6-Methoxyharmalan

Base Information

• Chemical Name: 6-Methoxyharmalan
• CAS No.: 3589-73-9
• Molecular Formula: C13H14 N2 O
• Molecular Weight: 214.267
• Hs Code.: 2933990090
• UNII: 43F45VJV8C
• DSSTox Substance ID: DTXSID80957306,DTXSID10901872
• Nikkaji Number: J8.174D
• Wikidata: Q27164697,Q27258644
• Pharos Ligand ID: 6GURX8W9Z97A
• Metabolomics Workbench ID: 131661
• ChEMBL ID: CHEMBL338115
• Mol file: 3589-73-9.mol

Synonyms:1-Me-6-MDHBC;1-methyl-6-methoxy-dihydro-beta-carboline

Chemical Property of 6-Methoxyharmalan

Chemical Property:

• Appearance/Colour: Yellow crystalline solid.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 208 - 209oC
• Boiling Point: 417.7°Cat760mmHg
• Flash Point: 206.4°C
• PSA: 37.38000
• Density: 1.25g/cm³
• LogP: 1.97720
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 214.110613074
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

99%, ^*data from raw suppliers

6-Methoxyharmalan crystalline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NCCC2=C1NC3=C2C=C(C=C3)OC
• Description: A carboline alkaloid, this base occurs in the stems and leaves of Virola cuspidata. The structure has been shown to be 3:4-dihydro-6-methoxy-l-methyl-iJ-carboline from spectroscopic evidence.
• Uses: 6-Methoxyharmalan is useful in the treatment of autophagy-associated disorders ? ;Reactant for preparation of TRPV1-dependent vasodilator1

Technology Process of 6-Methoxyharmalan

There total 4 articles about 6-Methoxyharmalan 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:

2-<1-<<2-(5-Methoxy-1H-indol-3-yl)ethyl>amino>ethylidene>cycloheptanone (107292-50-2) → methoxy-6-harmalan (3589-73-9) + cycloheptanone (502-42-1)

Guidance literature:

With hydrogenchloride; In chloroform; at 23 ℃; for 7h; Product distribution;

DOI:10.1002/jhet.5570220643

Reference yield:

1-methoxy-4-<<2-(5-methoxy-1H-indol-3-yl)ethyl>amino>-3-penten-2-one (86474-87-5) → Methoxyacetone (5878-19-3) + methoxy-6-harmalan (3589-73-9)

Guidance literature:

With hydrogenchloride; In chloroform; at 23 ℃; for 0.0666667h;

Reference yield:

2-<1-<<2-(5-Methoxy-1H-indol-3-yl)ethyl>amino>ethylidene>cyclohexanone (107292-46-6) → methoxy-6-harmalan (3589-73-9) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 23 ℃; overnight;

DOI:10.1002/jhet.5570220643

upstream raw materials:

2-<1-<<2-(5-Methoxy-1H-indol-3-yl)ethyl>amino>ethylidene>cyclopentanone

2-<1-<<2-(5-Methoxy-1H-indol-3-yl)ethyl>amino>ethylidene>cyclohexanone

1-methoxy-4-<<2-(5-methoxy-1H-indol-3-yl)ethyl>amino>-3-penten-2-one

2-<1-<<2-(5-Methoxy-1H-indol-3-yl)ethyl>amino>ethylidene>cycloheptanone

Downstream raw materials:

6-methoxyharman

3-(2-hydroxybenzoyl)-9-methoxy-12b-methyl-6,7,12,12b-tetrahydro-indolo[2,3-a]quinolizine-1-carbonitrile

3-(2-hydroxybenzoyl)-9-methoxy-12b-methyl-6,7,12,12b-tetrahydro-indolo[2,3-a]quinolizine-1-carboxylic acid methyl ester

Refernces

• 1、 Bobowski, George. "Synthesis of 1-Substituted-2,3,4,9-tetrahydro-(2-oxopropyl)-1H-pyridoindoles and their Base-catalyzed Rearrangements to N-ethyl>acetamides". . p. 267 - 272. Retrieved 2007/10/02.