74377-46-1

Usage

Class

Phenethylamine

Chemical relation

Related to mescaline

Effects

Hallucinogenic, altered sensory perception, heightened emotions

Mechanism of action

Serotonin receptor agonist at 5-HT2A and 5-HT2C receptors

Recreational use

Euphoric and empathogenic properties

Adverse reactions

Anxiety, paranoia, hallucinogen persisting perception disorder (HPPD)

Legal status

Illegal in many countries, classified as a controlled substance

InChI:InChI=1/C10H11NO/c1-11-7-9-6-8-4-2-3-5-10(8)12-9/h2-6,11H,7H2,1H3

Upstream product

• 36754-60-6 2-(chloromethyl)-1-benzofuran 
• 64663-59-8 N-methylbenzofuran-2-carboxamide 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 41717-28-6 2-benzofuroyl chloride 
• 4265-16-1 2-formylbenzo[b]furan 
• 74-89-5 methylamine 

Downstream Products

• 136727-04-3 N-<4-<3-<(2-benzofuranylmethyl)methylamino>-2-hydroxypropoxy>phenyl>methanesulfonamide 

Relevant academic research and scientific papers

Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 μM, ～10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

A systematic exploration of the effects of flexibility and basicity on sigma (σ) receptor binding in a series of substituted diamines

The sigma-1 receptor (S1R) has attracted a great deal of attention as a prospective drug target due to its involvement in numerous neurological disorders and, more recently, for its therapeutic potential in neuropathic pain. As there was no crystal structure of this membrane-bound protein reported until 2016, ligand generation was driven by pharmacophore refinements to the general model suggested by Glennon and co-workers. The generalised S1R pharmacophore comprises a central region where a basic amino group is preferred, flanked by two hydrophobic groups. Guided by this pharmacophore, S1R ligands containing piperazines, piperazinones, and ethylenediamines have been developed. In the current work, we systematically deconstructed the piperazine core of a prototypic piperazine S1R ligand (vide infra) developed in our laboratories. Although we did not improve the affinity at the S1R compared to the lead, we identified several features important for affinity and selectivity. These included at least one basic nitrogen atom, conformational flexibility and, for S1R, a secondary or tertiary amine group proximal to the anisole. Furthermore, S2R selectivity can be tailored with functional group modifications of the N-atom proximal to the anisole.

FAB I INHIBITORS

Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

HETEROCYCLIC COMPOUNDS, METHODS OF MAKING THEM AND THEIR USE IN THERAPY

In part, the present invention is directed to antibacterial compounds of formula (I) wherein A is a bicyclic heteroaryl ring or a tricyclic ring and R2 is an heterocyclic residue; L is a bond, or L is alkyl, alkenyl or cycloalkyl.

N-quinolinyl alkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing class III antiarrhythmic activity

This invention relates to N-heteroalkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing anti-arrhythmic activity, to pharmaceutical compositions and to methods for production thereof.

Substituted benzimidazole derivatives possessing Class III antiarrhythmic activity

This invention relates to N-heteroalkyl-substituted 1-aryloxy-2-propanolamine and proplyamine derivatives possessing anti-arrhythmic activity, to pharmaceutical compositions and to method for production thereof.

Synthesis and Selective Class III Antiarrhythmic Activity of Novel N-Heteroaralkyl-Substituted 1-(Aryloxy)-2-propanolamine and Related Propylamine Derivatives

The synthesis and biological evaluation of a series of novel 1-(aryloxy)-2-propanolamines and several related deshydroxy analogues are described.Compounds 4-29 were prepared and investigated for their class III electrophysiological activity in isolated canine Purkinje fibers and in anesthetized open-chest dogs.None of these compounds showed any class I activity.On the basis of the in vitro data, structure-activity relationships for the series are discussed.Two compounds, N-propoxy>phenyl>methanesulfonamide (12, WAY-123,223) and N-phenoxy>propyl>amino>methyl>-6-quinolinyl>methanesulfonamide (24, WAY-125,971) were identified and characterized as potent and specific class III antiarrhythmic agents in vitro and in vivo.Compound 12 was found to be orally bioavailable, to produce large increases of ventricular fibrillation threshold (VFT), and, in some instances, to restore sinus rhythm from ventricular fibrillation in anesthetized open-chest dogs at a dose of 5 mg/kg (iv).The enantiomers of 12 (i.e., 13 and 14) were synthesized and were found to exhibit similar electrophysiological effects in the Purkinje fiber screen.Compound 24, a propylamine analogue with potency and efficacy comparable to those of UK-68798 (2) and E-4031 (3), was studied in voltage-clamp experiments (isolated cat myocytes) and was found to be a potent and specific blocker of the delayed rectifier potassium current (IK).