13256-22-9

Usage

Uses

Given the provided materials, N-Nitrososarcosine is primarily described as a carcinogenic compound. Due to its carcinogenic properties, it is not recommended for use in any industry or application where it may come into contact with humans or the environment. The primary use of N-Nitrososarcosine is for research purposes, where it can be studied to understand its effects on biological systems and potentially contribute to the development of cancer prevention strategies or treatments.
Used in Research Applications:
N-Nitrososarcosine is used as a research compound for studying its carcinogenic properties and understanding its effects on biological systems. This knowledge can be applied to develop strategies for cancer prevention and treatment.
It is crucial to handle N-Nitrososarcosine with extreme caution and under controlled laboratory conditions due to its carcinogenic nature. Any potential applications outside of research should be thoroughly evaluated for safety and potential risks before implementation.

Safety Profile

Confirmed carcinogen with experimental tumorigenic data. Mildly toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.See also N-NITROSO COMPOUNDS.

Carcinogenicity

N-Nitrososarcosine is reasonably anticipated to b e a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

InChI:InChI=1/C3H6N2O3/c1-5(4-8)2-3(6)7/h2H2,1H3,(H,6,7)

Upstream product

• 107-97-1 sarcosine 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 1118-68-9 dimethylaminoacetic acid 
• 67809-83-0 S-nitroso-N-acetylpenicillamine 
• 10242-53-2 2--acetamid 

Downstream Products

• 20661-60-3 N-methyl-N-nitroglycine 
• 51938-19-3 C₄H₈N₂O₃ 
• 25044-59-1 N-Nitroso-sarkosin-<4-nitro-phenylester> 
• 53261-86-2 C₁₃H₁₆N₄O₆ 
• 6939-12-4 N-methylsydnone 
• 25044-54-6 Nitroso-sarkosin-2,4,6-trimethylbenzylester; NO-Sar-OTMB 
• 107-97-1 sarcosine 
• 25044-53-5 N-Nitroso-sarkosin-<4-brom-phenacylester> 

Relevant academic research and scientific papers

NITROSATION REAGENTS AND METHODS

Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15N isotope.

Versatile new reagent for nitrosation under mild conditions

Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

Sydnone Cycloaddition Route to Pyrazole-Based Analogs of Combretastatin A4

The combretastatins are an important class of tubulin-binding agents. Of this family, a number of compounds are potent tumor vascular disrupting agents (VDAs) and have shown promise in the clinic for cancer therapy. We have developed a modular synthetic r

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl

Zwitterionic and mesoionic liquids: Molecular aggregation in 3-methylsydnone

Ionic liquids are green solvents with interesting properties: displaying low melting points and high boiling points. They offer a new approach applicable in many instances. Nevertheless, the presence of free ions can be a matter in some cases, e.g. for the study of nucleophilic reactions, in electrochemistry, and in each situation where there is a competition between counter ions, as in micellization of ionic surfactants. Neutral compounds having formal unit electrical charges of opposite sign, and the same physical properties than ionic liquids would be a nice alternative to these latter solvents. There are two classes of chemical compounds having these characteristics: zwitterionic liquids (with no uncharged canonical representation) and mesoionic liquids (in which the negative and the positive charges are delocalized). In that last class we have chosen to work with 3-methylsydnone in order to examine, in this aprotic solvent, if it was possible to observe aggregation of surfactants in the same manner as in water. With all kinds of surfactants studied (ionic, zwitterionic and mesoionic) we have been able to demonstrate the formation of direct micelles: hydrogen bonding is thus not mandatory for molecular aggregation. Comparison of the behavior in water and in formamide showed that solvophobic interactions were qualitatively comparable but with a lower intensity.

Reactivity of nitrogen nucleophiles towards S-nitrosopenicillamine

We report the results of a kinetic study of the reactions of a number of nitrogen nucleophiles with the nitrosothiol S-nitrosopenicillamine (SPEN). The range of nucleophiles includes primary, secondary and tertiary aliphatic amines, together with hydrazine, hydroxylamine, azide ion, ammonia, semicarbazide, thiomorpholine and S-methylcysteine. Secondary amines form N-nitrosamines quantitatively. As expected, reaction occurs via the free base forms of the nucleophiles and consequently most of the reactions take place readily only at relatively high pH. Experiments were carried out with [nucleophile] ? [RSNO], and for many reactions, plots of the first order rate constant vs. [nucleophile] were linear. For ammonia and the primary amines, however, this plot tended to level off at high [nucleophile] and an explanation is offered involving the reversible formation of an inactive RSNO-amine complex, for which there is spectral evidence, in parallel with the main reaction. For the secondary amines there is a reasonably good Broensted plot with a β value of ～0.2. The much greater reactivities of S-methylcysteine and thiomorpholine, compared to those of primary amines and morpholine respectively are consistent with initial attack at the sulfur atom, followed by an internal rearrangement. Over the whole range of nucleophiles studied there is a reasonable correlation with the Ritchie N+ parameter, and not with the Pearson n scale. Comparisons are made with the corresponding reactions of alkyl nitrites and N-methyl-N-nitrosotoluene-p-sulfonamide (MNTS).

Synthesis and reactions of 9,10-diazatetracyclo-[6.3.0.0.4,110.5.9]undecanes

The tandem 1,3-dipolar cycloaddition between sydnones and 1,5-cyclooctadiene provides 9,10-diazatetracyclo[6.3.0.0.4,110.5,9]undecanes (the Weintraub reaction) in modest to good yields.

Kinetic Studies on the Influence of Micellar Aggregates upon the Hydrolysis and Transnitrosation Reactions of N-methyl-N-nitrosotoluene-p-sulphonamide

The basic hydrolysis of N-methyl-N-nitrosotoluene-p-sulphonamide and its transnitrosation reaction with secondary amines (sarcosine and dimethylamine) have been studied in the presence of cationic, anionic, and non-ionic micelles.The results show that the electric charge of the nucleophile is essential for the understanding of the micellar effects, which can be quantitatively rationalized on the basis of the pseudophase kinetic model.Thus the reaction with negatively charged nucleophiles is inhibited by both anionic and non-ionic surfactants, whereas cationic micelles increase the reaction rate, which passes through a maximum.The reaction between the substrate and a neutral nucleophile is, however, inhibited by all three classes of surfactant.