5-Methoxy-N-methyltryptamine

Base Information

• Chemical Name: 5-Methoxy-N-methyltryptamine
• CAS No.: 2009-03-2
• Molecular Formula: C12H16N2O
• Molecular Weight: 204.272
• UNII: YBO217L5YV
• DSSTox Substance ID: DTXSID40173909
• Nikkaji Number: J41.061F
• Wikipedia: 5-MeO-NMT
• Wikidata: Q4639626
• Pharos Ligand ID: GRFL3T3J4H48
• Metabolomics Workbench ID: 66916
• ChEMBL ID: CHEMBL58579
• Mol file: 2009-03-2.mol

Synonyms:5-methoxy-alpha-methyltryptamine;5-methoxy-alpha-methyltryptamine dipicrate;5-methoxy-alpha-methyltryptamine hydrochloride;5-methoxy-alpha-methyltryptamine monohydrochloride, (+-)-isomer;5-methoxy-alpha-methyltryptamine, (+)-isomer;5-methoxy-alpha-methyltryptamine, (+-)-isomer;5-methoxy-alpha-methyltryptamine, (-)-isomer;5-methoxy-N-methyltryptamine;alpha,O-dimethylserotonin

Chemical Property of 5-Methoxy-N-methyltryptamine

Chemical Property:

• Vapor Pressure: 8.34E-06mmHg at 25°C
• Melting Point: >87°C (dec.)
• Boiling Point: 374.5°C at 760 mmHg
• Flash Point: 180.3°C
• Density: 1.11g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Sparingly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 204.126263138
• Heavy Atom Count: 15
• Complexity: 198

Purity/Quality:

99% ^*data from raw suppliers

N-Methyl-5-methoxytryptamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC1=CNC2=C1C=C(C=C2)OC
• Uses: 5-Methoxy-N-methyl-1H-Indole-3-ethanamine is a serotonin 5-HT2A receptor agonist.

Technology Process of 5-Methoxy-N-methyltryptamine

There total 20 articles about 5-Methoxy-N-methyltryptamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4) → 5-methoxy-N-methyltryptamine (2009-03-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1248/cpb.49.1159

Reference yield: 93.0%

5-methoxy-N-methoxycarbonyl-N-methyltryptamine (205384-47-0) → 5-methoxy-N-methyltryptamine (2009-03-2)

Guidance literature:

With sodium hydroxide; In methanol; Heating;

Reference yield: 71.0%

N-(2-(5-methoxy-1H-indol-3-yl)ethyl)formamide (104510-12-5) → 5-methoxy-N-methyltryptamine (2009-03-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 5h; Heating / reflux;

upstream raw materials:

N-[2-(5-methoxy-indol-3-yl)-ethyl]-N-methyl-toluene-4-sulfonamide

2-(5-methoxy-indol-3-yl)-N-methyl-2-oxo-acetamide

N-[2-(5-methoxy-1H-indol-3-yl)ethyl]benzyloxycarboxamide

5-methoxy-N-methoxycarbonyl-N-methyltryptamine

Downstream raw materials:

5-(4-bromobenzyloxy)-4-oxo-4H-chromene-2-carboxylic acid [2-(5-methoxy-1H-indol-3-yl)ethyl]methylamide

5-(4-bromobenzyloxy)-2-({[2-(5-methoxy-1H-indole-3-yl)ethyl]methylamino}methyl)-chromen-4-one

5-methoxy-N-methyl-N-isopropyltryptamine

Refernces

• 1、 Zhao, Guodong,Liang, Lixin,Wang, Eryu,Lou, Shaoyan,Qi, Rui,Tong, Rongbiao. "Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide". supporting information. p. 2300 - 2307. Retrieved 2021/04/12.
• 2、 Han, Hui,Xia, Ji-Bao,Yang, Shang-Dong. "Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones". . p. 3357 - 3369. Retrieved 2019/04/06.