Cannabis Compound Database: Showing Compound Card for Dimethylsulfone (CDB000596)

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Record Information

Version

1.0

Created at

2020-03-19 00:45:45 UTC

Updated at

2020-12-07 19:07:33 UTC

CannabisDB ID

CDB000596

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dimethylsulfone

Description

Dimethyl sulfone (DMSO2), also known as sulfonylbismethane, belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group, with the general structure RS(=O)2R' (R,R' =alkyl, aryl). It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages and it is marketed as a dietary supplement. This colorless solid features a sulfonyl functional group and is considered relatively inert chemically. Dimethyl sulfone reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. Dimethyl sulfone is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a metabolite occurring in plasma and cerebrospinal fluid of normal humans. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism (PMID: 15996001 ). It is sometimes used as a cutting agent for illicitly manufactured methamphetamine. Because of its polarity and thermal stability, Dimethyl sulfone is used industrially as a high-temperature solvent for both inorganic and organic substances. Dimethyl sulfone is also commonly found in the atmosphere above marine areas, where it is used as a carbon source by the airborne bacteria Afipia (PMID: 23359712 ). It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dimethyl sulphone	ChEBI
Methylsulfonylmethane	ChEBI
Sulfonylbismethane	ChEBI
Sulphonylbismethane	ChEBI
Methylsulphonylmethane	Generator
Dimethyl sulfone, 13C-labeled	MeSH
Methyl sulfone	MeSH
Methyl sulfonmethane	MeSH
(Methylsulfonyl)methane	HMDB
Dimethylsulfone	HMDB
Lignisul MSM	HMDB
Opti MSM	HMDB
Sulfonylbis-methane	HMDB
Dimethyl sulfone	ChEBI
Sulphonyldimethane	Generator, HMDB

Chemical Formula

C₂H₆O₂S

Average Molecular Weight

94.13

Monoisotopic Molecular Weight

94.0089

IUPAC Name

methanesulfonylmethane

Traditional Name

methylsulfonylmethane

CAS Registry Number

67-71-0

SMILES

CS(C)(=O)=O

InChI Identifier

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

InChI Key

HHVIBTZHLRERCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfonyls

Sub Class

Sulfones

Direct Parent

Sulfones

Alternative Parents

Substituents

Sulfone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfone (CHEBI:9349 )
a sulfone (CPD-10437 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Microbe:

Afipia

Biological location:

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Biological role:

Molecular messenger:

Signaling molecule

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	109 °C	Not Available
Boiling Point	248 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	-1.41	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.95	ALOGPS
logP	-1.3	ChemAxon
logS	-0.23	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.53 m³·mol⁻¹	ChemAxon
Polarizability	8.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dimethylsulfone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002f-9000000000-3e72edc8bd8e168298a0	Spectrum
Predicted GC-MS	Dimethylsulfone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dimethylsulfone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-9000000000-9896ec507f104ada81f3	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-aad0ad2e46e9a93df295	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-8cb5ee5ae152833c1e84	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-fb26633c75e592809868	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-3a6db80e12370ab204a9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9000000000-c5c35fbdd4193d0ece0d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-c0a7fe921fa7e601fb70	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-113ab821ffdae95a6086	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fu-9000000000-2ef5cb880f6a43bd9df3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-f0302cfc5bddee62ebdf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-f0302cfc5bddee62ebdf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-902b68745378a21a3ae9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-dd5ad5c474bf2a0fc2ab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-dd5ad5c474bf2a0fc2ab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-d82cbf78ceb7825835f9	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0004983

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006725

KNApSAcK ID

Not Available

Chemspider ID

5978

KEGG Compound ID

C11142

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylsulfonylmethane

METLIN ID

7236

PubChem Compound

6213

PDB ID

Not Available

ChEBI ID

9349

References

General References

Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. doi: 10.1002/nbm.966. [PubMed:15996001 ]
DeLeon-Rodriguez N, Lathem TL, Rodriguez-R LM, Barazesh JM, Anderson BE, Beyersdorf AJ, Ziemba LD, Bergin M, Nenes A, Konstantinidis KT: Microbiome of the upper troposphere: species composition and prevalence, effects of tropical storms, and atmospheric implications. Proc Natl Acad Sci U S A. 2013 Feb 12;110(7):2575-80. doi: 10.1073/pnas.1212089110. Epub 2013 Jan 28. [PubMed:23359712 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for Dimethylsulfone (CDB000596)

Structure for CDB000596 (Dimethylsulfone)