18342-66-0

Basic information

• Product Name: N-Succinimidyl-N-methylcarbamate
• Synonyms: 2,5-PYRROLIDINEDIONE, 1-[[(METHYLAMINO)CARBONYL]OXY]-;N-SUCCINIMDYL-N-METHYLCARBAMATE;N-SUCCINIMIDYL-N-METHYLCARBAMATE;N-Succinimidyl-N-methylcarbama;methyl isocyanate substitute;Methyl isocyanate substitute, MIC substitute;2,5-dioxopyrrolidin-1-yl MethylcarbaMate;SuO-NM
• CAS NO: 18342-66-0
• Molecular Formula: C₆H₈N₂O₄
• Molecular Weight: 172.14
• Product Categories: Medical Intermediates;Norbornene Derivatives
• Mol File: 18342-66-0.mol

Chemical Properties

• Melting Point: 148-153 °C
• Appearance: /Solid
• Density: 1.416 g/cm³
• Refractive Index: 1.527
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane (Slightly), DMSO (Slightly)
• PKA: 11.00±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1531863
• CAS DataBase Reference: N-Succinimidyl-N-methylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Succinimidyl-N-methylcarbamate(18342-66-0)
• EPA Substance Registry System: N-Succinimidyl-N-methylcarbamate(18342-66-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 18342-66-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Succinimidyl-N-methylcarbamate is used as a reagent for the synthesis of Argifin, a natural product chitinase inhibitor with chemotherapeutic potential. It plays a crucial role in the development of this compound, which may have applications in cancer treatment.
Used in the Preparation of A616300:
N-Succinimidyl-N-methylcarbamate is also used as a reagent in the preparation of 5-Amino-N1-methyl-1H-imidazole-1,4-dicarboxamide (A616300), a metabolite of Temozolomide (T017775). Temozolomide is an imidazotetrazine alkylating agent and antineoplastic, which means it has cancer-fighting properties. The use of N-Succinimidyl-N-methylcarbamate in the synthesis of A616300 contributes to the development of this potent chemotherapeutic agent.

InChI:InChI=1/C6H8N2O4/c1-7-6(11)12-8-4(9)2-3-5(8)10/h2-3H2,1H3,(H,7,11)

Upstream product

• 74124-79-1 di(succinimido) carbonate 
• 74-89-5 methylamine 
• 15149-73-2 2,5-dioxopyrrolidin-1-yl carbonochloridate 
• 593-51-1 methylamine hydrochloride 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 624-83-9 methyl isocyanate 

Downstream Products

• 80354-48-9 N-methyl-N-nitrosocarbamic acid N'-hydroxysuccinimide ester 
• 243975-37-3 cyclo(N^w-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl) 
• 903556-24-1 C₁₄H₂₁N₃O₃ 
• 903556-18-3 C₁₄H₂₁N₃O₃ 
• 188612-53-5 5-amino-N₁-methyl-1H-imidazole-1,4-dicarboxamide 
• 1401110-65-3 C₃₇H₃₈N₆O₇ 
• 38126-73-7 S-(N-methylcarbamoyl)glutathione 

Relevant articles and documents

Synthesis and in vitro antitumor activity of novel 2-alkyl-5- methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine.

Preparation and screening against acetylcholinesterase of a non-peptide "indexed" combinatorial library

A combinatorial library composed from nine alcohols and six isocyanates to formally generate 54 carbamates has been designed prepared, and screened against acetylcholinesterase from the electric eel. In order to deduce the most active member of the library, it was prepared as 15 sublibraries in which one of the reacting components was fixed and the other reactants were used as an equimolar mixture. The product mixtures were tested and their activities used as "indices" to the rows or columns of a two-dimensional matrix reflecting the activities of individual carbamates. A number of carbamates in the most active row and column were synthesized and assayed, demonstrating that the most active cell in the matrix could be identified by the sublibrary synthesis procedure. Other methods for generating large libraries of molecules for biological screening that have recently been developed have relied on a covalent attachment between library members and a label to identify the active components. Indexed libraries otter the advantage that they can be prepared from any class of compounds composed from multiple subunits and that any type of assay (binding, enzyme inhibition, agonism/antagonism, cell-based, or even whole organism assays for biological activity) can be used because all compounds are generated in a free form.

A convenient method for the synthesis of activated N-methylcarbamates

An investigation of methods to efficiently prepare activated N-methylcarbamates is reported. N-(Methylcarbamoyloxy)succinimide (3a), aryl N-methylcarbamates 3b-d and 2,2,2-trifluoro-1-(trifluoromethyl)ethyl N-methylcarbamate (3e) have been prepared in 70-80% yields from the corresponding chloroformates 5a-e, which were prepared as crystalline solids by the condensation of trichloromethylchloroformate (1) or bis(trichloromethyl)carbonate (2) with hydroxy compounds 4a-e in high yields.

Convenient Methods for Syntheses of Active Carbamates, Ureas and Nitrosoureas Using N,N'-disuccinimido Carbonate (DSC)

The reaction of DSC and amino compounds afforded the corresponding carbamates which were able to be converted into ureas and nitrosoureas.

Activated N-Nitrosocarbamates for Regioselective Synthesis of N-Nitrosoureas

A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed.N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas.As an interesting example, N,N'-biscystamine, a new attractive oncostatic derivative, has been prepared.The cytotoxic activity of these various compounds were tested on L1210 leukemia.

Dicarboximido-N-phenylsubstituted carbamates and derivatives

The Dicarboximido-N-Monosubstituted Carbamates of this invention are pesticidally active and particularly useful as herbicides.