2436-04-6

Basic information

• Product Name: 7-METHOXYTRYPTAMINE
• Synonyms: 7-METHOXYTRYPTAMINE;3-(2-AMINOETHYL)-7-METHOXYINDOLE;2-(7-METHOXY-1H-INDOL-3-YL)-1-ETHANAMINE;3-(2-aminoethyl)-7-methoxy-indolhydrochloride;Ethanamine, 2-(7-methoxy-3-indolyl)-;7-METHOXYTRYPTAMINE free base;7-METHOXYTRYPTAMINE 98% (HPLC);2-(7-methoxy-1H-indol-3-yl)ethylammonium chloride
• CAS NO: 2436-04-6
• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24
• Product Categories: Tryptamines
• Mol File: 2436-04-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 135-136 °C
• Boiling Point: 380°C at 760 mmHg
• Flash Point: 183.6°C
• Appearance: /
• Density: 1.171±0.06 g/cm3(Predicted)
• Vapor Pressure: 5.61E-06mmHg at 25°C
• PKA: 16.69±0.30(Predicted)
• CAS DataBase Reference: 7-METHOXYTRYPTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHOXYTRYPTAMINE(2436-04-6)
• EPA Substance Registry System: 7-METHOXYTRYPTAMINE(2436-04-6)

Safety Data

• Hazardous Substances Data: 2436-04-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 23, p. 1689, 1993 DOI: 10.1080/00397919308011267

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

Upstream product

• 16990-42-4 7-methoxy-3-[(E)-2-nitrovinyl]-1H-indole 
• 96096-62-7 3-(2-nitroethyl)-7-methoxyindole 
• 18312-46-4 (2-methoxyphenyl)hydrazine 
• 3189-22-8 7-methoxy-1H-indole 
• 109021-64-9 8-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline 
• 96096-68-3 β-pyrrolidino-2-nitro-3-methoxystyrene 
• 109021-59-2 7-methoxy-1H-indole-3-carbaldehyde 
• 32464-55-4 2-(4,4-diethoxybutyl)isoindoline-1,3-dione 
• 16990-42-4 3-(2-nitrovinyl)-7-methoxy-1H-indole 
• 50656-47-8 7-methoxyindole-3-glyoxyl chloride 
• 148336-59-8 7-methoxyindole-3-glyoxylamide 

Downstream Products

• 96096-67-2 N-(benzyloxycarbonyl)-7-methoxytryptamine 
• 1132682-75-7 C₁₈H₁₈FN₃O₄ 
• 1631136-30-5 C₂₉H₃₂N₂O₂ 
• 125160-74-9 N-tosyl-7-methoxy-tryptamine 

Relevant articles and documents

Preparation of 7-methoxytryptamine

7-Methoxytryptamine (6a) was prepared from cheap and easily available starting materials by using the Abramovitch-Shapiro method

Alpha-ethyltryptamines as dual dopamine-serotonin releasers

The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2Areceptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2Areceptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential.

Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors

Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approximately 140,000 compounds identified the beta-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented.