Physicochemical Properties
| Molecular Formula | C2H6O2S |
| Molecular Weight | 94.13 |
| Exact Mass | 94.008 |
| Elemental Analysis | C, 25.52; H, 6.43; O, 33.99; S, 34.06 |
| CAS # | 67-71-0 |
| Related CAS # | Dimethyl sulfone-d6;22230-82-6 |
| PubChem CID | 6213 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 240.9±8.0 °C at 760 mmHg |
| Melting Point | 107-109 °C(lit.) |
| Flash Point | 143.3±0.0 °C |
| Vapour Pressure | 0.1±0.5 mmHg at 25°C |
| Index of Refraction | 1.402 |
| LogP | -1.19 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 5 |
| Complexity | 85.3 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CS(=O)(=O)C |
| InChi Key | HHVIBTZHLRERCL-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3 |
| Chemical Name | methylsulfonylmethane |
| Synonyms | Dimethyl sulfone; Methyl sulfone; Methylsulfonylmethane; DIMETHYLSULFONE; Dimethyl sulphone; Methane, sulfonylbis-; sulfonyldimethane; ...; 67-71-0; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Microbial Metabolite; Endogenous Metabolite; Free radical scavenging (hydroxyl radical trapping); Prostaglandin receptor inhibition |
| ln Vitro |
Cultured bovine chorionic capillary endothelial cells (CCE) are not able to proliferate when exposed to dimethyl adsorbent (25 mM/mL, gradient 15.5 μL/mL; 24 h) [2].
DMSO alone (15.5 μl/ml) significantly inhibited proliferation of bovine choricoapillary endothelial cells (CCE) after 24-hour incubation, reducing cell count to 2.4 × 10⁴ cells/ml (vs. unsupplemented control: 3.8 × 10⁴ cells/ml; p<0.001). This inhibitory effect was statistically indistinguishable from 100 μg/ml thalidomide dissolved in equivalent DMSO (p=0.74). Prior studies using DMSO as solvent for thalidomide in human umbilical vein endothelial cells (HUVEC) showed no inhibition by DMSO alone (contrasting with bovine CCE results).[2] |
| ln Vivo |
It has been demonstrated that xylene (0, 0.01, 0.03, 0.1, 0.3, 1.0 mL; i.p.; single Manhattan) has a neuroprotective effect and dramatically lowers the volume of circuit infarct [3].
In Vivo [3] Rat permanent MCA occlusion model: • Intraperitoneal injection of DMSO (0.1, 0.3, 1.0 ml) 30 min pre-ischemia significantly reduced infarction volume at 24h vs. saline controls (P<0.05). • Doses ≤0.03 ml showed no significant neuroprotection. Previous models: - Reduced mortality in rhesus monkey brain compression model. - Improved blood flow in rhesus monkey missile brain injury. - Conflicting results: Reduced infarction in canine MCA emboleotomy but increased infarction in gerbil carotid occlusion model. |
| Cell Assay |
Cell Assay [2] Cell type: Bovine choricoapillary endothelial cells (CCE) Protocol: 1. Isolated CCE cells (passage 2-3) seeded at 2×10⁴ cells/ml in gelatin-coated 24-well plates. 2. After 24h, medium replaced with: o Experimental: 100 μg/ml thalidomide in DMSO (final DMSO: 15.5 μl/ml) o Control 1: DMSO alone (15.5 μl/ml) o Control 2: Unspplemented medium 3. Incubated 24h at 37°C/5% CO₂. 4. Cells detached using trypsin-EDTA, fixed in paraformaldehyde, counted manually. |
| Animal Protocol |
Animal Protocol [3] Species: Male Sprague-Dawley rats (275–300 g) Procedure: 1. Anesthetized with 4% isoflurane (70% N₂O/30% O₂), intubated. 2. Maintained at 37°C rectal/temporalis temperature. 3. Femoral artery cannulated for blood pressure/blood gas monitoring. 4. Permanent MCA occlusion via intraluminal suture (20–22 mm insertion). Dosing: DMSO (0.01–1.0 ml in saline, total vol. 1.0 ml) administered intraperitoneally 30 min pre-occlusion. Endpoint: Brains harvested at 24h, sectioned (2 mm), stained with 2% TTC. Infarction volume quantified by blinded digital image analysis. |
| ADME/Pharmacokinetics | Distribution: Rapid whole-body distribution including brain penetration. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Dimethyl sulfone (methylsulfonylmethane, MSM) is a normal oxidative metabolite found in the bloodstream and breastmilk. It is a metabolic product of endogenous methanethiol metabolism and intestinal bacterial metabolism. No studies have been done on the use of dimethyl sulfone (MSM) orally in nursing mothers, but its low toxicity indicates that it is unlikely to harm the breastfed infant. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Dimethyl Sulfone. 2022 Mar 21. [2]. DMSO mimics inhibitory effect of thalidomide on choriocapillary endothelial cell proliferation in culture. Br J Ophthalmol. 2002 Nov;86(11):1303-5. [3]. Dimethylsulfoxide (DMSO) treatment reduces infarction volume after permanent focal cerebral ischemia in rats. Neurosci Lett. 1997 Dec 19;239(2-3):125-7. |
| Additional Infomation |
Sulfonyldimethane is a sulfone. Dimethyl sulfone has been reported in Equisetum arvense, Basella alba, and other organisms with data available. See also: Dimethyl sulfone; menthol (component of); Dimethyl sulfone; N-acetylglucosamine (component of); Arnica montana flower; dimethyl sulfone; menthol (component of) ... View More ... DMSO is commonly used as solvent for water-insoluble compounds (e.g., thalidomide). This study demonstrates its direct anti-proliferative effect on bovine CCE cells, confounding interpretation of thalidomide experiments without proper solvent controls. Mechanism: Species-specific effects suspected; metabolites may contribute to inhibition. Research implication : In vitro studies using thalidomide/DMSO solutions require parallel DMSO-only controls to differentiate drug effects from solvent artifacts. |
Solubility Data
| Solubility (In Vitro) | H2O : ~50 mg/mL (~531.18 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 10.6236 mL | 53.1180 mL | 106.2361 mL | |
| 5 mM | 2.1247 mL | 10.6236 mL | 21.2472 mL | |
| 10 mM | 1.0624 mL | 5.3118 mL | 10.6236 mL |