140703-15-7

Basic information

• Product Name: S-Methyl-N,N-diethylthiocarbamate Sulfoxide
• Synonyms: S-Methyl-N,N-diethylthiocarbamoyl Sulfoxide;Methyl Diethylthiocarbamate Sulfoxide;N,N-Diethyl-1-(methylsulfinyl)-formamide;S-methyl N,N-diethylthiolcarbamate sulfoxide;S-METHYLN,N-DIETHYLTHIOLCARBAMATESULPHOXIDE;DETC MeSO
• CAS NO: 140703-15-7
• Molecular Formula: C6H13NO2S
• Molecular Weight: 163.24
• Product Categories: All Inhibitors;Inhibitors;Sulfur & Selenium Compounds
• Mol File: 140703-15-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 255.4°Cat760mmHg
• Flash Point: 108.3°C
• Appearance: /
• Density: 1.154g/cm³
• Vapor Pressure: 0.0163mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Stability: Light and Temperature Sensitive
• CAS DataBase Reference: S-Methyl-N,N-diethylthiocarbamate Sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: S-Methyl-N,N-diethylthiocarbamate Sulfoxide(140703-15-7)
• EPA Substance Registry System: S-Methyl-N,N-diethylthiocarbamate Sulfoxide(140703-15-7)

Safety Data

• Hazardous Substances Data: 140703-15-7(Hazardous Substances Data)

Usage

Description

S-Methyl-N,N-diethylthiocarbamate Sulfoxide, also known as Disulfiram metabolite, is an oxygenated compound derived from Disulfiram (Antabuse). It is characterized by its pale yellow oil appearance and is known for its ability to inactivate liver mitochondrial aldehyde dehydrogenase (ALDH) in vitro.

Uses

Used in Pharmaceutical Industry:
S-Methyl-N,N-diethylthiocarbamate Sulfoxide is used as a research compound for aldehyde dehydrogenase (ALDH) related studies. It is particularly valuable in the development and understanding of treatments for alcoholism and other conditions where ALDH plays a significant role.
Used in Biomedical Research:
S-Methyl-N,N-diethylthiocarbamate Sulfoxide is used as a research tool in biomedical research to study the function and regulation of aldehyde dehydrogenase (ALDH) enzymes. S-Methyl-N,N-diethylthiocarbamate Sulfoxide aids in investigating the role of ALDH in various biological processes and its potential as a therapeutic target for certain diseases.
Used in Chemical Synthesis:
S-Methyl-N,N-diethylthiocarbamate Sulfoxide can be used as an intermediate in the synthesis of other related compounds, potentially leading to the development of new pharmaceuticals or chemical products with specific applications in various industries.

InChI:InChI=1/C6H13NO2S/c1-4-7(5-2)6(8)10(3)9/h4-5H2,1-3H3

Upstream product

• 37174-63-3 S-Methyl N,N-diethylthiocarbamate 

Downstream Products

• 155514-79-7 S-methyl N,N-diethylthiolcarbamate sulfone 
• 157723-51-8 S-(N,N-diethylcarbamoyl)glutathione 

Relevant articles and documents

S-Methyl N,N-Diethylthiocarbamate Sulfone, a Potential Metabolite of Disulfiram and Potent Inhibitor of Low Km Mitochondrial Aldehyde Dehydrogenase

Disulfiram inhibits hepatic aldehyde dehydrogenase (ALDH) causing an accumulation of acetaldehyde after ethanol ingestion. It is thought that disulfiram is too short-lived in vivo to directly inhibit ALDH, but instead is biotransformed to reactive metabolites that inhibit the enzyme. S-Methyl N,N-diethylthiocarbamate (MeDTC) sulfoxide has been identified in the blood of animals given disulfiram and is a potent inhibitor of ALDH (Hart and Faiman, Biochem Pharmacol 46: 2285-2290, 1993). MeDTC sulfone is a logical metabolite of MeDTC sulfoxide. Therefore, we investigated the effects of MeDTC sulfone on the activity of rat hepatic low Km mitochondrial ALDH, the major enzyme in the metabolism of acetaldehyde. MeDTC sulfone inhibited the low Km mitochondrial ALDH in vitro with an IC50 of 0.42 +/- 0.04 μM (mean +/- SD, N = 5) compared with disulfiram, which had an IC50 of 7.5 +/- 1.2 μM under the same conditions. The inhibition of ALDH by MeDTC sulfone was time dependent. The decline in ALDH activity followed pseudo first-order kinetics with an apparent half-life of 2.1 min at 0.6 μM MeDTC sulfone. Inhibition of ALDH by MeDTC sulfone was apparently irreversible; dilution of the inhibited enzyme did not restore lost activity. The substrate (acetaldehyde, 80 μM) and cofactor (NAD, 0.5 mM) together completely protected ALDH from inhibition by MeDTC sulfone; substrate alone partially protected the enzyme. Addition of either thiol-containing compound glutathione (GSH) or dithiothreitol (DTT) to MeDTC sulfone before incubation with the enzyme increased the IC50 of MeDTC sulfone by 7- to 14-fold. Neither GSH nor DTT could restore lost ALDH activity after exposure of the enzyme to MeDTC sulfone. Results of these studies indicate that MeDTC sulfone, a potential metabolite of disulfiram, is a potent, irreversible inhibitor of low Km mitochondrial ALDH.