18865-38-8

Basic information

• Product Name: 2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE
• Synonyms: 2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE;AKOS BBS-00006731;GLYCINEXYLIDINE;glycinexylidide;2-Amino-2',6'-dimethylacetoanilide;GX;N-(2,6-Dimethylphenyl)-2-aminoacetamide;N-(2,6-Dimethylphenyl)glycinamide
• CAS NO: 18865-38-8
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.23
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 18865-38-8.mol

Chemical Properties

• Boiling Point: 323.5°Cat760mmHg
• Flash Point: 149.4°C
• Appearance: /
• Density: 1.122g/cm³
• Vapor Pressure: 0.000261mmHg at 25°C
• Storage Temp.: -20°C
• PKA: pKa 7.68(H2O,t = 25.0±0.2,I=0.00) (Uncertain)
• CAS DataBase Reference: 2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE(18865-38-8)
• EPA Substance Registry System: 2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE(18865-38-8)

Safety Data

• Hazard Codes: T
• Statements: 61
• Safety Statements: 53-45
• Hazardous Substances Data: 18865-38-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE is used as a metabolite for [application reason] in the pharmaceutical industry. Its role in the metabolism of Lidocaine makes it a valuable compound for understanding and assessing hepatic function, which is crucial in the development and evaluation of various drugs and their potential effects on liver health.
Used in Hepatic Function Assessment:
2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE is used as an indicator for assessing hepatic function. Its presence and levels in the body can provide insights into the liver's ability to metabolize drugs, particularly Lidocaine, and can be used to monitor liver health and the effectiveness of treatments targeting liver-related conditions.
Used in Research and Development:
In the field of research and development, 2-AMINO-N-(2,6-DIMETHYLPHENYL)ACETAMIDE is used as a compound for studying the metabolic pathways of Lidocaine and other related drugs. This knowledge can contribute to the development of new drugs with improved hepatic metabolism profiles, potentially reducing the risk of liver toxicity and enhancing the overall safety and efficacy of pharmaceutical treatments.

InChI:InChI=1/C10H14N2O/c1-7-4-3-5-8(2)10(7)12-9(13)6-11/h3-5H,6,11H2,1-2H3,(H,12,13)/p+1

Upstream product

• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 87-62-7 2,6-dimethylaniline 
• 137-58-6 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide 
• 7728-40-7 N-(2,6-dimethylphenyl)-2-ethylaminoacetamide 
• 79-04-9 chloroacetyl chloride 
• 119053-70-2 2-azido-N-(2,6-dimethyl-phenyl)-acetamide 
• 153407-40-0 (+/-)-2-(tert-butoxycarbonyl)-amino-N-[(2,6-dimethyl)phenyl]acetamide 
• 1131-01-7 2-chloro-N-(2,6-dimethylphenyl)acetamide 

Downstream Products

• 76210-94-1 N-(2,6-Dimethyl-phenyl)-2-(2-hydroxy-3-phenoxy-propylamino)-acetamide; hydrochloride 
• 93969-03-0 2-(2,2,5,5-tetramethyl-2,5-dihydro-3-pyrroline-3-carbonylamino)-N-(2,6-dimethyl-phenyl)-acetamide 
• 102132-43-4 C₁₉H₂₆N₃O₃ 
• 102132-47-8 C₁₉H₂₈N₃O₃ 
• 76196-35-5 N-(2,6-Dimethyl-phenyl)-2-(2-hydroxy-3-phenoxy-propylamino)-acetamide 
• 102132-29-6 2,2,5,5-Tetramethyl-pyrrolidine-3-carboxylic acid [(2,6-dimethyl-phenylcarbamoyl)-methyl]-amide 
• 78029-93-3 N-[(2,6-Dimethyl-phenylcarbamoyl)-methyl]-2-mercapto-propionamide 
• 851528-09-1 decadeutrolidocaine 
• 747411-49-0 N-(2-(2,6-dimethylphenylamino)-2-oxoethyl)benzamide 

Relevant articles and documents

Simultaneous quantitation of lidocaine and its four metabolites by high-performance liquid chromatography: Application to studies on in vitro and in vivo metabolism of lidocaine in rats

A convenient and sensitive high-performance liquid chromatographic assay for the simultaneous quantitation of lidocaine and its four metabolites has been developed. The samples containing lidocaine and its metabolites were eluted from a microparticulate octadecylsilane column using a mobile phase of 0.1 M phosphate buffer (pH 3.0) containing 10% acetonitrile. This method was applied to studies on in vitro metabolism and in vivo pharmacokinetics of lidocaine in rats. Kinetic studies of in vitro microsomal metabolism of lidocaine indicated that the apparent K(m) and V(max) for aromatic hydroxylation were smaller than those for N-deethylation. Lineweaver-Burk plots of the N-deethylation of lidocaine and those of its two primary metabolites indicated that at least two isozymes are taking part in these reactions. In in vivo lidocaine pharmacokinetics, the area under the blood concentration-time curve for the monodeethylated product, ω-ethylamino-2,6-dimethylacetanilide (1), varied considerably depending on the route of administration.

New isoleucine derived dipeptides as antiprotozoal agent: Synthesis, in silico and in vivo studies.

The increasing emergence of malaria drug-resistant parasites and the deficiency in effective chemotherapy for trypanosomiasis represents a huge challenge in infectious disease treatment in tropical regions. As regards to developing effective antiprotozoal agents, ten new ile-gly dipeptide sulphonamide derivatives were synthesized by condensing compound (10) with (8a-j)using peptide coupling reagents. Compounds11b, 11i and 11j were most potent in clearing Trypanosome brucei in mice with 11b showing comparable activity with diminazene aceturate. In the antimalarial study, 11b was the most active compound, even better than the standard. Molecular docking result suggests good interaction between the reported compounds and the target protein. The results of haematological analysis, liver and kidney function tests showed that the compounds had no adverse effect on the blood and organs. Compound 11b stands out amongst the derivatives haven shown better activity in both the antimalarial and antitrypanosomal assay.

Synthesis, molecular docking and antimalarial activity of phenylalanine-glycine dipeptide bearing sulphonamide moiety

Ten novel phenylalanine-glycine dipeptide sulphonamide conjugate were synthesized and characterized using 1HNMR, 13CNMR, FTIR and HRMS spectroscopic techniques. The in silico studies predicted better interactions of compounds with target protein residues and a higher dock score in comparison with standard drugs. The in vivo antimalarial study, hematological study, liver and kidney function test were evaluated on the synthesized compounds. Compounds 7h, 7i and 7j inhibited the parasite by 34.5–60.2% on day 4 of after-treatment exposure. Compound 7j inhibited the multiplication of the parasite by 60.2% on day 4 of after-treatment which was comparable with that of the standard drug with 68.8% inhibition at same day of after-treatment exposure.

Synthesis and anticonvulsant activity of some N-(benzoyl)glycinanilide derivatives

Glycine is a major inhibitory neurotransmitter and recent studies have shown that certain lipophilic glycine derivatives demonstrate anticonvulsant activity in animal epilepsy models. On the other hand, anilide is another fruitful structure for designing potential anticonvulsant agents. Ameltolide, ralitoline and some phthalimide derivatives are the examples of anilide analogs with potent anticonvulsant activity. In this study, two key structural pharmacophores were combined and a series of N-benzoylglycinanilide derivatives were designed. Their anticonvulsant activities evaluated against maximal electroshock (MES) and subcutaneous metrazole seizure tests, whereas their neurotoxicity was examined by rotarod test. The preliminary screening results indicated that majority of the compounds were effective in the MES test. None of the compounds showed neurotoxicity according to the rotarod test at studied doses. The most active compound in the series is N-(2-((4-methoxyphenyl)amino)- 2-oxoethyl)benzamide (compound 8) which bearing 4-methoxy substituent on the N-phenyl ring.

Preparation of human drug metabolites using fungal peroxygenases

The synthesis of hydroxylated and O- or N-dealkylated human drug metabolites (HDMs) via selective monooxygenation remains a challenging task for synthetic organic chemists. Here we report that aromatic peroxygenases (APOs; EC 1.11.2.1) secreted by the agaric fungi Agrocybe aegerita and Coprinellus radians catalyzed the H2O2-dependent selective monooxygenation of diverse drugs, including acetanilide, dextrorphan, ibuprofen, naproxen, phenacetin, sildenafil and tolbutamide. Reactions included the hydroxylation of aromatic rings and aliphatic side chains, as well as O- and N-dealkylations and exhibited different regioselectivities depending on the particular APO used. At best, desired HDMs were obtained in yields greater than 80% and with isomeric purities up to 99%. Oxidations of tolbutamide, acetanilide and carbamazepine in the presence of H218O2 resulted in almost complete incorporation of 18O into the corresponding products, thus establishing that these reactions are peroxygenations. The deethylation of phenacetin-d1 showed an observed intramolecular deuterium isotope effect [(kH/kD) obs] of 3.1 ± 0.2, which is consistent with the existence of a cytochrome P450-like intermediate in the reaction cycle of APOs. Our results indicate that fungal peroxygenases may be useful biocatalytic tools to prepare pharmacologically relevant drug metabolites.

FORMULATIONS OF N-OXIDE PRODRUGS OF LOCAL ANESTHETICS FOR THE TREATMENT OF PULMONARY INFLAMMATION ASSOCIATED WITH ASTHMA, BROCHITIS, AND COPD

A prodrug of lidocaine and related local anesthetic composition or formulation for delivery by aerosolization is described. The formulation containing an efficacious amount of lidocaine N-oxide prodrug or local anesthetic N-oxide prodrug able to inhibit i

SUBSTITUTED ACETANILIDES AND BENZAMIDES FOR THE TREATMENT OF ASTHMA AND PULMONARY INFLAMMATION

Substituted acetanilide or benzamide compositions or formulations for delivery by aerosolization are described. The formulation contains an efficacious amount of acetanilide or benzamide compound able to inhibit inflammation in asthmatic lungs. Compounds of the invention are formulated in 5 ml solution of a quarter normal saline having pH between 5.0 and 7.0. The method for treatment of respiratory tract inflammation by a formulation delivered as an aerosol having mass medium average diameter predominantly between 1 to 5 μ, produced by nebulization or dry powder inhaler.

Quantification of lidocaine and several metabolites utilizing chemical ionization mass spectrometry and stable isotope labeling

Quantification of the suspected metabolites of lidocaine in humans was carried out using the direct insertion probe and chemical-ionization mass spectrometry. Deuterated analogs of the metabolites of lidocaine were added to serial human plasma and urine s