78263-90-8

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-5-HYDROXYTRYPTAMINE is used as a pharmaceutical agent for its agonistic effects on the 5-HT3 receptor. Its interaction with this receptor makes it a potential candidate for the development of drugs targeting various neurological and psychiatric disorders, such as anxiety, depression, and migraines.
Used in Research and Development:
In the field of research and development, 2-METHYL-5-HYDROXYTRYPTAMINE serves as an important compound for studying the role of serotonin and its receptors in the central nervous system. It can be used to investigate the mechanisms of action of various drugs, as well as to develop new therapeutic strategies for treating serotonin-related conditions.
Used in Neurochemical Studies:
2-METHYL-5-HYDROXYTRYPTAMINE is used as a research tool in neurochemical studies to understand the role of serotonin in the brain and its involvement in various physiological processes. This knowledge can contribute to the development of novel treatments for neurological disorders and improve our understanding of the complex interactions between neurotransmitters and their receptors.

InChI:InChI=1/C11H14N2O/c1-7-9(4-5-12)10-6-8(14)2-3-11(10)13-7/h2-3,6,13-14H,4-5,12H2,1H3

Upstream product

• 28089-03-4 2-(5-methoxy-2-methyl-1H-indol-3-yl)ethan-1-amine hydrochloride 
• 93654-26-3 (5-benzyloxy-2-methyl-indol-3-yl)-oxo-acetyl chloride 
• 3143-97-3 2-(5-methoxy-2-methyl-1H-indol-3-yl)ethanamine 
• 1292285-89-2 C₁₁H₁₂N₂O₃ 
• 23210-18-6 5-methoxy-2-methyl-3-(2-nitro-ethyl)-indole 
• 33297-04-0 3-(2-nitrovinyl)-5-methoxy-2-methyl-1H-indole 
• 6260-86-2 5-methoxy-2-methyl-1H-indole-3-carbaldehyde 
• 1076-74-0 5-methoxy-2-methyl-1H-indole 
• 124224-50-6 5-benzyloxy-2-methyl-indole 
• 18658-09-8 2-(5-(benzyloxy)-2-methyl-1H-indol-3-yl)ethylamine 

Relevant academic research and scientific papers

Pharmacological assessment of sepiapterin reductase inhibition on tactile response in the rat

There is an unmet medical need for nonopioid pain therapies in human populations; several pathways are under investigation for possible therapeutic intervention. Tetrahydrobiopterin (BH4) has received attention recently as a mediator of neuropathic pain. Recent reports have implicated sepiapterin reductase (SPR) in this pain pathway as a regulator of BH4 production. To evaluate the role of SPR inhibition on BH4 reduction, we developed analytical methods to monitor the relationship between the plasma concentration of test article and endogenous pterins and applied these in the rat spinal nerve ligation pain model. Sepiapterin is an endogenous substrate, which accumulates upon inhibition of SPR. In response to a potent inhibitor of SPR, plasma concentrations of sepiapterin increased proportionally with exposure. An indirect-effect pharmacokinetic/pharmacodynamic model was developed to describe the relationship between the plasma pharmacokinetics of test article and plasma sepiapterin levels in the rat, which was used to determine an in vivo SPR IC50 value. SPR inhibition and mechanical allodynia were assessed coordinately with pterin biomarkers in plasma and at the site of neuronal injury (i.e., dorsal root ganglion). Upon daily oral administration for 3 consecutive days, unbound plasma concentrations of test article exceeded the unbound in vivo rat SPR IC90 throughout the dose intervals, leading to a 60% reduction in BH4 in the dorsal root ganglion. Despite evidence for pharmacological modulation of the BH4 pathway, there was no significant effect on the tactile paw withdrawal threshold relative to vehicle-treated controls.

Structural Characterization and Computer-Aided Optimization of a Small-Molecule Inhibitor of the Arp2/3 Complex, a Key Regulator of the Actin Cytoskeleton

CK-666 (1) is a recently discovered small-molecule inhibitor of the actin-related protein 2/3 (Arp2/3) complex, a key actin cytoskeleton regulator with roles in bacterial pathogenesis and cancer cell motility. Although 1 is commercially available, the crystal structure of Arp2/3 complex with 1 bound has not been reported, making its mechanism of action uncertain. Furthermore, its relatively low potency increases its potential for off-target effects invivo, complicating interpretation of its influence in cell biological studies and precluding its clinical use. Herein we report the crystal structure of 1 bound to Arp2/3 complex, which reveals that 1 binds between the Arp2 and Arp3 subunits to stabilize the inactive conformation of the complex. Based on the crystal structure, we used computational docking and free-energy perturbation calculations of monosubstituted derivatives of 1 to guide optimization efforts. Biochemical assays of ten newly synthesized compounds led to the identification of compound 2, which exhibits a threefold increase in inhibitory activity invitro relative to 1. In addition, our computational analyses unveiled a surface groove at the interface of the Arp2 and Arp3 subunits that can be exploited for additional structure-based optimization.

SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN

Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and pro-drugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain)

5-HT1 and 5-HT2 binding profiles of the serotonergic agents alpha-methylserotonin and 2-methylserotonin.

alpha-Methyl-5-hydroxytryptamine (alpha-Me-5-HT; 2) and 2-methyl-5-hydroxytryptamine (2-Me-5-HT; 3) are considered to be 5-HT2-selective and 5-HT3-selective agents, respectively. These agents were synthesized and examined at serotonin (5-HT) binding sites