Evaluation of the Long-Term Storage Stability of the Cyanide Antidote: Dimethyl Trisulfide and Degradation Product Identification

Abstract

This study reports the long-term storage stability of a formulation of the cyanide (CN) antidote dimethyl trisulfide (DMTS). The F3-formulated DMTS was stored in glass ampules at 4, 22, and 37 °C. Over a period of one year, nine ampules ( n = 3 at each temperature) were analyzed by high-performance liquid chromatography (HPLC)–UV/vis at daily time intervals in the first week, weekly time intervals in the first month, and monthly thereafter for a period of one year to determine the DMTS content. No measurable loss of DMTS was found at 4 and 22 °C, and good stability was noted up to five months for samples stored at 37 °C. At 37 °C, a 10% (M/M) decrease of DMTS was discovered at the sixth month and only 30% (M/M) of DMTS remained by the end of the study; discoloration of the formulation and the growth of new peaks in the HPLC chromatogram were also observed. To identify the unknown peaks at 37 °C, controlled oxidation studies were performed on DMTS using two strong oxidizing agents: meta -chloroperoxybenzoic acid ( m CPBA) and hydrogen peroxide (H 2 O 2 ). Dimethyl tetrasulfide and dimethyl pentasulfide were observed as products using both of the oxidizing agents. Dimethyl disulfide was also observed as a product of degradation, which was further oxidized to S -methyl methanethiosulfonate only when m CPBA was used. HPLC–UV/vis and gas chromatography–mass spectrometry/solid phase microextraction analysis revealed good agreement between the degradation products of the stability study at 37 °C and those of disproportionation reactions. Furthermore, at 4 and 22 °C, chromatograms were remarkably stable over the one-year study period, indicating that the F3-formulated DMTS shows excellent long-term storage stability at T ≤ 22 °C.

Sulfur-Containing Compounds: Natural Potential Catalyst for the Isomerization of Phytofluene, Phytoene and Lycopene in Tomato Pulp

“…This may be related to the disproportionate reaction of dialkyl polysulfides at high temperatures. For instance, disproportionation/degradation of DMTS could form DMDS [ 36 ], which can further enhance the isomerization reaction.…”

Effect of Maillard Reaction Products Derived from Cysteine on the Formation of Dimethyl Disulfide and Dimethyl Trisulfide during Storage

“…MeSH has been reported to undergo an oxidation reaction that results in DMDS and DMTS . Besides, the disproportionation of DMDS might provide a guarantee for the development of DMTS . Subsequently, the PLSR model was further established using reducing power, DPPH radical-scavenging activity, and 2-methyl-3-(methyldisulfanyl)­furan concentrations as the X variable and DMDS and DMTS concentrations as the Y variable to evaluate factors affecting the formation of DMDS and DMTS.…”

Stabilization Effect of Potato Starch on Characteristic Flavor Compounds in Onion Sauce

“…[25,26] Nevertheless, DT is thermally unstable and can be degraded to form dimethyl tetrasulfide and dimethyl disulfide at 37 °C. [27] Allyl methyl disulfide could form through thiosulfinate degradation due to the unstability of thiosulfinates. [28] In contrast, other sulfides might decompose, recombine, or volatilize, leading to their loss during storage.…”