17019-01-1

Basic information

• Product Name: tetrahydroharmine
• Synonyms: tetrahydroharmine;Tetrahydroharmin;1,2,3,4-Tetrahydroharmine;1H-Pyrido(3,4-B)indole, 2,3,4,9-tetrahydro-7-methoxy-1-methyl- (van);7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• CAS NO: 17019-01-1
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.28
• Mol File: 17019-01-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 199 °C
• Boiling Point: 399.2°Cat760mmHg
• Flash Point: 195.2°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 1.4E-06mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• PKA: 18.03±0.40(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: tetrahydroharmine(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydroharmine(17019-01-1)
• EPA Substance Registry System: tetrahydroharmine(17019-01-1)

Safety Data

• Hazardous Substances Data: 17019-01-1(Hazardous Substances Data)

Usage

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).

References

Hochstein, Paradies., J. Arner. Chern. Soc., 79, 5735 (1957)Bernauer., Helv. Chirn. Acta, 47, 1075 (1960) Koblicova, Trojanek., Chern. Ind., 1342 (1966)

InChI:InChI=1/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3/t8-/m1/s1

Upstream product

• 6027-98-1 Harmaline hydrochloride 
• 57032-15-2 2-benzyl-7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 1229021-13-9 7-methoxy-2-benzyl-1-methyl-β-carbolinium bromide 
• 23084-35-7 2-(6-methoxy-1H-indol-3-yl)acetonitrile 
• 3189-13-7 6-methoxylindole 
• 105740-52-1 1-dibromomethyl-3,4-dihydro-7-methoxy-β-carboline 
• 75-07-0 acetaldehyde 
• 3610-36-4 2-(6-methoxy-1H-indol-3-yl)ethanamine 
• 304-21-2 harmaline 
• 442-51-3 harmine 

Downstream Products

• 17019-04-4 1-(7-methoxy-1-methyl-β-carbolin-9-yl)-1-phenylmethane 
• 17952-72-6 4-acetyltetrahydroharmine 
• 110691-55-9 (1S)-2-<((R)-1-phenylethyl)carbamoyl>-1,2,3,4-tetrahydroharmine 
• 442-51-3 harmine 

Relevant articles and documents

A polymer supported palladium(II) β-ketoesterate complex as active and recyclable pre-catalyst for selective reduction of quinolines in water with sodium borohydride Dedicated to the memory of Professor Benedetto Corain.

A polymer supported palladium catalyst, obtained by copolymerization of Pd(AAEMA)2 [AAEMA- = deprotonated form of 2-(acetoacetoxy) ethyl methacrylate] with ethyl methacrylate (co-monomer) and ethylene glycol dimethacrylate (cross-linker), exhibited excellent activity and selectivity for the hydrogenation of quinolines to 1,2,3,4-tetrahydroquinolines in the presence of NaBH4 as hydrogen donor in water. Both the activity and selectivity could be maintained for at least seven reaction runs. No metal leaching into solution occurred during recycles. TEM analyzes carried out on the catalyst showed that the active species were supported palladium nanoparticles having a mean size of 3 nm, which did not aggregate with the recycles.

Facile heterogeneous catalytic hydrogenations of C=N and C=O bonds in neat water: Anchoring of water-soluble metal complexes onto ion-exchange resins

Rare examples are known of non-covalent immobilization of water-soluble transition metal complexes onto solid supports and their application in catalytic hydrogenations in neat water. In the present work we report on the synthesis of a novel Ir(i) complex bearing the water soluble monodentate cage phosphine PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) and its immobilisation onto commercial ion-exchange resins by a straightforward heterogenization method. The materials obtained were used as catalysts for the hydrogenations of cyclic imines and α-keto esters under mild conditions using water as a green reaction medium, avoiding as much as possible the use of toxic and/or hazardous solvents.

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer

Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.

2 - substituted β - carbolines compound and its used for preparation for preventing or treating tumor drug application

The invention provides 2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors. The structural general formula of the compounds is disclosed as Formula I. The compounds have high inhibiting actions on growth of tumor cells, and have approximate activity to the positive control paclitaxel. Part of the compounds have obviously better antitumor activity than the paclitaxel; the IC50 value is less than 1 mu M; and thus, the compounds can become efficient drugs for treating tumors.