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Dimethyl sulfone

Alias: Dimethyl sulfone; Methyl sulfone; Methylsulfonylmethane; DIMETHYLSULFONE; Dimethyl sulphone; Methane, sulfonylbis-; sulfonyldimethane; ...; 67-71-0;
Cat No.:V38602 Purity: ≥98%
Dimethylsulfone (methylsulfonylmethane) is a metabolite of endogenous methylmercaptan metabolism and intestinal bacterial metabolism.
Dimethyl sulfone
Dimethyl sulfone Chemical Structure CAS No.: 67-71-0
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Dimethyl sulfone:

  • Dimethyl sulfone-d6
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Dimethylsulfone (methylsulfonylmethane) is a metabolite of endogenous methylmercaptan metabolism and intestinal bacterial metabolism. Dimethyl sulfone suppresses the proliferation/growth of chorionic capillary endothelial cells, and also has anti~inflammatory, antioxidant, and local anesthetic effects with neuro-protective (neuro-protection) effects.
Biological Activity I Assay Protocols (From Reference)
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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
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)
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 : PEG300Tween 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).
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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 : PEG300Tween 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).
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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

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
The Effect of Methylsulfonylmethane (MSM) on Cardiometabolic Health
CTID: NCT03716791
Phase: N/A
Status: Completed
Date: 2021-10-05
Methylsulfonylmethane on Knee Laxity
CTID: NCT03747198
Phase: N/A
Status: Completed
Date: 2020-06-01
Effect of Methyl-Sulphonyl-Methane on Osteoarthritis and Cartilage
CTID: NCT01836757
Phase: Phase 1
Status: Unknown status
Date: 2013-04-22
Efficacy of Methylsulfonylmethane Supplementation on Osteoarthritis of The Knee: A Randomized Controlled Study
CTID: NCT01188213
Phase: N/A
Status: Completed
Date: 2010-08-25
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