756500-61-5

Basic information

• Product Name: N,2-DiMethyl-benzeneethanaMine
• Synonyms: N,2-DiMethyl-benzeneethanaMine;N-[2-(2-Methylphenyl)ethyl]-N-methylamine
• CAS NO: 756500-61-5
• Molecular Formula: C10H15N
• Molecular Weight: 149.2328
• Mol File: 756500-61-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,2-DiMethyl-benzeneethanaMine(CAS DataBase Reference)
• NIST Chemistry Reference: N,2-DiMethyl-benzeneethanaMine(756500-61-5)
• EPA Substance Registry System: N,2-DiMethyl-benzeneethanaMine(756500-61-5)

Safety Data

• Hazardous Substances Data: 756500-61-5(Hazardous Substances Data)

Upstream product

• 16793-90-1 1-(2-bromoethyl)-2-methylbenzene 
• 74-89-5 methylamine 
• 147410-32-0 (2-o-tolylethyl)carbamic acid tert-butyl ester 
• 55755-16-3 2-methylphenethylamine 
• 644-36-0 o-methylphenylacetic acid 
• 10166-09-3 (o-tolyl)acetyl chloride 
• 909373-25-7 N-methyl-2-(o-tolyl)acetamide 
• 19819-98-8 2-o-tolylethanol 
• 932-31-0 ortho-tolylmagnesium bromide 

Downstream Products

• 1268150-18-0 2-cyano-N-methyl-N-(2-methylphenethyl)acetamide 

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.

α-Diazo-β-ketonitriles: Uniquely reactive substrates for arene and alkene cyclopropanation

An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor-acceptor- substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. α-Diazo-β-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the α-cyano-α-ketocyclopropane products are demonstrated to serve as substrates for SN2, SN2′, and aldehyde cycloaddition reactions.