712-09-4

Basic information

• Product Name: 5-METHOXYTRYPTOPHOL
• Synonyms: 5-methoxy-1h-indole-3-ethano;5-methoxy-1h-indole-3-ethanol;5-methoxy-indole-3-ethano;5-METHOXY-3-(2-HYDROXYETHYL)INDOLE;5-METHOXYINDOLE-3-ETHANOL;5-METHOXYTRYPTOPHOL;2-(5-METHOXY-1H-INDOL-3-YL)-1-ETHANOL;2-(5-methoxy-1H-indol-3-yl)ethanol
• CAS NO: 712-09-4
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• EINECS: 211-919-3
• Product Categories: Indoles and derivatives
• Mol File: 712-09-4.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 326.97°C (rough estimate)
• Flash Point: 192 °C
• Appearance: White to off white powder
• Density: 1.224
• Vapor Pressure: 6.55E-07mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.90±0.10(Predicted)
• CAS DataBase Reference: 5-METHOXYTRYPTOPHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYTRYPTOPHOL(712-09-4)
• EPA Substance Registry System: 5-METHOXYTRYPTOPHOL(712-09-4)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• RTECS: NL8513000
• HazardClass: IRRITANT
• Hazardous Substances Data: 712-09-4(Hazardous Substances Data)

Usage

Description

5-Methoxytryptophol (5-MTOH) is a naturally occurring indole compound that is produced by the pineal gland. It is a product of melatonin metabolism and has been found to exhibit biological activity. The levels of 5-MTOH in plasma follow a diurnal pattern in both rodents and humans.

Uses

Used in Bone Metabolism:
5-Methoxytryptophol plays a significant role in bone metabolism. It is used as an inhibitor of osteoclastogenesis, which is the process of bone resorption by osteoclasts, and as a promoter of osteoblast differentiation, which is the process of bone formation by osteoblasts. This dual action makes 5-MTOH a potential therapeutic agent for the treatment of bone-related disorders, such as osteoporosis and other metabolic bone diseases.

InChI:InChI=1/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 99988-56-4 methyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 2426-19-9 (5-methoxy-1H-indol-3-yl)oxoacetyl chloride 
• 14771-33-6 ethyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 2436-17-1 5-methoxyindole-3-acetonitrile 
• 250672-50-5 1-(tert-butyldimethylsilyl)-3-bromo-5-methoxy-1H-indole 
• 162710-95-4 1-(tert-Butyldimethylsilyl)-5-methoxyindole 
• 1006-94-6 5-methoxylindole 
• 3471-31-6 5-methoxy-1H-indole-3-acetic acid 
• 23304-48-5 (5-methoxy-1H-indol-3-yl)acetic acid methyl ester 
• 13436-46-9 2-ethoxytetrahydrofuran 
• 335451-45-1 1-(tert-Butyldimethylsilyl)-3-(2-hydroxyethyl)-5-methoxyindole 

Downstream Products

• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 
• 1000681-51-5 3-(2-chloroethyl)-5-methoxy-1H-3-indole 
• 1394160-97-4 5-m-tolyl-oxazole-4-carboxylic acid {1-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-1H-pyrazol-4-yl}-amide 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 94164-55-3 2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethanol 
• 22139-72-6 2-(5-methoxy-1H-indol-3-yl)ethanal 

Relevant articles and documents

Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

We disclose herein a Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.

AZEPINO-INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS

The present invention provides azepino-indoles and other heterocycles and methods of using the compounds for treating brain disorders.

Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Br?nsted Acid

We disclose a nickel/Br?nsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me3P)4NiH]N(SO2CF3)2 in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.