Human Metabolome Database Version 3.5

Showing metabocard for Dimethyl sulfoxide (HMDB02151)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:38 -0600
Update Date 2013-05-17 15:58:10 -0600
HMDB ID HMDB02151
Secondary Accession Numbers None
Metabolite Identification
Common Name Dimethyl sulfoxide
Description Dimethyl sulfoxide (DMSO) is a key dipolar aprotic solvent. It is less toxic than other members of this class: dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA. Dimethyl sulfoxide is the chemical compound (CH3)2SO. This colorless liquid is an important "dipolar aprotic solvent." It is readily miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, allowing the handler to taste it. Some describe it as an "oyster-like" taste, others claim it tastes like garlic. DMSO is also employed as a rinsing agent in the electronics industry and, in its deuterated form (DMSO-d6), is a useful solvent in NMR due to its ability to dissolve a wide range of chemical compounds and its minimal interference with the sample signals. In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cell, which are often frozen in a mixture of 10% DMSO and 90% fetal calf serum. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cell. Dimethyl sulfoxide is a by-product of wood pulping. One of the leading suppliers of DMSO is the Gaylord company in the USA. DMSO is frequently used as solvent in a number of chemical reactions. In particular it is an excellent reaction solvent for SN2 alkylations: it is possible to alkylate indoles with very high yields using potassium hydroxide as the base and a similar reaction also occurs with phenols. DMSO can be reacted with methyl iodide to form a sulfoxonium ion which can be reacted with sodium hydride to form a sulfur ylide. The methyl groups of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the resultant anions by the sulfoxide group.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (methylsulfinyl)methane
  2. Dimethyl sulfoxide
  3. Dimethyl sulfoxixde
  4. Dimethyl sulfur oxide
  5. Dimethyl sulphoxide
  6. Dimethyl sulpoxide
  7. DMSO
Chemical Formula C2H6OS
Average Molecular Weight 78.133
Monoisotopic Molecular Weight 78.013935504
IUPAC Name methanesulfinylmethane
Traditional IUPAC Name dimethyl sulfoxide
CAS Registry Number 67-68-5
SMILES CS(C)=O
InChI Identifier InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
InChI Key IAZDPXIOMUYVGZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Sulfoxides
Sub Class N/A
Other Descriptors
  • a small molecule(Cyc)
  • sulfoxide(ChEBI)
Substituents
  • N/A
Direct Parent Sulfoxides
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction
  • Osmolyte, enzyme cofactor, signalling
Application Not Available
Cellular locations Not Available
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 18.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000 mg/mL Not Available
LogP -1.35 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP -1.09 ALOGPS
LogP -1.4 ChemAxon
LogS -0.08 ALOGPS
pKa (strongest basic) -6.2 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 17.07 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 20.73 ChemAxon
Polarizability 7.91 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified
0 - 1.0 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01093 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000764
KNApSAcK ID Not Available
Chemspider ID 659 Link_out
KEGG Compound ID C11143 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Dimethyl sulfoxide Link_out
NuGOwiki Link HMDB02151 Link_out
Metagene Link HMDB02151 Link_out
METLIN ID 3985 Link_out
PubChem Compound 679 Link_out
PDB ID DMS Link_out
ChEBI ID 28262 Link_out
References
Synthesis Reference Goeb, Andre. Dimethyl sulfoxide. Ger. Offen. (1976), 12 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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. Pubmed: 15996001 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA