DIMETHYL SULFONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C2H6O2S
Molecular Weight	94.133
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(C)(=O)=O

InChI

InChIKey=HHVIBTZHLRERCL-UHFFFAOYSA-N

InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3

HIDE SMILES / InChI

Molecular Formula	C2H6O2S
Molecular Weight	94.133
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28300758 | https://www.ncbi.nlm.nih.gov/pubmed/12387309 | https://www.ncbi.nlm.nih.gov/pubmed/12370155

DIMETHYL SULFONE is a compound that contains sulfur. It is a naturally occurring organosulfur compound utilized as a complementary and alternative medicine (CAM) under a variety of names including dimethyl sulfone, methyl sulfone, sulfonylbismethane, organic sulfur, or crystalline dimethyl sulfoxide. Its most common use is as anti-inflammatory agent. DIMETHYL SULFONE has been claimed to relieve stress, relieve pain, treat parasitic infections, increase energy, boost metabolism, enhance circulation, and improve wound healing, but there is little supporting scientific evidence. Due to its enhanced ability to penetrate membranes and permeate throughout the body, the full mechanistic function of MSM may involve a collection of cell types and is therefore difficult to elucidate. DIMETHYL SULFONE is recognized as safe by the FDA, but efficacy has yet to be proven. In rats, no adverse events were observed after daily doses of 2 g MSM per kg of body weight. Published clinical trials of DIMETHYL SULFONE did not report any serious side effects, but long-term effects are unknown.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dietary Supplements 1 Sources: https://www.drugs.com/international/dimethyl-sulfone.html https://www.webmd.com/vitamins/ai/ingredientmono-522/msm-methylsulfonylmethane http://www.mims.com/india/drug/info/glucosamine/	Palliative		Approved 8583	ARTHRONSAN Approved Use Unknown Launch Date 2018
Osteoarthritis 157 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fefb555f-ef66-4020-826d-002c76df0225&type=display	Inactive ingredient		Approved 8583	Meloxicam Approved Use Meloxicam is a non-steroidal anti-inflammatory drug indicated for: Osteoarthritis (OA) ( 1.1) Rheumatoid Arthritis (RA) Launch Date 2010

Doses

Dose	Population	Adverse events
2.6 g 2 times / day multiple, oral Studied dose Dose: 2.6 g, 2 times / day Route: oral Route: multiple Dose: 2.6 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12006124/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12006124/	Disc. AE: Urticaria... AEs leading to discontinuation/dose reduction: Urticaria (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/12006124/

AEs

AE	Significance	Dose	Population
Urticaria	2% Disc. AE	2.6 g 2 times / day multiple, oral Studied dose Dose: 2.6 g, 2 times / day Route: oral Route: multiple Dose: 2.6 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12006124/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12006124/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 OATP1B3 961 OATP1B1 1079 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 1.0	inconclusive [IC50 19.9526 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 62.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 63.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 62.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 62.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 32.0	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 33.0	yes [Inhibition 10 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/6213#section=Biological-Test-Results Page: 63.0

PubMed

Title	Date	PubMed
Yeast as a model system for identification of metabolic targets of a 'glucosamine complex' used as a therapeutic agent of osteoarthritis.	2008-11	18662850
Systematic review of the nutritional supplements dimethyl sulfoxide (DMSO) and methylsulfonylmethane (MSM) in the treatment of osteoarthritis.	2008-11	18417375
Why are dimethyl sulfoxide and dimethyl sulfone such good solvents?	2008-08	18458968
A cohort study of in utero polychlorinated biphenyl (PCB) exposures in relation to secondary sex ratio.	2008-07-15	18627595
Combined effects of silymarin and methylsulfonylmethane in the management of rosacea: clinical and instrumental evaluation.	2008-03	18254805
A natural mineral supplement provides relief from knee osteoarthritis symptoms: a randomized controlled pilot trial.	2008-02-17	18279523
Effect of a natural extract of chicken combs with a high content of hyaluronic acid (Hyal-Joint) on pain relief and quality of life in subjects with knee osteoarthritis: a pilot randomized double-blind placebo-controlled trial.	2008-01-21	18208600
Dietary supplements for osteoarthritis.	2008-01-15	18246887
Photochemistry of iron in simulated crustal aerosols with dimethyl sulfide oxidation products.	2008-01-01	18350887
Synthesis of 4-aminotropones from [(sulfinyl or sulfonyl)methyl]-substituted p-quinamines.	2008	17918757
Relationship between aryl hydrocarbon receptor-affinity and the induction of EROD activity by 2,3,7,8-tetrachlorinated phenothiazine and derivatives.	2007-10-15	17761204
The ptsP gene encoding the PTS family protein EI(Ntr) is essential for dimethyl sulfone utilization by Pseudomonas putida.	2007-10	17711452
Transcriptional regulation of the sulfate-starvation-induced gene sfnA by a sigma54-dependent activator of Pseudomonas putida.	2007-09	17768252
Maternal and cord serum exposure to PCB and DDE methyl sulfone metabolites in eastern Slovakia.	2007-09	17574648
Comparative QSAR modeling of COX-2 inhibitor 1,2-diarylimidazoles using E-state and physicochemical parameters.	2007-06	17650586
Catalytic oxidation processes for removing dimethylsulfoxide from wastewater.	2007-06	17320930
Oral developmental toxicity study of methylsulfonylmethane in rats.	2007-06	17258373
Metalation of cyclic pseudopeptidic thiosulfinates with Ni(II) and Zn(II) after ring opening: a mechanistic investigation.	2007-05-28	17465540
Pharmacokinetics and distribution of [35S]methylsulfonylmethane following oral administration to rats.	2007-02-07	17263509
Polychlorinated biphenyls and their hydroxylated metabolites (OH-PCBS) in pregnant women from eastern Slovakia.	2007-01	17366814
Dual carbonic anhydrase--cyclooxygenase-2 inhibitors.	2007	17504133
Enantioselective formation of methyl sulfone metabolites of 2,2',3,3',4,6'-hexachlorobiphenyl in rat.	2006-12-15	17256508
Methylsulfonylmethane (MSM) ingestion causes a significant resonance in proton magnetic resonance spectra of brain and cerebrospinal fluid.	2006-10	17236113
Levels of PCBs and their metabolites in the serum of residents of a highly contaminated area in eastern Slovakia.	2006-06-15	16830529
Elemental sulfur identified in urine of cheetah, Acinonyx jubatus.	2006-06	16541335
Clinical and instrumental evaluation of skin improvement after treatment with a new 50% pyruvic acid peel.	2006-04	16681660
Managing ichthyosis: a case study.	2006-04	16636365
Efficacy of methylsulfonylmethane (MSM) in osteoarthritis pain of the knee: a pilot clinical trial.	2006-03	16309928
Synthesis and characterization of a new cutinase substrate, 4-nitrophenyl (16-methyl sulfone ester) hexadecanoate.	2006-02-10	16183160
Studies of the condensation of sulfones with ketones and aldehydes.	2006-01-20	16408963
Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression.	2006-01	16459255
Supplement may ease pain of knee osteoarthritis.	2006-01	16447314
Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence.	2006	16859534
Chlorinated hydrocarbon contaminants and metabolites in polar bears (Ursus maritimus) from Alaska, Canada, East Greenland, and Svalbard: 1996-2002.	2005-12-01	16115663
Investigation of iminosulfuranes as novel transdermal penetration enhancers: enhancement activity and cytotoxicity.	2005-11	16132348
Liquid chromatography-mass spectrometry using the hydrogen/deuterium exchange reaction as a tool for impurity identification in pharmaceutical process development.	2005-10-25	15990368
Impact of polychlorinated biphenyls contamination on estrogenic activity in human male serum.	2005-10	16203234
"Cooking the sample": radiofrequency induced heating during solid-state NMR experiments.	2005-09	16221542
Molecular detection and isolation from antarctica of methylotrophic bacteria able to grow with methylated sulfur compounds.	2005-08	16104352
Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR.	2005-08	15996001
Influence of resonance on the acidity of sulfides, sulfoxides, sulfones, and their group 16 congeners.	2005-06-09	16833845
Kinetics studies of aqueous phase reactions of Cl atoms and Cl2(-) radicals with organic sulfur compounds of atmospheric interest.	2005-05-05	16833708
Analysis of one-dimensional pure-exchange NMR experiments for studying dynamics with broad distributions of correlation times.	2005-04-15	15945644
Evidence of interaction between polychlorinated biphenyls and phthalates in relation to human sperm motility.	2005-04	15811833
Catalytic ozonation of gaseous reduced sulfur compounds using wood fly ash.	2005-03-15	15819244
The sigma54-dependent transcriptional activator SfnR regulates the expression of the Pseudomonas putida sfnFG operon responsible for dimethyl sulphone utilization.	2005-02	15661012
Isolation and properties of methanesulfonate-degrading Afipia felis from Antarctica and comparison with other strains of A. felis.	2005-01	15643932
Randomised, Double-Blind, Parallel, Placebo-Controlled Study of Oral Glucosamine, Methylsulfonylmethane and their Combination in Osteoarthritis.	2004	17516722
Isolation of dimethyl sulfone-degrading microorganisms and application to odorless degradation of dimethyl sulfoxide.	2004	16233595
Oxidative degradation of dimethyl sulfoxide by Cryptococcus humicolus WU-2, a newly isolated yeast.	2003	16233376

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:27 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:27 GMT 2025`
Record UNII	9H4PO4Z4FT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMETHYL SULFONE

Official Name

English

METHYLSULFONYLMETHANE

Preferred Name

English

MSM

Code

English

Methylsulfonylmethane [WHO-DD]

Common Name

English

DIMETHYL SULFONE [MI]

Common Name

English

METHYLSULFONYLMETHANE [VANDF]

Common Name

English

MYTHYLSULFONYLMETHANE (MSM) [VANDF]

Common Name

English

METHYL SULFONE

Systematic Name

English

DIMETHYL SULPHONE

Systematic Name

English

DIMETHYL SULFONE [MART.]

Common Name

English

METHYLSULFONYLMETHANE [USP-RS]

Common Name

English

METHOSULFONYLMETHANE

Common Name

English

NSC-63345

Code

English

DIMETHYL SULFOXIDE IMPURITY A [EP IMPURITY]

Common Name

English

METHYL SULPHONE

Systematic Name

English

Classification Tree Code System Code

DSLD

651 (Number of products:1171)