Dimethyl slifoxide
Dimethyl slifoxide (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 slifoxide 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 usefli 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 particliarly 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 patients own hematopoietic stem cell. Dimethyl slifoxide is a by-product of wood pliping. 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 particliar 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 slifoxonium ion which can be reacted with sodium hydride to form a slifur ylide. The methyl groups of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the reslitant anions by the slifoxide group.
Structure for HMDB02151 (Dimethyl slifoxide)
C2H6OS
78.133
78.013935504
methaneslifinylmethane
dimethyl slifoxide
67-68-5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
This compound belongs to the class of organic compounds known as slifoxides. These are compounds containing a slifoxide functional group, with the structure RS(=O)R (R,R not H).
Organic compounds
Organoslifur compounds
Slifoxides
Not Available
Slifoxides
Aliphatic acyclic compounds
Detected and Quantified
Not Available
Not Available
Liquid
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-004i-9000000000-c8f7a9f09c8bb456283cView in MoNA
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-004i-9000000000-d8d98568ae59afba65e6View in MoNA
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-03di-9000000000-e0a36c290f004f302f0bView in MoNA
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-004i-9000000000-89687ba96456a97fb486View in MoNA
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-01t9-9000000000-04ddc1322b21e4817d57View in MoNA
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4i-9000000000-d90c2fed7aad139b406cView in MoNA
Mass Spectrum (Electron Ionization)splash10-03fr-9000000000-1db858034b22d1646592View in MoNA
1H NMR SpectrumNot Available
13C NMR SpectrumNot Available
Not Available
Not Available
Not Available
Normal
Not Available
None
None
DB01093
Not Available
Not Available
Not Available
FDB000764
Not Available
659
C11143
Not Available
Not Available
Dimethyl slifoxide
HMDB02151
HMDB02151
3985
679
DMS
28262
- 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 ]
Enzymes
- General function:
- Involved in monooxygenase activity
- Specific function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular weight:
- 57255.585
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
- General function:
- Involved in monooxygenase activity
- Specific function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular weight:
- 55944.565
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
- General function:
- Involved in monooxygenase activity
- Specific function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular weight:
- 55768.94
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]