3761-48-6

Basic information

• Product Name: 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
• Synonyms: 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide;Einecs 223-177-8
• CAS NO: 3761-48-6
• Molecular Formula: C₁₄H₂₃N₃O₂
• Molecular Weight: 265.35132
• EINECS: 223-177-8
• Mol File: 3761-48-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 433.8°C at 760 mmHg
• Flash Point: 216.2°C
• Appearance: /
• Density: 1.079g/cm³
• Vapor Pressure: 9.95E-08mmHg at 25°C
• Refractive Index: 1.544
• PKA: 14.38±0.46(Predicted)
• CAS DataBase Reference: 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide(3761-48-6)
• EPA Substance Registry System: 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide(3761-48-6)

Safety Data

• Hazardous Substances Data: 3761-48-6(Hazardous Substances Data)

Usage

Description

4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide is a chemical compound with a complex structure that features an amino group, a diethylaminoethyl group, and a methoxybenzamide group. 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide is characterized by its potential applications in various fields, particularly in the medical and pharmaceutical industries.

Uses

Used in Pharmaceutical Industry:
4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide is used as a key intermediate in the synthesis of radioiodinated MIP-1145, which is a therapeutic agent for the treatment of melanoma. Melanoma is a type of skin cancer that can be aggressive and difficult to treat. 4-amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide plays a crucial role in the development of this targeted therapy, which aims to specifically address melanoma cells while minimizing damage to healthy tissues.

InChI:InChI=1/C14H23N3O2/c1-4-17(5-2)9-8-16-14(18)12-7-6-11(15)10-13(12)19-3/h6-7,10H,4-5,8-9,15H2,1-3H3,(H,16,18)

Upstream product

• 27492-84-8 Methyl 4-amino-2-methoxybenzoate 
• 100-36-7 N,N-diethylethylenediamine 
• 476615-23-3 N-(2-diethylamino-ethyl)-4-nitro-2-methoxybenzamide 
• 3614-38-8 4-acetamido-N-(2-(diethylamino)ethyl)-2-methoxybenzamide 
• 2486-80-8 4-amino-2-methoxybenzoic acid 
• 55304-05-7 4-acetylamino-2-methoxy-benzoic acid 
• 4093-29-2 methyl 4-(acetylamino)-o-anisate 
• 2597-56-0 4-nitro-o-anisic acid 
• 39787-83-2 2-methoxy-4-nitrobenzoyl chloride 

Downstream Products

• 102176-19-2 4-butylamino-2-methoxy-benzoic acid-(2-diethylamino-ethylamide) 
• 3614-38-8 4-acetamido-N-(2-(diethylamino)ethyl)-2-methoxybenzamide 
• 848771-79-9 N-(2-diethylamino-ethyl)-2-methoxy-4-methylamino-benzamide 
• 864462-59-9 N-(2-(diethylamino)ethyl)-2-methoxy-4-(mesylamino)benzamide 
• 947263-67-4 N-(2-(diethylamino)ethyl)-2-methoxy-4-(tosylamino)benzamide 
• 947263-66-3 4-acetylamino-N-(2-diethylamino-ethyl)-5-iodo-2-methoxy-benzamide 
• 617244-87-8 N-(2-diethylamino-1-methyl-ethyl)-2-methoxy-4-[3-(4-trifluoromethoxy-phenyl)-ureido]-benzamide 
• 617245-66-6 4-[3-(3-chloro-phenyl)-ureido]-N-(2-diethylamino-ethyl)-2-methoxy-benzamide 
• 864462-57-7 N-(2-diethylamino-ethyl)-4-(2-benzyloxy-acetylamino)-2-methoxy-benzamide 
• 864462-53-3 benzo[1,3]dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbamoyl)-5-methoxy-phenyl]-amide 
• 1214283-53-0 N-(2-diethylamino-ethyl)-4-(4-fluoro-benzamido)-2-methoxybenzamide 

Relevant articles and documents

Development of radiofluorinated nicotinamide/picolinamide derivatives as diagnostic probes for the detection of melanoma

Regarding the increased incidence and high mortality rate of malignant melanoma, practical early-detection methods are essential to improve patients’ clinical outcomes. In this study, we successfully prepared novel picolinamide–benzamide (18 F-FPABZA) and nicotinamide–benzamide (18 F-FNABZA) conjugates and determined their biological characteristics. The radiochemical yields of18 F-FPABZA and18 F-FNABZA were 26 ± 5% and 1 ± 0.5%, respectively.18 F-FPABZA was more lipophilic (log P = 1.48) than18 F-FNABZA (log P = 0.68). The cellular uptake of18 F-FPABZA in melanotic B16F10 cells was relatively higher than that of18 F-FNABZA at 15 min post-incubation. However, both radiotracers did not retain in amelanotic A375 cells. The tumor-to-muscle ratios of18 F-FPABZA-injected B16F10 tumor-bearing mice increased from 7.6 ± 0.4 at 15 min post-injection (p.i.) to 27.5 ± 16.6 at 3 h p.i., while those administered with18 F-FNABZA did not show a similarly dramatic increase throughout the experimental period. The results obtained from biodistribution studies were consistent with those derived from microPET imaging. This study demonstrated that18 F-FPABZA is a promising melanin-targeting positron emission tomography (PET) probe for melanotic melanoma.

Synthesis and evaluation of novel radioiodinated benzamides for malignant melanoma

The imaging potential of a series of [123I]benzamides was studied in mice bearing B16F0 melanoma tumors. Compound [123I]25 exhibited tumor uptake >8 %ID/g at 1 h, while that of [123I]14d and [123I]25 reached a maximum of 9-12 %ID/g at 6 h. Standardized uptake values of [123I]14d were higher than 100 between 24 and 72 h after injection. In haloperidol treated animals, the tumor uptake of [ 123I]14d was not significantly different to controls, while significant reduction of [123I]25 uptake was observed, supporting that [123I]14d uptake relates to melanin interaction, whereas part of the mechanism of [123I]25 uptake is related to its σ1-receptor affinity. Benzamides 14d and 25, which display rapid and high tumor uptake, appear to be promising imaging agents for melanoma detection, while 14d, which displays a long lasting and high melanoma/nontarget ratio, is more suitable for evaluation as a potential radiotherapeutic.

RADIOHALOGENATED BENZAMIDE DERIVATIVES AND THEIR USE IN TUMOR DIAGNOSIS AND TUMOR THERAPY

This invention relates to new radiohalogenated benzamide derivatives and their use in tumor diagnosis and tumor therapy. The radiohalogenated benzamide derivatives according to the invention exhibit novel and especially advantageous properties, in particular with respect to tumor concentration and retardation, liver concentration and blood accumulation. The radiation-therapy doses to be achieved in the tumor, compared to healthy body tissue, are advantageous for the compounds according to the invention.