5146-68-9

Basic information

• Product Name: N-hydroxymethylsuccinimide
• Synonyms: N-hydroxymethylsuccinimide;2,3-Pyrrolidinedione, 1-(hydroxymethyl)- (9ci);2,5-Pyrrolidinedione, 1-(hydroxymethyl)-;Ai3-62022;Brn 0120425;N-Hydroxy-methyl-succinimid;N-Hydroxy-methyl-succinimid [german];1-(hydroxymethyl)-2,5-pyrrolidinedione
• CAS NO: 5146-68-9
• Molecular Formula: C₅H₇NO₃
• Molecular Weight: 129.114
• Mol File: 5146-68-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 66 °C
• Boiling Point: 362.2 °C at 760 mmHg
• Flash Point: 172.8 °C
• Appearance: /
• Density: 1.413 g/cm³
• Vapor Pressure: 1.04E-06mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.66±0.10(Predicted)
• CAS DataBase Reference: N-hydroxymethylsuccinimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxymethylsuccinimide(5146-68-9)
• EPA Substance Registry System: N-hydroxymethylsuccinimide(5146-68-9)

Safety Data

• Hazardous Substances Data: 5146-68-9(Hazardous Substances Data)

Usage

General Description

N-hydroxymethylsuccinimide is a chemical compound commonly used in the field of bioconjugation and protein modification. It acts as a bifunctional crosslinking reagent, enabling the covalent linkage of molecules such as proteins, peptides, and antibodies to other molecules or surfaces. The compound contains a succinimide group which reacts with primary amines in proteins, and a hydroxymethyl group which facilitates the conjugation process. N-hydroxymethylsuccinimide is often utilized in the preparation of antibody-drug conjugates and in the immobilization of proteins onto solid surfaces for various biomedical and research applications. Its versatility and stability make it a valuable tool in bioconjugation chemistry.

InChI:InChI=1/C5H7NO3/c7-3-6-4(8)1-2-5(6)9/h7H,1-3H2

Upstream product

• 123-56-8 Succinimide 
• 50-00-0 formaldehyd 
• 50680-64-3 1-(2-bromomethyl)pyrrolidine-2,5-dione 

Downstream Products

• 134697-08-8 1-(4-Methoxy-phenoxymethyl)-pyrrolidine-2,5-dione 
• 134697-07-7 Succinimidylmethoxybenzene 
• 1026091-18-8 [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester 
• 123-56-8 Succinimide 
• 50-00-0 formaldehyd 
• 54135-60-3 2,2'-methylenebis(cyclohexane-1,3-dione) 
• 51532-41-3 bis(succinimidomethyl) ether 
• 39101-32-1 N-(4,5-dimethoxy-2-nitro-benzyl)-succinimide 

Relevant articles and documents

Synthesis, biological evaluation and pharmacokinetic studies of mefenamic acid - N-Hydroxymethylsuccinimide ester prodrug as safer NSAID

Background: Non steroidal anti-inflammatory drugs are the most widely prescribed drugs to manage pain and inflammatory conditions, but their long term use is associated with gastrointestinal toxicity. Objectives: The study aimed to synthesize an ester-bas

Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde

Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF3SO2NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF3SO2NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.

Cyclic amide derivatives as potential prodrugs II: N- hydroxymethylsuccinimide- / isatin esters of some NSAIDs as prodrugs with an improved therapeutic index

Ester prodrugs of aspirin la, ibuprofen 1b, naproxen 1c and indomethacin 1d were synthesized using N-Hydroxymethylsuccinimide (HMSI) 3 and N- hydroxymethylisatin (HMIS) 4 as promoieties to reduce their gastrointestinal toxicity and improve bioavailability. Additionally, the kinetics of hydrolysis of the synthesized prodrugs 5a-d and 6a-d were studied at 37°C in non-enzymatic simulated gastric fluid (SGF; hydrochloric acid buffer pH = 1.2); 0.02 M phosphate buffer (pH = 7.4); 80% human plasma and 10% rat liver homogenate. The results indicate higher chemical stability of the ester prodrugs in non-enzymatic SGF (t(1/2) ? 6.5-18.6 h) and rapid conversion to the parent drugs in 80% human plasma (t(1/2) ? 11.4-235 min) as well as in 10% rat liver homogenates (t(1/2) ? 12.0-90.0 min). As a general pattern, the HMSI esters 5a-d revealed higher chemical stability than the corresponding HMIS analogues 6a-d. The pH-rate profile of 5c and 6a indicated maximum stability of the former at pH = 1.2-8.0 and of the latter at pH = 1.2-4.0. The distribution coefficient (D7.4) values of the prodrugs 5a-d, 6a-d and the parent drugs 1a-d in an n-octanol/phosphate buffer (pH =7.4) system indicated enhanced lipophilic properties of the prodrugs. Furthermore, the HMIS ester prodrugs 6a-d are more lipophilic than the corresponding HMSI derivatives 5a-d. In vivo ulcerogenicity studies using scanning electron microscopy on stomach specimens of rats treated with an oral dose for 4 d revealed that the synthesized ester prodrugs are significantly less irritating to gastric mucosa than the parent drugs. These results suggested HMSI and/or HMIS esters possess good potential as prodrugs with an improved therapeutic index for oral delivery of NSAIDs.