Showing Compound Card for Dimethyltrisulfide (CDB005662)

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Record Information
Version1.0
Created at2020-04-27 16:43:10 UTC
Updated at2021-01-04 18:59:22 UTC
CannabisDB IDCDB005662
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDimethyltrisulfide
DescriptionDimethyl trisulfide, also known as DMTS, belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl). Dimethyl trisulfide is a clear, yellowish flammable liquid with a foul odor (at high levels), which is detectable at levels as low as 1 part per trillion. At lower doses (<0.1%) it has a cooked onion, meaty or savory aroma with a sulfurous, vegetable or savory taste. Dimethyl trisulfide is found in a number different foods, such as kohlrabis, asparagus, cheese, cooked chicken, coffee, cocoa, garlic, cow’s milk, sauerkraut, shrimp, tomatoes, white wine, soft-necked garlics, broccoli, shiitakes, garden onions, mushrooms, and nuts. This could make dimethyl trisulfide a potential biomarker for the consumption of these foods. Dimethyl trisulfide has also been found in volatiles emitted from cooked onion, leek and other allium species, from broccoli and cabbage, as well as from Limburger cheese. DMTS is associated with the unpalatable aroma of aged beer and stale Japanese sake. It is a decomposition product from bacterial decomposition, including the early stages of human decomposition, and is a major attractant for blowflies looking for hosts. Dimethyl trisulfide along with dimethyl sulfide and dimethyl disulfide have been confirmed as volatile compounds given off by the fly-attracting plant known as dead-horse arum (Helicodiceros muscivorus). These flies are attracted to the odor of fetid meat and help pollinate this plant. DMTS contributes to the foul odor given off by the fungus Phallus impudicus, also known as the common stinkhorn. DMTS causes the characteristic malodorous smell of a fungating lesion, e.g., from cancer wounds (PMID: 19734656 ), and contributes to the odor of human feces (PMID 3678751 ). Dimethyl trisulfide has been found to be an effective cyanide antidote in a rodent model for cyanide poisoning both against subcutaneous potassium cyanide and inhaled hydrogen cyanide, converting cyanide to much less toxic thiocyanate (PMID: 28922956 ). It is suggested that dimethyl trisulfide can be used in a mass casualty cyanide exposure setting. Dimethyl trisulfide is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DMTSKegg
Dimethyl trisulphideGenerator
(Methyltrisulphanyl)methaneGenerator, HMDB
(Methyldisulfanyl)methaneHMDB
(methyldithio)MethaneHMDB
1,3-Dimethyltrisulfane (acd/name 4.0)HMDB
2,3,4-TrithiapentaneHMDB
2,3-DithiabutaneHMDB
CH3SSSCH3HMDB
Dimethyl disulfideHMDB
Dimethyl disulphideHMDB
Dimethyl trisufideHMDB
DimethyldisulfideHMDB
Disulfide dimethylHMDB
DMDSHMDB
Methyl disulfideHMDB
Methyl trisulfideHMDB
MethyldisulfanylmethaneHMDB
MethyldisulfideHMDB
MethyldithiomethaneHMDB
Sulfa-hitechHMDB
Sulfa-hitech 0382HMDB
Trisulfide, dimethylHMDB
DimethyltrisulphideGenerator
Chemical FormulaC2H6S3
Average Molecular Weight126.26
Monoisotopic Molecular Weight125.9632
IUPAC Namedimethyltrisulfane
Traditional Namedimethyl trisulfide
CAS Registry Number3658-80-8
SMILES
CSSSC
InChI Identifier
InChI=1S/C2H6S3/c1-3-5-4-2/h1-2H3
InChI KeyYWHLKYXPLRWGSE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassOrganic trisulfides
Sub ClassNot Available
Direct ParentOrganic trisulfides
Alternative Parents
Substituents
  • Organic trisulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-85 °CNot Available
Boiling Point170 °CWikipedia
Water SolubilityNot AvailableNot Available
logP1.94Extrapolated
Predicted Properties
PropertyValueSource
logP1.26ALOGPS
logP1.94ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.9 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004j-9400000000-4e5c63061823b6b4c4cc2015-03-01View Spectrum
GC-MSDimethyltrisulfide, non-derivatized, GC-MS Spectrumsplash10-004i-8900000000-51e17f5b584d2fdfd191Spectrum
GC-MSDimethyltrisulfide, non-derivatized, GC-MS Spectrumsplash10-004i-8900000000-51e17f5b584d2fdfd191Spectrum
Predicted GC-MSDimethyltrisulfide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9300000000-037f42abb3957558d4e7Spectrum
Predicted GC-MSDimethyltrisulfide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDimethyltrisulfide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-61231e5b160f22dd1c562016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-9800000000-eb790025dc00755388c62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-f4c5d73c87f08fa91de02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-5e8315171f233d541f392016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0096-9400000000-793416ef4f3539a799062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-48ed295af11468ac4ccb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9400000000-e613f769a7029426976e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-387982f94fea0aab542b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-c6b3a8b5e85e7e221ef62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-46805203bee4610642252021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9000000000-40243fb3cada14f287f82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1d58e6810a052e42af362021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0013780
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012458
KNApSAcK IDC00001246
Chemspider ID18219
KEGG Compound IDC08372
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl trisulfide
METLIN IDNot Available
PubChem Compound19310
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Shirasu M, Nagai S, Hayashi R, Ochiai A, Touhara K: Dimethyl trisulfide as a characteristic odor associated with fungating cancer wounds. Biosci Biotechnol Biochem. 2009 Sep;73(9):2117-20. doi: 10.1271/bbb.90229. Epub 2009 Sep 7. [PubMed:19734656 ]
  2. Moore JG, Jessop LD, Osborne DN: Gas-chromatographic and mass-spectrometric analysis of the odor of human feces. Gastroenterology. 1987 Dec;93(6):1321-9. doi: 10.1016/0016-5085(87)90262-9. [PubMed:3678751 ]
  3. DeLeon SM, Downey JD, Hildenberger DM, Rhoomes MO, Booker L, Rockwood GA, Basi KA: DMTS is an effective treatment in both inhalation and injection models for cyanide poisoning using unanesthetized mice. Clin Toxicol (Phila). 2018 May;56(5):332-341. doi: 10.1080/15563650.2017.1376749. Epub 2017 Sep 19. [PubMed:28922956 ]