Tetrahydroharmine

Base Information

• Chemical Name: Tetrahydroharmine
• CAS No.: 17019-01-1
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.283
• NSC Number: 99788
• UNII: F1Q1E0G45A
• DSSTox Substance ID: DTXSID70901873
• Nikkaji Number: J512.276G
• Wikipedia: Tetrahydroharmine
• Wikidata: Q135068
• ChEMBL ID: CHEMBL129208
• Mol file: 17019-01-1.mol

Synonyms:1,2,3,4-tetrahydroharmine;tetrahydroharmine

Chemical Property of Tetrahydroharmine

Chemical Property:

• Vapor Pressure: 1.4E-06mmHg at 25°C
• Melting Point: 199 °C
• Boiling Point: 399.2°Cat760mmHg
• PKA: 18.03±0.40(Predicted)
• Flash Point: 195.2°C
• PSA: 37.05000
• Density: 1.145g/cm³
• LogP: 2.71200
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 216.126263138
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

98%, ^*data from raw suppliers

Tetrahydroharmine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC
• Description: This carboline alkaloid is present in Banisteria caapi, a plant indigenous toSouth America. It is dextrorotatory with [o:]l>s + 32° (c 1.0, CHCI3). One methoxyl group, a methyl group and two imino groups are present in the molecule.
• Uses: Tetrahydroharmine is a β-Carboline derivative. β-Carboline alkaloids are inhibitors of human monoamine oxidase enzymes. β-carboline derivatives were also reported to have antiviral and fungicidal activity. Tetrahydroharmine is related to 3,4-Dihydroharmine (D449718).

Technology Process of Tetrahydroharmine

There total 10 articles about Tetrahydroharmine 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: 99.3%

harmaline (304-21-2) → tetrahydroharmine (486-93-1,17019-01-1)

Guidance literature:

With F₆P^(1-)*C₂₀H₃₆IrN₆P₂⁽¹⁺⁾; hydrogen; In water; at 80 ℃; for 25h; under 15001.5 Torr; Reagent/catalyst; Time; Catalytic behavior; Autoclave; Green chemistry;

DOI:10.1039/c2gc36144b

Reference yield: 96.0%

Harmaline hydrochloride (6027-98-1) → tetrahydroharmine (486-93-1,17019-01-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; isopropyl alcohol; at 0 ℃; for 1h;

DOI:10.1002/hlca.19860690620

Reference yield: 92.0%

acetaldehyde (75-07-0,9002-91-9) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → tetrahydroharmine (486-93-1,17019-01-1)

Guidance literature:

With hydrogenchloride; In water; at 40 ℃; for 6h;

DOI:10.1016/j.bmcl.2016.06.087

upstream raw materials:

harmine

harmaline

acetaldehyde

2-(6-methoxy-1H-indol-3-yl)ethanamine

Downstream raw materials:

harmine

(1S)-2-<((R)-1-phenylethyl)carbamoyl>-1,2,3,4-tetrahydroharmine

4-acetyltetrahydroharmine

Refernces

• 1、 Du, Hongtao,Tian, Shan,Chen, Juncheng,Gu, Hongling,Li, Na,Wang, Junru. "Synthesis and biological evaluation of N9-substituted harmine derivatives as potential anticancer agents". . p. 4015 - 4019. Retrieved 2016.
• 2、 Dell'Anna, Maria Michela,Capodiferro, Vito Filippo,Mali, Matilda,Manno, Daniela,Cotugno, Pietro,Monopoli, Antonio,Mastrorilli, Piero. "Highly selective hydrogenation of quinolines promoted by recyclable polymer supported palladium nanoparticles under mild conditions in aqueous medium". . p. 89 - 95. Retrieved 2014.
• 3、 Huang, Yuan-Qiong,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min. "Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer". supporting information. p. 2065 - 2069. Retrieved 2018/01/27.
• 4、 -. "?-CARBOLINE, DIHYDRO-?-CARBOLINE AND TETRAHYDRO-?-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES". . . Retrieved 2016/11/28.