38171-31-2

Basic information

• Product Name: [2-(4-CHLORO-PHENYL)-ETHYL]-METHYL-AMINE
• Synonyms: [2-(4-CHLORO-PHENYL)-ETHYL]-METHYL-AMINE;4-Chloro-N-Methyl-benzeneethanaMine;N-[2-(4-Chlorophenyl)ethyl]-N-methylamine;2-(4-chlorophenyl)-N-MethylethanaMine
• CAS NO: 38171-31-2
• Molecular Formula: C₉H₁₂ClN
• Molecular Weight: 169.65
• Mol File: 38171-31-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 237°C at 760 mmHg
• Flash Point: 97.1°C
• Appearance: /
• Density: 1.063g/cm³
• Vapor Pressure: 0.046mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: [2-(4-CHLORO-PHENYL)-ETHYL]-METHYL-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(4-CHLORO-PHENYL)-ETHYL]-METHYL-AMINE(38171-31-2)
• EPA Substance Registry System: [2-(4-CHLORO-PHENYL)-ETHYL]-METHYL-AMINE(38171-31-2)

Safety Data

• Hazardous Substances Data: 38171-31-2(Hazardous Substances Data)

Usage

Uses

N-Methyl-4-chlorophenethylamine is a useful reactant for organic reactions and synthesis.

InChI:InChI=1/C9H12ClN/c1-11-7-6-8-2-4-9(10)5-3-8/h2-5,11H,6-7H2,1H3

Upstream product

• 60336-41-6 2-(4-chlorophenyl)-N-methylacetamide 
• 167886-56-8 1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene 
• 328281-40-9 2-4-chlorophenylethylcarbamic acid methyl ester 

Downstream Products

• 1226103-88-3 2-chloro-N-[2-(4-chlorophenyl)ethyl]-N-methylacetamide 
• 1431697-94-7 (±)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 1103521-25-0 2-chloro-N-[2-(4-chlorophenyl)ethyl]-6,7-dimethoxy-N-methylquinazolin-4-amine 

Relevant articles and documents

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

INHIBITORS OF N-ACYLPHOSPHATIDYLETHANOLAMINE PHOSPHOLIPASE D (NAPE-PLD)

The invention relates to a compound of the formula (I) as novel inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD), and to use thereof for the prophylaxis or treatment of diseases associated with NAPE-PLD. wherein in a ring A, X1 is N, or CR4; X2 is N or CR5; X3 is N or CH; with the proviso that at least one of X1 and X3 is N.

Structure-activity correlations for β-phenethylamines at human trace amine receptor 1

A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of β-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemagglutinin-tagged hTAAR 1 was stably co-expressed with rat Gαs. Analogs with multiple substituents as well as analogs with bulky groups were found to be partial agonists. Analogs in which the primary amino group was converted to a secondary or a tertiary amino group by N-methylation were also partial agonists. Comparative Molecular Field Analysis (CoMFA) using the potency data yielded a regression coefficient r2 of 0.824. The steric field contribution to the model was 61% with the balance (39%) contributed by the electrostatic field. The collective results suggest that increasing steric bulk both at the amino nitrogen, particularly by N-dimethylation, and at the 4-position of the aromatic ring leads to low efficacy ligands.