N-Acetyl-N-formyl-5-methoxykynurenamine

Base Information

• Chemical Name: N-Acetyl-N-formyl-5-methoxykynurenamine
• CAS No.: 52450-38-1
• Molecular Formula: C13H16N2O4
• Molecular Weight: 264.281
• Hs Code.: 2924299090
• European Community (EC) Number: 637-059-2
• NSC Number: 688263
• UNII: S82P8JZ4YJ
• DSSTox Substance ID: DTXSID90200451
• Nikkaji Number: J1.007.065A
• Wikidata: Q32039049
• Metabolomics Workbench ID: 38505
• ChEMBL ID: CHEMBL1882218
• Mol file: 52450-38-1.mol

Synonyms:AFMK;N-acetyl-N-formyl-5-methoxykynurenamine

Chemical Property of N-Acetyl-N-formyl-5-methoxykynurenamine

Chemical Property:

• Appearance/Colour: light brown solid
• Vapor Pressure: 7.17E-14mmHg at 25°C
• Melting Point: 138-140 °C
• Refractive Index: 1.56
• Boiling Point: 589.4 °C at 760 mmHg
• PKA: 13.79±0.70(Predicted)
• Flash Point: 310.3 °C
• PSA: 84.50000
• Density: 1.216 g/cm³
• LogP: 2.07220
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10 mg/mL
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 264.11100700
• Heavy Atom Count: 19
• Complexity: 333

Purity/Quality:

99% ^*data from raw suppliers

N-g-Acetyl-N-2-formyl-5-methoxykynurenamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NCCC(=O)C1=C(C=CC(=C1)OC)NC=O
• Description: Melatonin is a neurotransmitter widely distributed in eukaryotes and is closely linked to circadean rhythms in mammals including humans. AFMK is a melatonin metabolite first identified in rat brain. AFMK has antioxidant and free radical scavenging activities in several experimental models. AFMK may also be measured in plasma as an index of melatonin synthesis and metabolism.

Technology Process of N-Acetyl-N-formyl-5-methoxykynurenamine

There total 19 articles about N-Acetyl-N-formyl-5-methoxykynurenamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

formic acid (64-18-6) + tert-butyl (2-[3'-N-acetylaminopropargyl]-4-methoxyphenyl)carbamate (438580-16-6) → N1-acetyl-N2-formyl-5-methoxykynurenine (52450-38-1) + N-(3-(2-amino-5-methoxyphenyl)-3-oxopropyl)acetamide (52450-39-2)

Guidance literature:

With mercury(II) sulfate; In dichloromethane; water; at 42 ℃; for 4h;

DOI:10.1055/s-2002-20476

Reference yield: 55.0%

5-methoxy-N-acetyl-tryptamine (73-31-4) → N1-acetyl-N2-formyl-5-methoxykynurenine (52450-38-1)

Guidance literature:

With sodium periodate; In methanol; water; at 0 - 80 ℃; for 12h;

DOI:10.1016/j.ejmech.2020.112078

Reference yield: 48.0%

formic acid (64-18-6) + N-(3-(2-amino-5-methoxyphenyl)-3-oxopropyl)acetamide (52450-39-2) → N1-acetyl-N2-formyl-5-methoxykynurenine (52450-38-1)

Guidance literature:

for 3h; Reflux;

upstream raw materials:

formic acid

tert-butyl (2-[3'-N-acetylaminopropargyl]-4-methoxyphenyl)carbamate

carbon dioxide

5-methoxy-N-acetyl-tryptamine

Downstream raw materials:

N-(3-(2-amino-5-methoxyphenyl)-3-oxopropyl)acetamide

Refernces

• 1、 -. "Oxidative coupling rearrangement product based on tryptamine skeleton and preparation method and application thereof". Paragraph 0069-0077. . Retrieved 2021/09/01.
• 2、 Bolteau, Rapha?l,Descamps, Florian,Ettaoussi, Mohamed,Caignard, Daniel H.,Delagrange, Philippe,Melnyk, Patricia,Yous, Sa?d. "Quinazoline and phthalazine derivatives as novel melatonin receptor ligands analogues of agomelatine". . . Retrieved 2020/01/30.