23580-89-4

Basic information

• Product Name: METHYL-(3-PHENYL-PROPYL)-AMINE
• Synonyms: TIMTEC-BB SBB010169;METHYL-(3-PHENYL-PROPYL)-AMINE;(3-PHENYLPROPYL)METHYLAMINE;N-Methyl-3-phenylpropylamine;Fluoxetine Related Compound B (5 mL of a 0.01N HCl solution, approx. 2 mg/mL) (N- methyl-3-phenylpropylamine);Fluoxetine Related CoMpound B;N-Methyl-3-phenylpropan-1-aMine;N-(3-Phenylpropyl)methylamine
• CAS NO: 23580-89-4
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 23580-89-4.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 227℃
• Flash Point: 98℃
• Appearance: /
• Density: 0.909
• Vapor Pressure: 0.0779mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 10.60±0.10(Predicted)
• BRN: 2354870
• CAS DataBase Reference: METHYL-(3-PHENYL-PROPYL)-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-(3-PHENYL-PROPYL)-AMINE(23580-89-4)
• EPA Substance Registry System: METHYL-(3-PHENYL-PROPYL)-AMINE(23580-89-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 23580-89-4(Hazardous Substances Data)

Usage

Description

METHYL-(3-PHENYL-PROPYL)-AMINE, also known as N-Methyl-3-phenylpropylamine, is a chemical compound that is identified as an impurity in the pharmaceutical drug Fluoxetine. It is characterized by its molecular structure, which consists of a methyl group attached to a 3-phenylpropylamine backbone. METHYL-(3-PHENYL-PROPYL)-AMINE is relevant in the context of pharmaceutical manufacturing and quality control.
Source:
METHYL-(3-PHENYL-PROPYL)-AMINE is typically found as an impurity in the synthesis or production process of Fluoxetine, a widely prescribed antidepressant medication.
Production Methods:
The production of METHYL-(3-PHENYL-PROPYL)-AMINE is not explicitly detailed in the provided materials. However, it is understood that this compound is a byproduct or impurity in the synthesis of Fluoxetine, which is manufactured through a series of chemical reactions.

Uses

Used in Pharmaceutical Quality Control:
METHYL-(3-PHENYL-PROPYL)-AMINE is used as a reference standard for the identification and quantification of impurities in Fluoxetine (F597100). The presence of this compound in Fluoxetine is monitored to ensure the quality, safety, and efficacy of the final drug product.
Used in Research and Development:
In the pharmaceutical industry, METHYL-(3-PHENYL-PROPYL)-AMINE serves as a research compound for the development of new drugs and the improvement of existing ones. Understanding the properties and effects of this compound can contribute to the advancement of pharmaceutical science and the creation of more effective treatments for various conditions.
Used in Regulatory Compliance:
METHYL-(3-PHENYL-PROPYL)-AMINE is used as a benchmark in the regulatory compliance process for the drug Fluoxetine. Regulatory agencies require the identification and control of impurities to ensure that the drug meets safety and efficacy standards before it can be approved for use in the general population.

InChI:InChI=1/C10H15N/c1-11-9-5-8-10-6-3-2-4-7-10/h2-4,6-7,11H,5,8-9H2,1H3

Upstream product

• 100-42-5 styrene 
• 51-80-9 bis-(dimethylamino)methane 
• 72037-46-8 1-methyl-4-phenyl-1-azabutadiene 
• 103275-33-8 [3-(3-chloro-phenyl)-propyl]-methyl-amine 
• 859941-65-4 methyl-(3-phenyl-propyl)-carbamonitrile 
• 501361-46-2 N-4-dimethyl-N-(3-phenylpropyl)benzenesulfonamide 
• 104-52-9 phenylpropyl chloride 
• 74-89-5 methylamine 
• 50-00-0 formaldehyd 
• 110-68-9 N-n-butyl-N-methylamine 
• 4747-21-1 N-methylpropan-2-amine 
• 2439-54-5 N-methyl-N-octylamine 
• 506-59-2 N,N-dimethylammonium chloride 
• 36627-00-6 N,N-dimethylaminomethyl iodide 

Downstream Products

• 37082-04-5 2-(methyl(3-phenylpropyl)amino)ethanol 
• 58929-48-9 Methyl-[2-(2-{2-[methyl-(3-phenyl-propyl)-amino]-ethoxy}-ethoxy)-ethyl]-(3-phenyl-propyl)-amine 
• 30457-88-6 2-benzyl-2-propenal 
• 93948-20-0 bis-(3-phenyl-propyl)-amine 
• 137074-93-2 (4-{2-[Methyl-(3-phenyl-propyl)-amino]-acetyl}-piperazin-1-yl)-pyridin-3-yl-acetonitrile 
• 111633-10-4 {(R)-1-[Methyl-(3-phenyl-propyl)-carbamoyl]-ethyl}-carbamic acid benzyl ester 
• 133228-99-6 1-[Methyl-(3-phenyl-propyl)-amino]-3-(4-nitro-phenoxy)-propan-2-ol 
• 61930-99-2 N-Methyl-N-(3-phenyl-propyl)-β-phenyl-propionamid 
• 202810-99-9 N-methyl-N-((1R)-1-(N-methyl-N-(3-phenylpropyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamic acid tert-butyl ester 
• 847776-62-9 C₂₈H₃₅N₃O₂ 

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.

Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides

The first continuous flow process was developed to synthesize N-methyl secondary amines from alkyl mesylates and epoxides via a nucleophilic substitution using aqueous methylamine. A variety of N-methyl secondary amines were produced in good to excellent yields, including a number of bioactive compounds or their precursors. Up to 10.6 g (88% yield) of an N-methyl secondary amine was produced in 140 min process time. The amination procedure included an in-line workup, and the starting mesylate material was also produced in continuous flow from the corresponding alcohol. Finally, an in-line process combining the mesylate synthesis and nucleophilic substitution was developed.

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.