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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-11 02:12:04 UTC

Update Date

2023-02-21 17:30:37 UTC

HMDB ID

HMDB0061939

Secondary Accession Numbers

HMDB61939

Metabolite Identification

Common Name

Methyl-N,N-diethylthiocarbamate

Description

Methyl-N,N-diethylthiocarbamate belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H). Methyl-N,N-diethylthiocarbamate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl-N,N-diethylthiocarbamic acid	Generator

Chemical Formula

C₆H₁₃NOS₂

Average Molecular Weight

179.304

Monoisotopic Molecular Weight

179.043855423

IUPAC Name

N,N-diethyl-1-methanesulfinylmethanethioamide

Traditional Name

N,N-diethyl-1-methanesulfinylmethanethioamide

CAS Registry Number

Not Available

SMILES

CCN(CC)C(=S)S(C)=O

InChI Identifier

InChI=1S/C6H13NOS2/c1-4-7(5-2)6(9)10(3)8/h4-5H2,1-3H3

InChI Key

VQRMNXBTDRJEKI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

Alternative Parents

Substituents

Sulfoxide
Sulfinyl compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.06 g/L	ALOGPS
logP	1.19	ALOGPS
logP	0.53	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.27 m³·mol⁻¹	ChemAxon
Polarizability	18.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.656	31661259
DarkChem	[M-H]-	136.01	31661259
DeepCCS	[M+H]+	135.191	30932474
DeepCCS	[M-H]-	132.087	30932474
DeepCCS	[M-2H]-	169.12	30932474
DeepCCS	[M+Na]+	144.059	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	135.5	32859911
AllCCS	[M+NH4]+	142.7	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	141.2	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl-N,N-diethylthiocarbamate	CCN(CC)C(=S)S(C)=O	2087.5	Standard polar	33892256
Methyl-N,N-diethylthiocarbamate	CCN(CC)C(=S)S(C)=O	1402.1	Standard non polar	33892256
Methyl-N,N-diethylthiocarbamate	CCN(CC)C(=S)S(C)=O	1558.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl-N,N-diethylthiocarbamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00p0-9400000000-bc1e8e6907f8201f08c4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl-N,N-diethylthiocarbamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 10V, Positive-QTOF	splash10-001i-1900000000-c33b6d5e13b3f076e335	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 20V, Positive-QTOF	splash10-0002-5900000000-3552957beac9edc2efb0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 40V, Positive-QTOF	splash10-05vo-9200000000-f789a9874dc443b6e719	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 10V, Negative-QTOF	splash10-01t9-0900000000-3a2a426a1612a4ea53aa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 20V, Negative-QTOF	splash10-03di-9400000000-2e3c9cda1dca42c5cc9c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 40V, Negative-QTOF	splash10-014u-9300000000-50fb922dec4adf241d46	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 10V, Positive-QTOF	splash10-0159-0900000000-3bb38af0aa83fd90786b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 20V, Positive-QTOF	splash10-014i-3900000000-20baac3cf860195df084	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 40V, Positive-QTOF	splash10-0abc-9000000000-9dc6ea2d95010a577202	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 10V, Negative-QTOF	splash10-03di-9000000000-be513caa85dc087265b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 20V, Negative-QTOF	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl-N,N-diethylthiocarbamate 40V, Negative-QTOF	splash10-01ox-9000000000-67e9dd643e44ede529e4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10197943

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mays DC, Nelson AN, Fauq AH, Shriver ZH, Veverka KA, Naylor S, Lipsky JJ: S-methyl N,N-diethylthiocarbamate sulfone, a potential metabolite of disulfiram and potent inhibitor of low Km mitochondrial aldehyde dehydrogenase. Biochem Pharmacol. 1995 Mar 1;49(5):693-700. [PubMed:7887984 ]
Mays DC, Nelson AN, Lam-Holt J, Fauq AH, Lipsky JJ: S-methyl-N,N-diethylthiocarbamate sulfoxide and S-methyl-N,N-diethylthiocarbamate sulfone, two candidates for the active metabolite of disulfiram. Alcohol Clin Exp Res. 1996 May;20(3):595-600. [PubMed:8727261 ]
Hu P, Jin L, Baillie TA: Studies on the metabolic activation of disulfiram in rat. Evidence for electrophilic S-oxygenated metabolites as inhibitors of aldehyde dehydrogenase and precursors of urinary N-acetylcysteine conjugates. J Pharmacol Exp Ther. 1997 May;281(2):611-7. [PubMed:9152363 ]
Mays DC, Ortiz-Bermudez P, Lam JP, Tong IH, Fauq AH, Lipsky JJ: Inhibition of recombinant human mitochondrial aldehyde dehydrogenase by two intermediate metabolites of disulfiram. Biochem Pharmacol. 1998 Apr 1;55(7):1099-103. [PubMed:9605433 ]
Erve JC, Jensen ON, Valentine HS, Amarnath V, Valentine WM: Disulfiram generates a stable N,N-diethylcarbamoyl adduct on Cys-125 of rat hemoglobin beta-chains in vivo. Chem Res Toxicol. 2000 Apr;13(4):237-44. [PubMed:10775322 ]
Pike MG, Mays DC, Macomber DW, Lipsky JJ: Metabolism of a disulfiram metabolite, S-methyl N,N-diethyldithiocarbamate, by flavin monooxygenase in human renal microsomes. Drug Metab Dispos. 2001 Feb;29(2):127-32. [PubMed:11159801 ]
Ningaraj NS, Chen W, Schloss JV, Faiman MD, Wu JY: S-methyl-N,N-diethylthiocarbamate sulfoxide elicits neuroprotective effect against N-methyl-D-aspartate receptor-mediated neurotoxicity. J Biomed Sci. 2001 Jan-Feb;8(1):104-13. [PubMed:11173983 ]
Percec V, Barboiu B, Grigoras C, Bera TK: Universal iterative strategy for the divergent synthesis of dendritic macromolecules from conventional monomers by a combination of living radical polymerization and irreversible TERminator multifunctional INItiator (TERMINI). J Am Chem Soc. 2003 May 28;125(21):6503-16. [PubMed:12785791 ]
Loo TW, Bartlett MC, Clarke DM: Disulfiram metabolites permanently inactivate the human multidrug resistance P-glycoprotein. Mol Pharm. 2004 Nov-Dec;1(6):426-33. [PubMed:16028354 ]
Hochreiter J, McCance-Katz EF, Lapham J, Ma Q, Morse GD: Disulfiram metabolite S-methyl-N,N-diethylthiocarbamate quantitation in human plasma with reverse phase ultra performance liquid chromatography and mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 May 15;897:80-4. doi: 10.1016/j.jchromb.2012.03.035. Epub 2012 Apr 1. [PubMed:22534656 ]

Showing metabocard for Methyl-N,N-diethylthiocarbamate (HMDB0061939)

MOL for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

3D MOL for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

3D SDF for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

3D-SDF for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

PDB for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

3D PDB for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

SMILES for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

INCHI for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

Structure for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

3D Structure for HMDB0061939 (Methyl-N,N-diethylthiocarbamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra