Page last updated: 2024-12-05

dimethyl sulfate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

dimethyl sulfate: RN given refers to unlabeled cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dimethyl sulfate : The dimethyl ester of sulfuric acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6497
CHEMBL ID162150
CHEBI ID59050
SCHEMBL ID1249
MeSH IDM0050712

Synonyms (99)

Synonym
dimethoxysulfone
sulfato de dimetilo
dwumetylowy siarczan
dimethylsulfat
methyle (sulfate de)
nsc-56194
dimethyl monosulfate
wln: 1oswo1
dimetilsolfato
sulfate de methyle
methyl sulfate, me2so4
sulfate dimethylique
dimethylester kyseliny sirove
nsc56194
dms (methyl sulfate)
dimethylsulfaat
sulfuric acid, dimethyl ester
inchi=1/c2h6o4s/c1-5-7(3,4)6-2/h1-2h
77-78-1
dimethyl sulfate
dimetilsolfato [italian]
sulfato de dimetilo [spanish]
hsdb 932
brn 0635994
sulfate de dimethyle [french]
methyle (sulfate de) [french]
methyl sulfate (van)
einecs 201-058-1
dimethylsulfate
dimethylsulfaat [dutch]
sulfate dimethylique [french]
dimethylsulfat [czech]
nsc 56194
ai3-52118
rcra waste no. u103
dwumetylowy siarczan [polish]
un1595
rcra waste number u103
dimethyl sulphate
dimethylester kyseliny sirove [czech]
ccris 265
dimethyl sulfate, >=99%
dimethyl sulfate, puriss. p.a., >=99.0% (gc)
dimethyl sulfate, >=99.8%
CHEMBL162150
chebi:59050 ,
sulfuric acid dimethyl ester
AKOS000119929
NCGC00248118-01
NCGC00248118-02
unii-jw5cw40z50
dimethyl sulfate [un1595] [poison]
sulfate de dimethyle
ec 201-058-1
jw5cw40z50 ,
C19177
NCGC00254411-01
NCGC00259581-01
tox21_202032
tox21_300636
cas-77-78-1
dtxsid5024055 ,
dtxcid904055
D0797
me2so4
1216599-58-4
dimethyl sulfate [hsdb]
dimethyl sulfate [mi]
dimethyl sulfate [iarc]
STL264200
BP-21324
SCHEMBL1249
62086-97-9
139443-72-4
98478-67-2
dimethyl-sulfate
dimetylsulphate
(ch3)2so4
dimethlysulfate
dimethylsulfuric acid
dimethylsulphate
dimethyl sulfuric acid
dirnethyl sulfate
dimethysulfate
sulphuric acid dimethyl ester
un 1595
BBL034656
mfcd00008416
dimethyl sulfate, for gc derivatization, >=99.0% (gc)
dimethyl sulfate, purum, >=95.0% (gc)
dimethyl sulfate, saj first grade, >=99.0%
Q413421
VS-12630
dimethyl sulfate (13c2)
AMY40210
E78998
EN300-19226
dms(methyl sulfate)
dimethyl sulfate (iarc)

Research Excerpts

Overview

Dimethyl sulfate (DMS) is an alkylating reagent commonly used in organic syntheses and pharmaceutical manufacturing processes. DMS is carcinogenic to the respiratory tract of rodents.

ExcerptReferenceRelevance
"Dimethyl sulfate (DMS) is a chemical probe that has long been used to detect footprints of DNA-bound proteins in vitro and in vivo."( DMS-Seq for In Vivo Genome-wide Mapping of Protein-DNA Interactions and Nucleosome Centers.
Ito, T; Umeyama, T, 2017
)
1.18
"Dimethyl sulfate (DMS) is an alkylating reagent commonly used in organic syntheses and pharmaceutical manufacturing processes. "( Determination of low ppm levels of dimethyl sulfate in an aqueous soluble API intermediate using liquid-liquid extraction and GC-MS.
Pritts, WA; Wittenberger, S; Zhang, S; Zheng, J, 2009
)
2.07
"Dimethyl sulfate (DMS) is an alkylating agent that is carcinogenic to the respiratory tract of rodents. "( DNA methylation, cell proliferation, and histopathology in rats following repeated inhalation exposure to dimethyl sulfate.
Bogdanffy, MS; Frame, SR; Mathison, BH, 2004
)
1.98
"Dimethyl sulfate (DMS) is a volatile sulfuric acid ester used principally as a methylating agent in a wide variety of industrial applications. "( Interspecies dose extrapolation for inhaled dimethyl sulfate: a PBPK model-based analysis using nasal cavity N7-methylguanine adducts.
Barton, HA; Bogdanffy, MS; Clewell, HJ; Gentry, PR; Sarangapani, R; Teeguarden, JG, 2004
)
2.03

Effects

Dimethyl sulfate has been recently reported to cause RADS and repeated diesel exhaust exposure to cause not-so-sudden IIA in patients who worked in a bus garage. Dimethyl sulfat footprinting has allowed the detection of a protein-DNA interaction within the curved ND2 region.

ExcerptReferenceRelevance
"Dimethyl sulfate has been recently reported to cause RADS and repeated diesel exhaust exposure to cause not-so-sudden IIA in patients who worked in a bus garage."( Irritant-induced asthma.
Labrecque, M, 2012
)
1.1
"Dimethyl sulfate footprinting has allowed the detection of a protein-DNA interaction within the curved ND2 region with contact sites located in both the strands."( In organello footprinting analysis of rat mitochondrial DNA: protein interaction upstream of the Ori-L.
Capaccio, L; Cingolani, G; D'Elia, D; Gadaleta, G, 1997
)
1.02

Toxicity

ExcerptReferenceRelevance
"Escherichia coli can ameliorate the toxic effects of alkylating agents either by preventing DNA alkylation or by repairing DNA alkylation damage."( The Escherichia coli AlkB protein protects human cells against alkylation-induced toxicity.
Carroll, P; Chen, BJ; Samson, L, 1994
)
0.29

Dosage Studied

ExcerptRelevanceReference
" For both compounds, very similar dose-response curves were found for induction of chromatid breaks in the dose range 10-75 mg/kg."( Transplacental genetic and cytogenetic effects of alkylating agents in the mouse. II. Induction of chromosomal aberrations.
Braun, R; Hüttner, E; Schöneich, J, 1986
)
0.27
" Dose-response experiments indicate that the changes in chromatin structure at the enhancer and promoter are graded and mirror the graded induction of Cyp1A1 transcription by dioxin."( Dioxin induces localized, graded changes in chromatin structure: implications for Cyp1A1 gene transcription.
Okino, ST; Whitlock, JP, 1995
)
0.29
" This paper summarizes some of the critical attributes of the hazard identification and dose-response aspects of risk assessments for nasal carcinogens that must be accounted for by risk assessors in order to make informed decisions."( Critical factors in assessing risk from exposure to nasal carcinogens.
Bogdanffy, MS; Harman, AE; Kuykendall, JR; Mathison, BH, 1997
)
0.3
" Their effects on cellular DNMT1 are time and dosage dependent but independent of cell type."( Selective depletion of human DNA-methyltransferase DNMT1 proteins by sulfonate-derived methylating agents.
Chuang, LS; Li, BF; Oh, HK; Tan, EH, 2002
)
0.31
" We substituted dimethyl sulfate (DMS) to create alkylating damage in pCMVluc plasmid DNA and established the damage-repair dose-response curves in both normal and nucleotide excision repair-deficient lymphoblastoid cell lines and in phytohemagglutinin (PHA)-stimulated primary lymphocytes."( A modified host-cell reactivation assay to measure repair of alkylating DNA damage for assessing risk of lung adenocarcinoma.
Guo, Z; Qiao, Y; Shi, Q; Spitz, MR; Wang, L; Wei, Q, 2007
)
0.69
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
alkylating agentHighly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
immunosuppressive agentAn agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
alkyl sulfate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency54.94100.000221.22318,912.5098AID743036
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency54.48270.003041.611522,387.1992AID1159552
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID134111Mean life extension in mice bearing Trypanosoma rhodesiense, after ip administration at a dose of 0.2 mmol/kg1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Methylating agents as trypanocides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (645)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990187 (28.99)18.7374
1990's254 (39.38)18.2507
2000's127 (19.69)29.6817
2010's57 (8.84)24.3611
2020's20 (3.10)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 57.25

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index57.25 (24.57)
Research Supply Index6.51 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index97.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (57.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews13 (1.95%)6.00%
Case Studies11 (1.65%)4.05%
Observational0 (0.00%)0.25%
Other644 (96.41%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]