138113-09-4

Basic information

• Product Name: 2-(7-METHOXYNAPHTHALEN-1-YL)ETHANAMINE
• Synonyms: 2-(7-METHOXYNAPHTHALEN-1-YL)ETHANAMINE;2-(7-Methoxy-1-naphthyl)ethanamine;2-(7-Methoxynaphthalen-1-yl)ethylaMine;7-Methoxy-1-naphthaleneethanaMine;2-(7-METHOXYPHTHALEN-1-YL)ETHAMINE;Agomelatine intermediate;2-(7-Methoxynaphth-1-yl)ethylamine
• CAS NO: 138113-09-4
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.27
• EINECS: 1312995-182-4
• Mol File: 138113-09-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 353.567 °C at 760 mmHg
• Flash Point: 175.306 °C
• Appearance: /
• Density: 1.093
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: 2-8°C
• PKA: 9.73±0.10(Predicted)
• CAS DataBase Reference: 2-(7-METHOXYNAPHTHALEN-1-YL)ETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(7-METHOXYNAPHTHALEN-1-YL)ETHANAMINE(138113-09-4)
• EPA Substance Registry System: 2-(7-METHOXYNAPHTHALEN-1-YL)ETHANAMINE(138113-09-4)

Safety Data

• Hazardous Substances Data: 138113-09-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(7-Methoxynaphthalen-1-yl)ethanamine is used as a key intermediate in the synthesis of various pharmaceuticals for its aromatic properties and potential pharmacological effects.
Used in Organic Compounds Synthesis:
2-(7-Methoxynaphthalen-1-yl)ethanamine is used as a building block in the synthesis of various organic compounds, contributing to the development of new chemical entities with potential applications in different industries.
Used in Medical Research:
2-(7-Methoxynaphthalen-1-yl)ethanamine is used as a research tool in medical research to explore its potential pharmacological effects and applications in drug development.
Used in Drug Development:
2-(7-Methoxynaphthalen-1-yl)ethanamine is used in drug development as a starting material or a component in the formulation of new drugs, leveraging its aromatic properties and potential therapeutic effects.

InChI:InChI=1/C13H15NO/c1-15-12-6-5-10-3-2-4-11(7-8-14)13(10)9-12/h2-6,9H,7-8,14H2,1H3

Upstream product

• 1095930-99-6 7-methoxy-1-vinylnaphthalene 
• 5302-79-4 7-methoxynaphthalen-1-amine 
• 127299-26-7 (7-methoxy-3,4-dihydro-2H-naphthalene-1-ylidene)acetonitrile 
• 138112-76-2 agomelatine 
• 1424944-39-7 N-formyl-N-(2-(7-methoxynaphthalen-1-yl)ethyl)formamide 
• 185336-04-3 2-(7-methoxynaphthalen-1-yl)ethyl methanesulphonate 
• 99416-99-6 2-(7-methoxynaphthalen-1-yl)ethan-1-ol 
• 1523-11-1 naphthalen-2-yl acetate 
• 1424944-37-5 1-chloroacetyl-7-acetoxynaphthalene 
• 135-19-3 β-naphthol 
• 1424944-40-0 1-(2-nitroethyl)-7-methoxynaphthalene 
• 58150-14-4 1-(2-chloroethyl)-7-methoxynaphthalene 

Downstream Products

• 138112-76-2 agomelatine 
• 138112-99-9 N-[2-(7-Methoxynaphth-1-yl)Ethyl]-Butyramide 
• 1595280-05-9 1-(2-(7-methoxynaphthalen-1-yl)ethyl)-1H-pyrrole-2,5-dione 
• 1595280-04-8 1-(2-(7-methoxynaphthalen-1-yl)ethyl)-3,4-dimethyl-1H-pyrrole-2,5-dione 
• 1595280-07-1 3,4-dichloro-1-(2-(7-methoxynaphthalen-1-yl)ethyl)-1H-pyrrole-2,5-dione 
• 138112-82-0 N-[2-(7-methoxynaphth-1-yl)ethyl]-4chlorobutyramide 
• 138112-77-3 S 20099 
• 138112-81-9 N-[2-(7-methoxynaphth-1-yl)ethyl]-(2-oxopyrrolidin-1-yl)acetamide 
• 139525-77-2 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride 
• 138113-13-0 N-[2-(7-methoxy-1-naphthyl)ethyl]cyclobutanecarboxamide 
• 138112-79-5 N-[2-(7-methoxy-1-naphthyl)ethyl]propionamide 

Relevant articles and documents

Evaluation of agomelatine stability under different stress conditions using an HPLC method with fluorescence detection: application to the analysis of tablets and human plasma

A simple and highly sensitive stability-indicating HPLC method was developed and validated for the determination of the new antidepressant agent, agomelatine (AGM). Separation of AGM from its stress-induced degradation products was achieved on a BDS Hypersil phenyl column (250 mm × 4.6 mm i.d., 5 μm particle size) using methanol–0.05 M phosphate buffer of pH 2.5 (35: 65, v/v) as a mobile phase with fluorescence detection at 230/370 nm. Naproxen was used as an internal standard. The method satisfied all the validation requirements, as evidenced by good linearity (correlation coefficient of 0.9999, over the concentration range 0.4–40.0 ng/mL), accuracy (recovery average 99.55 ± 0.90%), precision (intra-day RSD 0.54–1.35% and inter-day RSD 0.93–1.26%), robustness and specificity. The stability of AGM was investigated under different ICH recommended stress conditions including acidic, alkaline, neutral, oxidative and photolytic. AGM was found to be labile to acidic and alkaline degradation and a kinetic study was conducted to explore its degradation behavior. First-order degradation rate constants and half-life times were calculated in each case. The proposed method was applied for the determination of AGM in tablets and spiked human plasma with mean percentage recoveries of 99.87 ± 0.31 (n = 3) and 102.09 ± 5.01 (n = 5), respectively. Hence, the proposed method was successfully applied for the determination of AGM in human volunteer plasma. The results were compared statistically with those obtained by a comparison HPLC method revealing no significant differences between the two methods regarding accuracy and precision. Copyright

New synthesis and purification method of agomelatine

The invention discloses a new method for synthesizing crystal form II agomelatine. The method comprises the following steps: performing reaction on a compound (I) serving as a raw material and hydrogen in an ammonia gas/ethanol system to obtain a compound (II); and performing reaction on a compound (II) and acetic anhydride in a sodium acetate/ethanol system to obtain a compound (III) crude product, and recrystallizing an absolute ethanol/ethyl acetate system to obtain the crystal form II agomelatine. The invention discloses a method (two-step method) for synthesizing the crystal form II agomelatine. The method is simple and safe in experimental condition, energy-saving, environment-friendly and simple in aftertreatment, the product is easily available, high in yield and high in purity, and the method is simple in process cost and suitable for industrialized mass production.

A compound and its preparation method and application

The invention provides a 1-cyan-1-(7-methoxyl-3, 4-dihdyro-1-naphthyl) methanol ester compound shown as a structural formula I described in the specification, wherein R is H, C1-C6 aliphatic groups or aryl. The invention further provides a preparation method of the compound and an application thereof in preparing agomelatine. The method of synthesizing agomelatine by the 1-cyan-1-(7-methoxyl-3, 4-dihdyro-1-naphthyl) methanol ester compound shown as the structural formula I is mild in condition, lower in production cost, higher in yield and fewer in impurities in end-products of reaction, and is more suitable for industrialized production.

Synthesis method of Agomelatine

The invention relates to a preparation method of Agomelatine. The preparation method is characterized by comprising the following steps: halogenating 7-methoxy-naphthylamine, performing potassium vinyltrifluoroborate substituting and ammonifying and protecting acetyl, so as to obtain a product. The preparation method has the advantages of being easily available in raw materials, concise in processes, high in total yield, less in by-products and simple in aftertreatment, therefore, the preparation method is suitable for industrial production.

Preparation method of agomelatine

The invention discloses a preparation method of agomelatine. In the method, 1-methyl-7-methoxynaphthalene is used as an initial raw material and is successively subjected to a bromination reaction with N-bromosuccinimide, a substitution reaction with nitromethane, a nitro-reduction reaction, and an acetylation reaction to produce a final product of agomelatine. The preparation method has fewer steps and employs low-cost and easy-to-obtained raw materials. During the reactions, high-risk and high-cost hydrogenation catalysts, such as palladium-carbon and Raney nickel, are not employed, so that the reactions are more reliable and require lower energy. The method can reduce transfer loss of intermediates, is simpler in operation, occupies fewer operators, is stable in product quality and high in yield and is suitable for large-scale industrial stable production.

1-CYAN-1-(7-METHOXYL-1-NAPHTYL) METHANOL ESTER COMPOUND AND PREPARATION METHOD AND USE THEREOF

Provided are a 1-cyan-1-(7-methoxyl-1-naphtyl) methanol ester compound, and preparation method and use thereof in the preparation of agomelatine intermediate 2-(7-methoxyl-1-naphtyl) ethylamine. Also provided is an agomelatine preparation method by using the 1-cyan-1-(7-methoxyl-1-naphtyl) methanol ester compound as an intermediate.

Novel difluoroacetamide analogues of agomelatine and melatonin: probing the melatonin receptors for MT1 selectivity

Synthesis and pharmacological evaluation of novel agomelatine and melatonin analogues with structures combining the features generating MT1 selectivity, namely the bulky hydrophobic ether moiety and the difluoroacetamide group, is reported. The dimeric agomelatine analogue linked by a three methylene spacer displayed the best affinity (Ki = 1.2 nM) and selectivity (7-fold) toward MT1 receptors.

Synthesis and evaluation of amide side-chain modified Agomelatine analogues as potential antidepressant-like agents

In this work, nineteen analogues of Agomelatine were readily synthesized through structural modification of the acetamide side-chain starting from the key common intermediate 2-(7-methoxynaphthalen-1-yl) ethanamine (3), which was prepared from commerciall

Process for the preparation of agomelatine

Disclosed is a process for the synthesis of Agomelatine (1), N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide from ethyl 2-(7-methoxynaphthalen-1-yl)acetate (4). Said synthesis method is particularly advantageous compared with known procedures because it uses low-cost reagents under mild reaction conditions and allows the isolation of a product with excellent yields and quality.

Novel conformationally constrained analogues of agomelatine as new melatoninergic ligands

Novel conformationally restricted analogues of agomelatine were synthesized and pharmacologically evaluated at MT1 and MT2 melatoninergic receptors. Replacement of the N-Acetyl side chain of agomelatine by oxathiadiazole-2-oxide (compound 3), oxadiazole-5(4H)-one (compound 4), tetrazole (compound 5), oxazolidinone (compound 7a), pyrrolidinone (compound 7b), imidazolidinedione (compound 12), thiazole (compounds 13 and 14) and isoxazole moieties (compound 15) led to a decrease of the melatoninergic binding affinities, particularly at MT1. Compounds 7a and 7b exhibiting nanomolar affinity towards the MT2 receptors subtypes have shown the most interesting pharmacological results of this series with the appearance of a weak MT2-selectivity.