:Identifiers
121:Other names
4359:Zucapsaicin
4352:derivatives
4296:Indometacin
4271:Etofenamate
4261:Benzydamine
4223:derivatives
4220:Acetic acid
4106:Succinimide
4024:Tolterodine
4014:Solifenacin
4009:Propiverine
3994:Meladrazine
3964:Darifenacin
3953:(primarily
3911:Urologicals
3731:(1): 1–10.
3243:: 231–233.
3102:(1): 4–10.
2619:: 612–613.
2202:and sulfate
1929:oxaliplatin
1925:carboplatin
1825:cryobiology
1794:significant
1772:transdermal
1760:antioxidant
1688:DNA primers
1648:paracetamol
1643:Pleiotropic
1570:drug design
1094:tetrahedral
1084:. It has a
897:Oxford MSDS
881:Flash point
811:(OHS/OSH):
722:Point group
574:Appearance
527:Properties
297:100.000.604
219:CHEBI:28262
4411:Sulfoxides
4400:Categories
4385:Tolazoline
4336:Suxibuzone
4316:Nifenazone
4301:Ketoprofen
4230:Diclofenac
4076:Dapoxetine
4053:analogues:
4019:Terodiline
4004:Oxybutynin
3999:Mirabegron
3974:Emepronium
3924:Acidifiers
3656:2010-04-12
3297:2017-03-05
3217:2011-08-07
2658:2009-10-02
2472:3527306730
2252:References
2231:alkylating
2065:Regulation
1971:. Unlike
1904:60 Minutes
1861:autologous
1695:GC-content
1467:deuterated
1439:carbanions
1433:and other
1402:DMSO is a
1304:species (R
911:sulfoxides
715:Structure
629:Solubility
562:Molar mass
423:YOW8V9698H
250:ChemSpider
159:3D model (
138:CAS Number
113:(additive)
4350:Capsaicin
4331:Piroxicam
4291:Ibuprofen
4281:Feprazone
4266:Bufexamac
4235:Fentiazac
4195:Clofezone
4111:Tiopronin
3984:Flavoxate
3183:ignored (
3173:cite book
3157:1064-3745
3030:137979405
2776:219590658
2631:ECW model
2598:428031803
2525:Synthesis
2228:mutagenic
2157:mercaptan
1921:cisplatin
1889:symptom.
1887:halitosis
1758:, and an
1752:analgesic
1605:cell line
1573:screening
1379:C-B plots
1375:ECW model
1338:ruthenium
1302:sulfonium
1236:carbanion
1161:SO + CH
1145:it forms
1124:Reactions
1050:sulfoxide
1025:with the
821:Irritant
699:Viscosity
623:Miscible
405:PV6210000
318:200-664-3
310:EC Number
239:ChEMBL504
4406:Solvents
4311:Naproxen
4276:Felbinac
4256:Bendazac
4240:Tolmetin
4071:Collagen
4034:Vibegron
3850:CD-ROM:
3798:16433352
3755:19100327
3549:Archived
3528:24205061
3488:PLOS ONE
3441:24812268
3269:26491374
3165:18080461
3067:11675022
2985:20962895
2921:22216122
2881:PLOS ONE
2862:16472214
2822:17099243
2768:32529587
2720:23 April
2714:Archived
2696:26624076
2233:compound
2187:See also
2141:bacteria
2037:neoprene
1996:Toxicity
1973:dimethyl
1945:liniment
1738:Medicine
1715:safely.
1635:in vitro
1625:nematode
1597:miscible
1585:nonpolar
1562:in vitro
1547:in vitro
1292:and the
1256:to form
1250:enolates
1082:symmetry
1065:miscible
1021:) is an
909:Related
828:NFPA 704
801:Hazards
772:ATC code
270:DrugBank
4153:Topical
3947:Urinary
3778:Bibcode
3746:2682536
3519:3804614
3496:Bibcode
3467:19 July
3432:4153432
3368:19 July
3318:Urology
3260:4599634
3116:2298260
3010:Bibcode
2912:3244416
2889:Bibcode
2509:6042131
2392:Bibcode
2173:oxidant
2153:sulfide
2145:hypoxic
2059:Nitrile
1977:diallyl
1812:in the
1686:or the
1682:in the
1670:Biology
1623:in the
1621:Icariin
1613:in vivo
1551:in vivo
1465:In its
1427:solvent
1390:Solvent
1352:phenols
1272:Oxidant
1246:ketones
1208:Acidity
1165:I → I
1027:formula
996:what is
994: (
950:Acetone
790: (
788:M02AX03
786:)
780: (
778:G04BX13
653:Acidity
583:Density
518:CS(C)=O
513:CS(=O)C
374:PubChem
279:DB01093
204:506008
148:67-68-5
4068:Other:
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2280:26 May
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1991:Safety
1949:horses
1927:, and
1469:form (
1421:, and
1332:(dmso)
1318:ligand
1296:. The
1260:, and
1179:sulfur
1069:garlic
991:verify
988:
893:(SDS)
756:
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589:
587:1.1004
506:SMILES
348:D01043
230:ChEMBL
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4368:Other
4249:Other
4157:joint
3834:[
3646:(PDF)
3552:(PDF)
3545:(PDF)
3461:WebMD
3026:S2CID
2772:S2CID
2692:S2CID
2382:SO".
2117:doses
2055:latex
2046:/ 0.4
2025:Glove
1981:mono-
1965:TRPA1
1955:Taste
1726:into
1627:worm
1581:polar
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1471:DMSO-
1328:(RuCl
1182:ylide
1173:with
1149:, I:
1054:polar
703:1.996
693:= 48
685:1.479
591:g⋅cm
567:78.13
471:InChI
333:1556
210:ChEBI
161:JSmol
4159:and
4051:Urea
3915:G04B
3852:ISBN
3840:ISBN
3794:PMID
3751:PMID
3524:PMID
3469:2022
3437:PMID
3370:2022
3335:PMID
3265:PMID
3206:ISBN
3185:help
3161:PMID
3153:ISSN
3143:ISBN
3112:PMID
3063:PMID
3046:Gene
2981:PMID
2917:PMID
2858:PMID
2818:PMID
2764:PMID
2722:2019
2594:OCLC
2584:ISBN
2530:1990
2505:PMID
2467:ISBN
2355:ISBN
2351:2345
2282:2007
2175:for
2021:skin
1985:tri-
1983:and
1975:and
1947:for
1881:and
1857:EMEM
1853:VERO
1849:MDCK
1839:and
1814:Onyx
1779:EDTA
1768:skin
1730:and
1662:and
1583:and
1568:and
1549:and
1501:CDCl
1368:(CO)
1230:and
1221:= 35
1196:S(CH
1019:DMSO
754:3.96
414:UNII
359:MeSH
339:KEGG
4165:M02
3786:doi
3741:PMC
3733:doi
3514:PMC
3504:doi
3427:PMC
3419:doi
3388:FDA
3327:doi
3255:PMC
3245:doi
3135:doi
3104:doi
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