2201-16-3

Basic information

• Product Name: N-methyl-1-phenylcyclohexanamine
• Synonyms: cyclohexanamine, N-methyl-1-phenyl-; N-Methyl-1-phenylcyclohexylamine
• CAS NO: 2201-16-3
• Molecular Formula: C₁₃H₁₉N
• Molecular Weight: 189.2967
• Mol File: 2201-16-3.mol

Chemical Properties

• Boiling Point: 284.1°C at 760 mmHg
• Flash Point: 126.3°C
• Density: 0.97g/cm³
• Vapor Pressure: 0.00303mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: N-methyl-1-phenylcyclohexanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-1-phenylcyclohexanamine(2201-16-3)
• EPA Substance Registry System: N-methyl-1-phenylcyclohexanamine(2201-16-3)

Safety Data

• Hazardous Substances Data: 2201-16-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-methyl-1-phenylcyclohexanamine is utilized as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its role as a potent dopamine reuptake inhibitor makes it a valuable tool in understanding the mechanisms of action related to stimulants and hallucinogens.
Used in Drug Development:
In the field of drug development, N-methyl-1-phenylcyclohexanamine serves as a lead compound for the creation of new medications targeting neurological disorders. Its ability to modulate dopamine levels could potentially be harnessed to develop treatments for conditions such as Parkinson's disease or attention deficit hyperactivity disorder (ADHD).
Used in Forensic Toxicology:
N-methyl-1-phenylcyclohexanamine is employed as a reference substance in forensic toxicology to aid in the identification and analysis of controlled substances in biological samples. This application is crucial for law enforcement and legal proceedings related to drug abuse and trafficking.

Upstream product

• 6289-40-3 1-(methylamino)cyclohexane-1-carbonitrile 
• 591-51-5 phenyllithium 
• 2201-26-5 1-Phenyl-cyclohexylisocyanat 
• 1135-67-7 1-phenyl-cyclohexanecarboxylic acid 
• 108-94-1 cyclohexanone 

Downstream Products

• 91281-23-1 N-allyl-N-methyl-1-phenylcyclohexylamine 

Relevant articles and documents

Palladium(II)-Catalyzed C(sp2)-H Carbonylation of Sterically Hindered Amines with Carbon Monoxide

A palladium-catalyzed, amine-directed C(sp2)-H carbonylation of α,α-disubstituted benzylamine under 1 atm of CO for the facile synthesis of sterically hindered benzolactam has been developed. The key to success is the use of 2,2,6,6-tetramethyl-1-piperidinyloxy as the crucial sole oxidant. The synthetic utility of this transformation has been demonstrated by the first concise synthesis of the natural product spiropachysin-20-one.

A Copper-Catalyzed Aerobic [1,3]-Nitrogen Shift through Nitrogen-Radical 4-exo-trig Cyclization

A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under an oxygen atmosphere (1 atm) has been developed for the construction of a diverse range of indole derivatives from α,α-disubstituted benzylamine. In this reaction, oxygen was used as a clean terminal oxidant, and water was produced as the only by-product. Five inert bonds were cleaved, and two C?N bonds and one C?C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application protential for the late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical onto a phenyl ring is involved in the catalytic cycle.

N-allyl analogues of phencyclidine: Chemical synthesis and pharmacological properties

Several N-allyl derivatives of 1-phenylcyclohexylamine (PCA) were prepared, and their pharmacology was briefly characterized. The mono- and diallyl derivatives 4-7 had phencyclidine-like activities in mice but were less potent behaviorally than phencyclidine (PCP). None were PCP antagonists. In vitro these compounds were competitive inhibitors of butyrylcholinesterase (BChE) and protected against inhibition by DFP. In addition, these agents displaced tritiated N-methyl-4-piperidyl benzilate from mouse-brain homogenates and inhibited the effects of acetylcholine on isolated guinea pig ileum. None of these in vitro effects correlated with their PCP-like behavioral activity in vivo in mice.