N-(Carbamoylmethyl)taurine
[CAS# 7365-82-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Sulfonic acid amino compound
• Name: N-(Carbamoylmethyl)taurine
• Synonyms: 2-[(2-Amino-2-oxoethyl)amino]ethanesulfonic acid; ACES
• Molecular Formula: C₄H₁₀N₂O₄S
• Molecular Weight: 182.19
• CAS Registry Number: 7365-82-4
• EC Number: 230-908-4
• SMILES: C(CS(=O)(=O)O)NCC(=O)N

Properties

• Solubility: 40 g/L (water 20 °C)
• Melting point: 275 °C (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

N-(Carbamoylmethyl)taurine is an organic compound with the molecular formula C4H10N2O3S. It belongs to a class of compounds known as taurine derivatives. Taurine is a naturally occurring sulfonic acid that plays an important role in many biological processes, including bile salt formation, osmoregulation, and regulation of calcium signaling. Modification of taurine to produce derivatives such as N-(Carbamoylmethyl)taurine aims to exploit its biological properties for various applications.

The synthesis of N-(Carbamoylmethyl)taurine can be traced back to efforts to develop taurine analogs with enhanced or targeted functionality. The compound is synthesized by the direct reaction of taurine and an appropriate carbamoylating agent such as urea or isocyanate. The reaction results in the introduction of a carbamoyl group (-CONH2) into the taurine molecule, yielding N-(Carbamoylmethyl)taurine. The discovery process involved optimizing the reaction conditions to maximize yield and purity, making the compound available for further studies and applications.

N-(Carbamoylmethyl)taurine has attracted much attention for its potential therapeutic applications. Its unique structure enables it to interact with biological systems in ways that pure taurine cannot. Due to its potential to regulate cardiac function and protect against oxidative stress, researchers have explored its use in the development of drugs to treat cardiovascular disease. In addition, it also shows good promise in neuroprotective treatments, which can alleviate epilepsy and neurodegenerative diseases, among others.

In biochemical studies, N-(carbamoylmethyl) taurine is a valuable tool for studying the physiological effects of taurine and its metabolic pathways. By using this derivative, scientists can better understand how modifications of the taurine molecule affect its biological activity. This insight can facilitate the development of new taurine-based compounds with specific therapeutic targets.

Given the role of taurine in human health, N-(carbamoylmethyl) taurine is being explored as an ingredient in health foods and dietary supplements. It is thought that this derivative may have greater benefits than taurine alone, such as increased bioavailability or more targeted effects on the body. These supplements can support cardiovascular health, improve athletic performance, and enhance cognitive function.

Similar to its use in human health, N-(carbamoylmethyl)taurine is being studied for use in veterinary medicine. It has the potential to be a dietary supplement for pets, especially for species that require taurine to stay healthy, such as cats. This compound could help prevent diseases associated with taurine deficiency, such as dilated cardiomyopathy and retinal degeneration.

References

2023. Influence of the Structure of Taurine N-Derivatives on Their Complexing Properties. Russian Journal of Inorganic Chemistry, 68(4).
DOI: 10.1134/s0036023623600247

2019. Desolvation of the substrate-binding protein TauA dictates ligand specificity for the alkanesulfonate ABC importer TauABC. The Biochemical journal, 476(21).
DOI: 10.1042/bcj20190779

1980. Free metal ion depletion by ""Good's"" buffers. II. N-(2-acetamido)-2-aminoethanesulfonic acid (ACESH): complexes with calcium(II), magnesium(II), manganese(II), cobalt(II), zinc(II), nickel(II), and copper(II). Analytical Biochemistry, 103(2).
DOI: 10.1016/0003-2697(80)90258-4