Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C2H6O4S |
| Molecular Weight | 126.132 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COS(=O)(=O)OC
InChI
InChIKey=VAYGXNSJCAHWJZ-UHFFFAOYSA-N
InChI=1S/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3
| Molecular Formula | C2H6O4S |
| Molecular Weight | 126.132 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Dimethyl sulfate is a diester of methanol and sulfuric acid. Dimethyl sulfate is commonly used as a reagent for the methylation of phenols, amines, and thiols. Dimethyl sulfate is a potent genotoxic chemical. It can directly alkylate DNA both in vitro and in vivo. It have been shown to induce mutations, chromosomal aberrations, and other genetic alterations in a diversity of organisms. Dimethyl sulfate can cause severe burns to the skin, eyes, and respiratory tract. Systemic effects of dimethyl sulfate include damage to the liver and kidneys.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vivo DNase I-mediated footprinting analysis along the human bradykinin B1 receptor (BDKRB1) gene promoter: evidence for cell-specific regulation. | 2005-07-01 |
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| Matrix-isolation FT-IR spectra and theoretical study of dimethyl sulfate. | 2005-05 |
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| Telomerase limits the extent of base pairing between template RNA and telomeric DNA. | 2005-04 |
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| Structural aspects of RecA-dependent homologous strand exchange involving human telomeric DNA. | 2005-03-29 |
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| The structure of a rigorously conserved RNA element within the SARS virus genome. | 2005-01 |
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| Toward multiplexing the application of solvent accessibility probes for the investigation of RNA three-dimensional structures by electrospray ionization-Fourier transform mass spectrometry. | 2004-11-15 |
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| Upstream stimulatory factors, USF1 and USF2, bind to the human haem oxygenase-1 proximal promoter in vivo and regulate its transcription. | 2004-10-15 |
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| Gelsolin gene silencing involving unusual hypersensitivities to dimethylsulfate and KMnO4 in vivo footprinting on its promoter region. | 2004-10-10 |
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| Interaction of telomestatin with the telomeric single-strand overhang. | 2004-10-01 |
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| Divergence of the mRNA targets for the Ssb proteins of bacteriophages T4 and RB69. | 2004-09-17 |
|
| Architecture of a Diels-Alderase ribozyme with a preformed catalytic pocket. | 2004-09 |
|
| Transient adenoviral N-methylpurine DNA glycosylase overexpression imparts chemotherapeutic sensitivity to human breast cancer cells. | 2004-08 |
|
| Analysis in vitro and in vivo of the transcriptional regulator CrgA of Neisseria meningitidis upon contact with target cells. | 2004-08 |
|
| Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents. | 2004-07-01 |
|
| Secondary structure models of the 3' untranslated regions of diverse R2 RNAs. | 2004-06 |
|
| Potassium permanganate as a probe to map DNA-protein interactions in vivo. | 2004-05-31 |
|
| The human T-cell lymphotropic virus type-I dimerization initiation site forms a hairpin loop, unlike previously characterized retroviral dimerization motifs. | 2004-05-25 |
|
| Top-down characterization of nucleic acids modified by structural probes using high-resolution tandem mass spectrometry and automated data interpretation. | 2004-05-01 |
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| Alterations at the peptidyl transferase centre of the ribosome induced by the synergistic action of the streptogramins dalfopristin and quinupristin. | 2004-04-01 |
|
| RMF inactivates ribosomes by covering the peptidyl transferase centre and entrance of peptide exit tunnel. | 2004-04 |
|
| Comparison of tetracycline and tigecycline binding to ribosomes mapped by dimethylsulphate and drug-directed Fe2+ cleavage of 16S rRNA. | 2004-04 |
|
| Steroid hormones induce bcl-X gene expression through direct activation of distal promoter P4. | 2004-03-12 |
|
| Ff gene 5 single-stranded DNA-binding protein assembles on nucleotides constrained by a DNA hairpin. | 2004-03-09 |
|
| Escherichia coli prereplication complex assembly is regulated by dynamic interplay among Fis, IHF and DnaA. | 2004-03 |
|
| Dimethyl sulphate; a hidden problem in occupational medicine. | 2004-01 |
|
| Elimination of oxidative degradation during the per-O-methylation of carbohydrates. | 2003-12-31 |
|
| Charge transport in DNA duplex/quadruplex conjugates. | 2003-12-09 |
|
| Sequence specificity of DNA alkylation by the antitumor natural product leinamycin. | 2003-12 |
|
| Binding of zinc finger protein transcription factor IIIA to its cognate DNA sequence with single UV photoproducts at specific sites and its effect on DNA repair. | 2003-11-14 |
|
| Transcriptional regulation of CHI3L1, a marker gene for late stages of macrophage differentiation. | 2003-11-07 |
|
| Structural organization of a viral IRES depends on the integrity of the GNRA motif. | 2003-11 |
|
| Synthesis and antiprotozoal activity of aza-analogues of furamidine. | 2003-10-23 |
|
| Tetrahedranyllithium: synthesis, characterization, and reactivity. | 2003-10-22 |
|
| Phase-vanishing methodology for efficient bromination, alkylation, epoxidation, and oxidation reactions of organic substrates. | 2003-10-16 |
|
| Transmetalation as a route to novel styryllithium reagents. | 2003-09-18 |
|
| Base excision repair deficiency caused by polymerase beta haploinsufficiency: accelerated DNA damage and increased mutational response to carcinogens. | 2003-09-15 |
|
| Translesion replication in cisplatin-treated xeroderma pigmentosum variant cells is also caffeine-sensitive: features of the error-prone DNA polymerase(s) involved in UV-mutagenesis. | 2003-08-12 |
|
| New pyrazolium-carboxylates as structural analogues of the pseudo-cross-conjugated betainic alkaloid nigellicine. | 2003-07-25 |
|
| Direct probing of RNA structures and RNA-protein interactions in the HIV-1 packaging signal by chemical modification and electrospray ionization fourier transform mass spectrometry. | 2003-07-04 |
|
| Operation Castle Cascade: managing multiple casualties from a simulated chemical weapons attack. | 2003-05 |
|
| Immobilization of thermolysin to polyamide nonwoven materials. | 2003-04-20 |
|
| Caloric restriction promotes genomic stability by induction of base excision repair and reversal of its age-related decline. | 2003-03-01 |
|
| Module-specific regulation of the beta-phaseolin promoter during embryogenesis. | 2003-03 |
|
| Erythromycin, roxithromycin, and clarithromycin: use of slow-binding kinetics to compare their in vitro interaction with a bacterial ribosomal complex active in peptide bond formation. | 2003-03 |
|
| Mechanism of Tet(O)-mediated tetracycline resistance. | 2003-02-17 |
|
| Differential helix stabilities and sites pre-organized for tertiary interactions revealed by monitoring local nucleotide flexibility in the bI5 group I intron RNA. | 2003-02-04 |
|
| An efficient and practical N-methylation of amino acid derivatives. | 2003-01-23 |
|
| Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen. | 2003-01-10 |
|
| Synthesis and in vitro and in vivo evaluation of [11C]methyl-BIII277CL for imaging the PCP-binding site of the NMDA receptor by pet. | 2002-12-31 |
|
| Dimethyl sulfate. | 2002 |
Patents
Sample Use Guides
A single dose of dimethyl sulfate giving an initial concentration of 400 uM raised the levels of nuclear monomeric and polymeric (ADPribose) residues within 20 min to 12- and 21-fold higher values,
respectively, as compared to the low basal amounts detected in untreated control cells.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:37:48 GMT 2025
by
admin
on
Mon Mar 31 20:37:48 GMT 2025
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| Record UNII |
JW5CW40Z50
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C45190
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C44377
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932
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DIMETHYL SULFATE
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6497
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C007482
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2205404
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SUB31758
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77-78-1
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59050
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m4550
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