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2D Structure
Also known as: Dmso, 67-68-5, Methyl sulfoxide, Methylsulfinylmethane, Dimethylsulfoxide, Dimethyl sulphoxide
Molecular Formula
C2H6OS
Molecular Weight
78.14  g/mol
InChI Key
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
FDA UNII
YOW8V9698H

A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methylsulfinylmethane
2.1.2 InChI
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
2.1.3 InChI Key
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CS(=O)C
2.2 Other Identifiers
2.2.1 UNII
YOW8V9698H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dimethyl Sulphoxide

2. Dimethylsulfoxide

3. Dimethylsulphinyl

4. Dimethylsulphoxide

5. Dimexide

6. Dmso

7. Rheumabene

8. Rimso

9. Rimso 100

10. Rimso 50

11. Rimso-50

12. Rimso50

13. Sclerosol

14. Sulfinylbis(methane)

15. Sulfoxide, Dimethyl

16. Sulphoxide, Dimethyl

2.3.2 Depositor-Supplied Synonyms

1. Dmso

2. 67-68-5

3. Methyl Sulfoxide

4. Methylsulfinylmethane

5. Dimethylsulfoxide

6. Dimethyl Sulphoxide

7. Methane, Sulfinylbis-

8. Demsodrox

9. Demasorb

10. Demavet

11. Dimexide

12. Domoso

13. Dromisol

14. Durasorb

15. Infiltrina

16. Somipront

17. Syntexan

18. Deltan

19. Demeso

20. Dolicur

21. Hyadur

22. Sulfinylbismethane

23. Dimethyl Sulfur Oxide

24. Dermasorb

25. Dipirartril-tropico

26. Doligur

27. Kemsol

28. Gamasol 90

29. Sulfinylbis(methane)

30. Rimso-50

31. Topsym

32. Dimethylsulphoxide

33. Dimethylsulfoxid

34. Sq 9453

35. Dimethylsulfoxyde

36. Rimso 50

37. Nsc-763

38. Sulfinylbis-methane

39. Caswell No. 381

40. Dimetil Sulfoxido

41. Methyl Sulphoxide

42. Dimethyli Sulfoxidum

43. Ccris 943

44. (methylsulfinyl)methane

45. (ch3)2so

46. Dms-90

47. Nsc 763

48. A 10846

49. Dimethyl-sulfoxide

50. S(o)me2

51. M 176

52. Methane, 1,1'-sulfinylbis-

53. Epa Pesticide Chemical Code 000177

54. Dms 70

55. Dms 90

56. Ai3-26477

57. Dmso, Sterile Filtered

58. Mfcd00002089

59. Chembl504

60. Sq-9453

61. Nsc763

62. Yow8v9698h

63. Dimethyl Sulfoxide, Hplc Grade

64. Chebi:28262

65. Dimethyl Sulfoxide, 99%

66. 103759-08-6

67. Topsym (rescinded)

68. Rimso-5

69. Domoso (veterinary)

70. Methylsulfoxide

71. Dimexidum

72. Sulfinyldimethane

73. Dimetilsolfossido

74. Dimetilsolfossido [dcit]

75. Dimethyl Sulpoxide

76. Fatty Acids, Tall-oil, Polymers With Me Epoxyoctadecanoate And Tetraethylenepentamine

77. Hsdb 80

78. Sulfoxide, Dimethyl

79. Methanesulfinylmethane

80. Dms-70

81. Dimethylsulfoxyde [inn-french]

82. Dimetil Sulfoxido [inn-spanish]

83. (methanesulfinyl)methane

84. Dimethyli Sulfoxidum [inn-latin]

85. Einecs 200-664-3

86. C2h6os

87. Unii-yow8v9698h

88. Diluent

89. Dimethysulfoxide

90. Dimethlysulfoxide

91. Dimethvlsulfoxide

92. Dimethyisulfoxide

93. Dimethylsulphoxid

94. Dimethy Sulfoxide

95. Dimetyl Sulfoxide

96. Dimethyisulphoxide

97. Dtxsid2021735

98. Dimethyl Sulfoxyde

99. Dimethyl-sulfoxyde

100. Dimethyl Suiphoxide

101. Dimethyl-sulphoxide

102. Dirnethyl Sulfoxide

103. Dimethyl Sulfoxixde

104. Methylsulfmylmethane

105. Dimethyl Sulf Oxide

106. Sulfinyl Bis(methane)

107. 2-thiapropane2-oxide

108. Dimethyl Sulfoxide [usan:usp:inn:ban]

109. Dimethylsulfoxide Solution

110. Methyl Sulfoxide (8ci)

111. Rimso-50 (tn)

112. Dimethyl Sulfoxide (dmso)

113. Dimethyl Sulfoxide(dmso)

114. Dmso (sterile-filtered)

115. Dmso [inci]

116. Dmso, Dimethyl Sulfoxide

117. Dsstox_cid_1735

118. Dimethyl Sulfoxide Solution

119. (dmso)

120. Dmso (dimethyl Sulfoxide)

121. Ec 200-664-3

122. Dsstox_rid_76298

123. H3c-so-ch3

124. Bidd:pxr0182

125. Dsstox_gsid_21735

126. Dimethyl Sulfoxide, >=99%

127. Dimethyl Sulfoxide, Anhydrous

128. Dimethyl Sulfoxide, For Hplc

129. Methane, Sulfinylbis- (9ci)

130. Wln: Os1&1

131. Dimethyl Sulfoxide [ii]

132. Dimethyl Sulfoxide [mi]

133. Dimethyl Sulfoxide [inn]

134. Dimethyl Sulfoxide [jan]

135. Dimethyl Sulfoxide, >=99.5%

136. Dimethyl Sulfoxide, Pcr Reagent

137. Dimethyl Sulfoxide [hsdb]

138. Dimethyl Sulfoxide [usan]

139. Dimethyl Sulfoxide, Acs Reagent

140. Methyl Sulfoxide, >=99%, Fg

141. Dimethyl Sulfoxide, P.a., 99%

142. Dimethyl Sulfoxide [vandf]

143. Dimethyl Sulfoxide, Lr, >=99%

144. Pharmakon1600-01506122

145. Dimethyl Sulfoxide [mart.]

146. Amy14894

147. Cs-b1637

148. Dimethyl Sulfoxide (jan/usp/inn)

149. Dimethyl Sulfoxide [usp-rs]

150. Dimethyl Sulfoxide [who-dd]

151. Hy-y0320

152. Methylsulfinylmethane [fhfi]

153. Zinc5224188

154. Tox21_300957

155. Bdbm50026472

156. Nsc760436

157. Stl264194

158. Dimethyl Sulfoxide, Ar, >=99.5%

159. Akos000121107

160. Ccg-213615

161. Db01093

162. Dimethyl Sulfoxide [green Book]

163. Dimethyl Sulfoxide, Analytical Standard

164. Nsc-760436

165. Cas-67-68-5

166. Dimethyl Sulfoxide [orange Book]

167. Mrf-0000764

168. (methanesulfinyl)methanedimethyl Sulfoxide

169. Dimethyl Sulfoxide [ep Monograph]

170. Dimethyl Sulfoxide, For Molecular Biology

171. Ncgc00163958-01

172. Ncgc00163958-02

173. Ncgc00163958-03

174. Ncgc00254859-01

175. Dimethyl Sulfoxide [usp Monograph]

176. Dimethyl Sulfoxide, Anhydrous, >=99.9%

177. Dimethyl Sulfoxide, Hplc Grade, 99.9%

178. Dimethyl Sulfoxide [for Spectrophotometry]

179. Dimethyl Sulfoxide, For Hplc, >=99.5%

180. Dimethyl Sulfoxide, For Hplc, >=99.7%

181. Ds-015031

182. D0798

183. D1159

184. D5293

185. Dimethyl Sulfoxide, Acs Reagent, >=99.9%

186. Dimethyl Sulfoxide, Aldrasorb(tm), 99.8%

187. Ft-0625099

188. Ft-0625100

189. D01043

190. Dimethyl Sulfoxide 1000 Microg/ml In Methanol

191. Dimethyl Sulfoxide Solution, 50 Wt. % In H2o

192. Dimethyl Sulfoxide, >=99.6%, Reagentplus(r)

193. Dimethyl Sulfoxide, Reagentplus(r), >=99.5%

194. Ab01563146_01

195. Dimethyl Sulfoxide (dmso), Cell Culture Reagent

196. Dimethyl Sulfoxide, P.a., Acs Reagent, 99.9%

197. Dimethyl Sulfoxide, Saj First Grade, >=99.0%

198. Dimethyl Sulfoxide 100 Microg/ml In Acetonitrile

199. Dimethyl Sulfoxide, Jis Special Grade, >=99.0%

200. Dimethyl Sulfoxide, Vetec(tm) Reagent Grade, 99%

201. Q407927

202. Dimethyl Sulfoxide, Uv Hplc Spectroscopic, 99.9%

203. Dimethyl Sulfoxide, Anhydrous, Zero2(tm), >=99.9%

204. Dimethyl Sulfoxide, Meets Ep, Usp Testing Specifications

205. Dimethyl Sulfoxide, Acs Spectrophotometric Grade, >=99.9%

206. Dimethyl Sulfoxide, Puriss. P.a., Dried, <=0.02% Water

207. 4h-1,3-oxazine,2-cyclopentyl-5,6-dihydro-4,4,7-trimethyl-

208. Dimethyl Sulfoxide, >=99.5% (gc), Plant Cell Culture Tested

209. Dimethyl Sulfoxide, Bioultra, For Molecular Biology, >=99.5% (gc)

210. Dimethyl Sulfoxide, European Pharmacopoeia (ep) Reference Standard

211. Dimethyl Sulfoxide, Puriss. P.a., Acs Reagent, >=99.9% (gc)

212. Dimethyl Sulfoxide, Vetec(tm) Reagent Grade, Anhydrous, >=99.7%

213. Dimethyl Sulfoxide, >=99.0%, Suitable For Absorption Spectrum Analysis

214. Dimethyl Sulfoxide, United States Pharmacopeia (usp) Reference Standard

215. Dimethyl Sulfoxide, For Inorganic Trace Analysis, >=99.99995% (metals Basis)

216. Dimethyl Sulfoxide, Meets Ep Testing Specifications, Meets Usp Testing Specifications

217. Dimethyl Sulfoxide, Hybri-max(tm), Sterile-filtered, Bioreagent, Suitable For Hybridoma, >=99.7%

218. Dimethyl Sulfoxide, Puriss., Absolute, Over Molecular Sieve (h2o <=0.005%), >=99.5% (gc)

219. Dimethyl Sulfoxide, Sterile-filtered, Bioperformance Certified, Meets Ep, Usp Testing Specifications, Suitable For Hybridoma

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 78.14 g/mol
Molecular Formula C2H6OS
XLogP3-0.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass78.01393598 g/mol
Monoisotopic Mass78.01393598 g/mol
Topological Polar Surface Area36.3 Ų
Heavy Atom Count4
Formal Charge0
Complexity29
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameDimethyl sulfoxide
PubMed HealthDimethyl Sulfoxide (Inside the bladder)
Drug ClassesRenal-Urologic Agent
Drug LabelRIMSO-50(dimethyl sulfoxide) (DMSO) 50% w/w Aqueous Solution for intravesical instillation.Each mL contains 0.54 gm dimethyl sulfoxide STERILE AND NON-PYROGENIC.Intravesical instillation for the treatment of interstitial cystitis.NOT FOR INTRAMUSCU...
Active IngredientDimethyl sulfoxide
Dosage FormSolution
RouteIntravesical
Strength50%
Market StatusPrescription
CompanyMylan Institutional

2 of 6  
Drug NameRimso-50
PubMed HealthDimethyl Sulfoxide (Inside the bladder)
Drug ClassesRenal-Urologic Agent
Drug LabelRIMSO-50(dimethyl sulfoxide) (DMSO) 50% w/w Aqueous Solution for intravesical instillation.Each mL contains 0.54 gm dimethyl sulfoxide STERILE AND NON-PYROGENIC.Intravesical instillation for the treatment of interstitial cystitis.NOT FOR INTRAMUSCU...
Active IngredientDimethyl sulfoxide
Dosage FormSolution
RouteIntravesical
Strength50%
Market StatusPrescription
CompanyMylan Institutional

3 of 6  
Drug NameSclerosol
PubMed HealthTalc (Intrapleural)
Drug ClassesSclerosing Agent
Active IngredientTalc
Dosage FormAerosol, metered
RouteIntrapleural
Strength400mg/spray
Market StatusPrescription
CompanyBryan

4 of 6  
Drug NameDimethyl sulfoxide
PubMed HealthDimethyl Sulfoxide (Inside the bladder)
Drug ClassesRenal-Urologic Agent
Drug LabelRIMSO-50(dimethyl sulfoxide) (DMSO) 50% w/w Aqueous Solution for intravesical instillation.Each mL contains 0.54 gm dimethyl sulfoxide STERILE AND NON-PYROGENIC.Intravesical instillation for the treatment of interstitial cystitis.NOT FOR INTRAMUSCU...
Active IngredientDimethyl sulfoxide
Dosage FormSolution
RouteIntravesical
Strength50%
Market StatusPrescription
CompanyMylan Institutional

5 of 6  
Drug NameRimso-50
PubMed HealthDimethyl Sulfoxide (Inside the bladder)
Drug ClassesRenal-Urologic Agent
Drug LabelRIMSO-50(dimethyl sulfoxide) (DMSO) 50% w/w Aqueous Solution for intravesical instillation.Each mL contains 0.54 gm dimethyl sulfoxide STERILE AND NON-PYROGENIC.Intravesical instillation for the treatment of interstitial cystitis.NOT FOR INTRAMUSCU...
Active IngredientDimethyl sulfoxide
Dosage FormSolution
RouteIntravesical
Strength50%
Market StatusPrescription
CompanyMylan Institutional

6 of 6  
Drug NameSclerosol
PubMed HealthTalc (Intrapleural)
Drug ClassesSclerosing Agent
Active IngredientTalc
Dosage FormAerosol, metered
RouteIntrapleural
Strength400mg/spray
Market StatusPrescription
CompanyBryan

4.2 Therapeutic Uses

Cryoprotective Agents; Free Radical Scavengers; Solvents

National Library of Medicine's Medical Subject Headings online file (MeSH, 2014); Available from, as of August 1, 2014: https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?term=Dimethyl%20sulfoxide


DMSO may have anti-inflammatory, antioxidant and analgesic activities. DMSO also readily penetrates cellular membranes.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 187


EXPL THER OBJECTIVE: To evaluate the discomfort and long-term efficacy associated with instillation of dimethyl sulfoxide (DMSO). MATERIAL AND METHODS: A total of 28 patients, 13 (11 females, 2 males) with classic interstitial cystitis (IC) and 15 (13 females, two males) with non-ulcer disease, who had received at least one series of six instillations of DMSO were studied. In addition to studying micturition diaries before and after the treatment, the evaluation included assessments of pain using a visual analog scale and of side-effects after each instillation in every series. Data were obtained by surveying the clinical records. A follow-up telephone interview was conducted for those patients who were treated with DMSO and in whom the treatment was considered successful. DMSO instillations were considered successful if the patient reported symptom amelioration and chose to continue with the treatment. RESULTS: Side-effects were not more common or pronounced in patients with classic compared to non-ulcer IC. For classic IC a significant difference could be seen when comparing side-effects experienced during the first three instillations and the three subsequent instillations. After DMSO instillations, a residual treatment effect lasting 16-72 months could be seen. CONCLUSIONS: Intravesical instillation therapy with DMSO appears to be a feasible treatment option for both subtypes of IC and is associated with a reasonably low degree of discomfort.

PMID:15764276 Rossberger J et al; Scand J Urol Nephrol. 39(1):73-7 (2005).


/Dimethyl sulfoxide is indicated/ for the symptomatic relief of patients with interstitial cystitis. /Included in US product labeling/

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 1067


For more Therapeutic Uses (Complete) data for DIMETHYL SULFOXIDE (12 total), please visit the HSDB record page.


4.3 Drug Warning

Onyx injection is a new technique for embolization of cerebral aneurysms that is involved in a controversy about the 'toxicity' of its solvent, dimethyl sulfoxide (DMSO). /The study/ retrospectively studied 38 patients treated for aneurysms with the liquid polymer, Onyx. Induction was with propofol, fentanyl and vecuronium, and anesthesia was maintained with isoflurane in O2 and N2O. The patients were given 500 mL of fluid after induction, and bradycardia was prevented in order to keep patients hyperdynamic. Electrocardiography (ECG), non-invasive blood pressure (NIBP), pulse oximetry, core temperatures, invasive blood pressure (BP), etCO2, and urine output were monitored throughout the intervention. Heart rate and BP changes in response to balloon inflation, DMSO injection, Onyx injection and balloon deflation were recorded. The patients were followed with serial neurological examinations, computerized tomography and/or magnetic resonance imaging postoperatively for evidence of any neurological injury. Cumulative DMSO doses were always well under previously implicated doses for systemic toxicity. No changes implicating toxic reactions were observed during DMSO and Onyx injections. Balloon-induced changes returned to baseline within 1 min of balloon deflation. Technique-related permanent morbidity occurred in two patients (worsening of cranial nerve palsies in one and monocular blindness in another) and intracranial hemorrhage with resulting death in one patient. All patients showed a tendency to oxygen desaturation, but this finding did not cause any clinical consequence. Anesthesiologists need to be vigilant in monitoring patients treated with techniques that are new or are being developed. /The study/ have seen no evidence of toxicity or any anesthetic complications in our group of patients, our only clinical concern being a tendency to oxygen desaturation, which may be explained by the inhalational elimination of DMSO.

PMID:15868171 Pamuk AG et al; Neuroradiology. 2005 May;47(5):380-6 (2005).


/This study/ describe/s/ the occurrence of the trigeminocardiac reflex (TCR) during DMSO pre-flushing of the microcatheter in preparation for Onyx embolization via the internal maxillary artery. TCR has not been previously associated with embolization of extradural entities. Familiarity with this clinical reflex and its proper management may help in planning neurointerventional procedures involving DMSO injection in the trigeminal territory.

PMID:21561553 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3278028 Puri AS et al; Interv Neuroradiol. 17(1):13-6 (2011).


Stem cell transplants are established therapy for hematologic and solid tumor malignancies. Known neurological complications of stem cell transplantation include CNS infection, seizures, strokes, metabolic encephalopathy, and hemorrhage. /This paper/ report/s/ two cases of autologous stem cell transplantation complicated by cerebral infarction and myocardial injury. /It is postulated/ that the cryopreservative dimethyl sulfoxide may be responsible.

PMID:17353475 Chen-Plotkin AS et al; Neurology. 68(11):859-61 (2007).


It is not known whether this drug is excreted in human milk ... caution should be exercised when dimethyl sulfoxide is administered to a nursing woman.

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 1068


For more Drug Warnings (Complete) data for DIMETHYL SULFOXIDE (20 total), please visit the HSDB record page.


4.4 Drug Indication

For the symptomatic relief of patients with interstitial cystitis.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dimethyl Sulfoxide may have anti-inflammatory, antioxidant and analgesic activities. Dimethyl Sulfoxide also readily penetrates cellular membranes. The membrane-penetrating ability of dimethyl sulfoxide may enhance diffusion of other substances through the skin. For this reason, mixtures of idoxuridine and dimethyl sulfoxide have been used for topical treatment of herpes zoster in the United Kingdom.


5.2 MeSH Pharmacological Classification

Cryoprotective Agents

Substances that provide protection against the harmful effects of freezing temperatures. (See all compounds classified as Cryoprotective Agents.)


Solvents

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)


Free Radical Scavengers

Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)


5.3 ATC Code

G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BX - Other urologicals

G04BX13 - Dimethyl sulfoxide


M - Musculo-skeletal system

M02 - Topical products for joint and muscular pain

M02A - Topical products for joint and muscular pain

M02AX - Other topical products for joint and muscular pain

M02AX03 - Dimethyl sulfoxide


5.4 Absorption, Distribution and Excretion

Absorption

Readily and rapidly absorbed following administration by all routes and distributed throughout the body.


Route of Elimination

Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.


Following topical application, DMSO is absorbed and widely distributed in tissue and body fluids. DMSO and dimethyl sulfone are excreted in the urine and feces. DMSO is eliminated through the breath and skin and is responsible for the characteristic garlic odor. ... Dimethyl sulfone can persist in serum > 2 weeks after a single intravesical instillation. No residual accumulation of DMSO has occurred after treatment from protracted periods of time.

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 720


Dimethyl sulfoxide and /one of its metabolites/ dimethyl sulfone, are excreted in the urine and feces. Dimethyl sulfide /another metabolite/ is eliminated through the breath and skin...

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 1067


By use of a Fourier transform infrared (FTIR) spectroscopic imaging technique, /this study examined/ the dynamic optical clearing processes occurring in hyperosmotically biocompatible agents penetrating into skin tissue in vitro. The sequential collection of images in a time series provides an opportunity to assess penetration kinetics of dimethyl sulphoxide (DMSO) and glycerol beneath the surface of skin tissue over time. From 2-D IR spectroscopic images and 3-D false color diagrams, ...show/s/ that glycerol takes at least 30 min to finally penetrate the layer of epidermis, while DMSO can be detected in epidermis after only 4 min of being topically applied over stratum corneum sides of porcine skin. The results demonstrate the potential of a FTIR spectroscopic imaging technique as an analytical tool for the study of dynamic optical clearing effects when the bio-tissue is impregnated by hyperosmotically biocompatible agents such as glycerol and DMSO.

PMID:18465954 Jiang J et al; J Biomed Opt. 13(2):021105 (2008).


In man radioactivity of 35S DMSO appeared in blood 5 min after cutaneous application. One hour later, radioactivity could detected in bones.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Dimethyl sulfoxide. Available from, as of June 7, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


For more Absorption, Distribution and Excretion (Complete) data for DIMETHYL SULFOXIDE (9 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Dimethyl sulfoxide is metabolized in man by oxidation to dimethyl sulfone or by reduction in dimethyl sulfide. Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.


Dimethyl sulfoxide is metabolized in man by oxidation to dimethyl sulfone or by reduction to dimethyl sulfide.

Drug Facts and Comparisons 2013. Wolters Kluwer Health St. Louis, MO 2013, p. 1067


Autoimmune strain MRL/Ipr, C3H/lpr, and male BXSB mice were placed on a continuous treatment regimen with 3% DMSO or 3% DMS02 in the drinking water, ad libitum, commencing at 1 to 2 months of age, before spontaneous autoimmune lymphoproliferative disease development could be detected. This represented doses of 8-10 g/kg/day of DMSO and 6-8 g/kg/day of DMS02. Both compounds were observed to extend the mean life span of MRL/Ipr mice from 5.5 months to over 10 months of age. All strains showed decreased antinuclear antibody responses and significant diminution of lymphadenopathy, splenomegaly, and anemia development. Serum IgG levels and spleen IgM antibody plaque formation, however, did not differ from control values. There was no indication of involvement of systemic immunosuppressive or antiproliferative effects, and treated animals were observed to remain healthy and vigorous with no signs of toxicity. These results demonstrate that high doses of both DMSO and its major in vivo metabolite, DMSO2, provide significant protection against the development of murine autoimmune lymphoproliferative disease.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Dimethyl sulfoxide. Available from, as of June 7, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


In man, DMSO is oxidized into dimethylsulfone DMSO2, metabolite excreted by urine (17-22 %). DMSO is reduced into dimethylsulfide, DMS, a volatile metabolite, responsible for garlic odour of exhaled air (1 %). About 85 % is excreted unchanged, both by urine (50 %) and feces (50 %).

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Dimethyl sulfoxide. Available from, as of June 7, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


5.6 Biological Half-Life

Unchanged DMSO has a half-life of 12 to 15 hours.

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 720


/The/ half-life /of DMSO in the rhesus monkey/ was calculated to be about 38 hrs and its elimination rate constant equaled 0.018, or about 2% per hr.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Dimethyl sulfoxide. Available from, as of June 7, 2005: https://www.epa.gov/hpv/pubs/hpvrstp.htm


5.7 Mechanism of Action

The mechanism of dimethyl sulfoxide's actions is not well understood. Dimethyl sulfoxide has demonstrated antioxidant activity in certain biological settings. For example, the cardiovascular protective effect of dimethyl sulfoxide in copper-deficient rats is thought to occur by an antioxidant mechanism. It is also thought that dimethyl sulfoxide's possible anti-inflammatory activity is due to antioxidant action.


Thioacetamide (400 mg/kg body weight, i.p.) was administered to rats. After 12 hr the activity of plasma glutamate-oxaloacetate transaminase (GOT) and glutamate-pyruvate transaminase (GPT) was significantly higher than that of the control group, and after 24 hr plasma GOT and GPT activities strongly increased. These results indicated that the necrotic process was initiated at about 12 hr and developed thereafter. By co-administration of dimethyl sulphoxide (DMSO, 18 and 1 hr before, and 8 hr after administration of thioacetamide: each time, 2.5 mL/kg body weight, p.o.), plasma GOT and GPT were significantly decreased and were even comparable to the control group, showing that DMSO totally prevented the necrotic action of thioacetamide. After 12 and 24 hr of thioacetamide administration, the hepatic level of vitamin C, the most sensitive chemical indicator of oxidative stress, decreased significantly, indicating that oxidative stress was significantly enhanced 12 hr after thioacetamide intoxication and thereafter. DMSO totally restored the liver vitamin C level, demonstrating that DMSO effectively ameliorated the oxidative stress caused by thioacetamide, resulting in the prevention of necrosis of the liver. Phosphorylated c-Jun NH(2)-terminal kinase (JNK) significantly increased transiently 12 hr after treatment with thioacetamide. These results indicated that oxidative stress and the activation of JNK took place almost simultaneously. Phosphorylated extracellular signal-related kinase (ERK) 2 was significantly increased 6-12 hr after thioacetamide injection. Phosphorylated p38 MAPK (mitogen activated protein kinase) was significantly decreased 24 hr after administration of thioacetamide. DMSO treatment inhibited the change of these MAPKs by thioacetamide, corresponding with the prevention of the liver necrosis as well as the attenuation of oxidative stress.

PMID:17395177 Kishioka T et al; Eur J Pharmacol 564 (1-3): 190-5 (2007)


Previous studies performed in our laboratory indicated that non-toxic concentrations of peroxynitrite nevertheless commit U937 cells to a rapid necrosis that is however prevented by a survival signaling driven by cytosolic phospholipase A(2)-released arachidonic acid. Toxicity was mediated by concentrations of peroxynitrite resulting in H(2)O(2)-dependent inhibition of arachidonic acid release. The present study shows that U937 cells differentiated to monocytes by prolonged exposure to dimethyl sulfoxide are resistant to peroxynitrite because able to respond with enhanced release of arachidonic acid. An additional important observation was that these cells require more arachidonate than the undifferentiated cells to support the survival signaling. The enhanced arachidonic acid release was not associated with changes in cytosolic phospholipase A(2) expression but was rather dependent on the increased responsiveness of the enzyme to calcium-dependent stimulation as well as on reduced mitochondrial formation of H(2)O(2). The latter event was found to be critical, since differentiated and undifferentiated cells were equally sensitive to peroxynitrite when the accumulation of H(2)O(2) was enhanced via depletion of catalase, or addition of a complex III inhibitor. Thus, the strategy selected by the differentiation process to allow monocytes to cope with peroxynitrite appears to involve some specific mechanism preventing the mitochondrial formation of H(2)O(2).

PMID:16103003 Guidarelli A et al; Int J Biochem Cell Biol. 38(1):56-68 (2006).


Dimethyl sulfoxide (DMSO) has recently been proposed as an anti-inflammatory and free radical scavenging agent. However, the mechanisms by which DMSO mediates its therapeutic effects are unclear. /This paper/ investigated the capability of DMSO to up-regulate heme oxygenase-1(HO-1) expression, as well as the possible underlying mechanisms in human umbilical vein endothelial cells (HUVECs). DMSO induced HO-1 expression both at the level of mRNA and protein in dose-and time-dependent manners in HUVECs, resulting in increased HO-1 activity. The pharmacological inhibition of cJun-N-terminal kinases (JNKs) blocked the DMSO-induced HO-1 up-regulation, while inhibition of extracellular regulated kinase and p38-MAPK did not block heme oxygenase-1 up-regulation. In addition, the phosphorylation of JNKs was initiated by DMSO, indicating the involvement of this kinase in the observed response. DMSO increased the nuclear translocation of NF-E2-related factor 2 (Nrf2) and enhanced its binding to the anti-oxidant response element. Inhibition of Nrf2 synthesis by small interfering RNA molecules subsequently inhibited HO-1 expression induced by DMSO, indicating DMSO's role in inducing HO-1 expression via Nrf2 activation. Utilizing these findings, the present study identified DMSO as a novel inducer of HO-1 expression and identified the underlying mechanisms involved in this process.

PMID:21533649 Liang C et al; Mol Cell Biochem. 355(1-2):109-15 (2011).


Dimethyl sulfoxide (DMSO) is evident to induce apoptosis in certain tumor cells in vitro. However, its apoptotic mechanism remains unexplored in in vivo tumors. This article describes that DMSO, being non-toxic to the normal lymphocytes, up regulated TNFalpha and p53, declined Bcl-2/Bax ratio, activated caspase 9 and PARP-1 cleavage and produced apoptotic pattern of DNA ladder in Dalton's lymphoma (DL) in vivo. This was consistent with the declined expressions of tumor growth supportive glycolytic enzymes; inducible D-fructose-6-phosphate-2-kinase and lactate dehydrogenase-5 in the DL cells. The findings suggest induction of TNFalpha-p53-mitochondrial pathway of apoptosis by DMSO in a non-Hodgkin's lymphoma and support evolving concept of glycolytic inhibition led apoptosis in a tumor cell in vivo.

PMID:21269693 Koiri RK and Trigun SK. Leuk Res. 35(7):950-6 (2011).