73816-50-9

Usage

Chemical class

Quaternary ammonium salt

Derivation

Derived from an indole compound and a methoxybenzyl amine

Pharmaceutical potential

Has potential pharmaceutical properties

Possible applications

May have applications in medicinal chemistry, particularly in the development of drugs targeting the central nervous system or other biological systems

Biological interactions

May have interactions with biological macromolecules such as proteins or nucleic acids

Value in research

May be a valuable tool in both research and drug discovery

Further studies needed

Further studies are needed to fully understand the potential uses and effects of 2-(1H-indol-3-yl)-N-(4-methoxybenzyl)ethanaminium chloride.

Upstream product

• 61-54-1 tryptamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 93879-05-1 tryptamine 

Relevant academic research and scientific papers

ANTI-INFECTIVE HETEROCYCLIC COMPOUNDS AND USES THEREOF

The present invention relates to heterocyclic compounds of Formula F-I useful as anti-infective agents. The present invention further relates to a method of treating an infection by administering such compounds, and to pharmaceutical compositions comprising such compounds.

5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines

The last fifteen years have seen the emergence and overflow into the drug scene of “superpotent” N-benzylated phenethylamines belonging to the “NBOMe” series, accompanied by numerous research articles. Although N-benzyl substitution of 5-methoxytryptamine is known to increase its affinity and potency at 5-HT2 receptors associated with psychedelic activity, N-benzylated tryptamines have been studied much less than their phenethylamine analogs. To further our knowledge of the activity of N-benzyltryptamines, we have synthesized a family of tryptamine derivatives and, for comparison, a few 5-methoxytryptamine analogs with many different substitution patterns on the benzyl moiety, and subjected them to in vitro affinity and functional activity assays vs. the human 5-HT2 receptor subtypes. In the binding (radioligand displacement) studies some of these compounds exhibited only modest selectivity for either 5-HT2A or 5-HT2C receptors suggesting that a few of them, with affinities in the 10–100 nanomolar range for 5-HT2A receptors, might presumably be psychedelic. Unexpectedly, their functional (calcium mobilization) assays reflected very different trends. All of these compounds proved to be 5-HT2C receptor full agonists while most of them showed low efficacy at the 5-HT2A subtype. Furthermore, several showed moderate-to-strong preferences for activation of the 5-HT2C subtype at nanomolar concentrations. Thus, although some N-benzyltryptamines might be abuse-liable, others might represent new leads for the development of therapeutics for weight loss, erectile dysfunction, drug abuse, or schizophrenia.