Tetrahydroharman

Base Information

• Chemical Name: Tetrahydroharman
• CAS No.: 2506-10-7
• Molecular Formula: C12H14 N2
• Molecular Weight: 186.257
• European Community (EC) Number: 219-711-4
• NSC Number: 92525
• UNII: W6CLK26X7V
• DSSTox Substance ID: DTXSID901027440
• Nikkaji Number: J144.137J
• Wikipedia: Tetrahydroharman
• Wikidata: Q104399888
• Metabolomics Workbench ID: 134052
• ChEMBL ID: CHEMBL440524
• Mol file: 2506-10-7.mol

Synonyms:1-methyl-1,2,3,4-tetrahydro--beta-carboline;tetrahydroharman;tetrahydroharmane;tetrahydroharmane monohydrochloride;tetrahydroharmane, (+-)-isomer;tetrahydroharmane, (R)-isomer;tetrahydroharmane, (S)-isomer;tetrohydroharmane

Chemical Property of Tetrahydroharman

Chemical Property:

• Vapor Pressure: 1.91E-05mmHg at 25°C
• Melting Point: 179-180 °C
• Boiling Point: 362.6°Cat760mmHg
• PKA: 17.81±0.40(Predicted)
• Flash Point: 173.1°C
• PSA: 27.82000
• Density: 1.13g/cm³
• LogP: 2.70340
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 186.115698455
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

98%min ^*data from raw suppliers

Tetrahydroharman ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=C(CCN1)C3=CC=CC=C3N2
• General Description: 2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indole (tetrahydroharman) is a β-carboline alkaloid formed via the condensation of tryptamine and acetaldehyde, a reaction catalyzed by *Helicobacter pylori* in the presence of ethanol. It exhibits prototropic behavior in different pH environments, existing as dicationic, cationic, neutral, or anionic species with distinct fluorescence properties. Some β-carboline derivatives, including halogenated analogs, demonstrate neurotoxic effects by impairing dopamine metabolism and inhibiting mitochondrial respiration, though tetrahydroharman itself is less potent compared to highly halogenated variants. Additionally, structurally related tetrahydro-β-carbolines can be modified to produce acetylcholinesterase inhibitors, suggesting potential pharmacological relevance.

Technology Process of Tetrahydroharman

There total 63 articles about Tetrahydroharman 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: 93.0%

1-methyl-4,9-dihydro-3H-β-carboline (525-41-7) → eleagnine (2506-10-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 1h;

DOI:10.1021/ja4051235

Reference yield: 85.0%

tryptamine (61-54-1) + acetaldehyde (75-07-0,9002-91-9) → eleagnine (2506-10-7)

Guidance literature:

With toluene-4-sulfonic acid; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 24h; Inert atmosphere;

DOI:10.1002/jhet.3931

Reference yield: 80.0%

1-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-carboxylic acid (6543-83-5) → eleagnine (2506-10-7)

Guidance literature:

In hydrogenchloride; for 0.5h; Heating;

DOI:10.1021/jo01298a045

upstream raw materials:

harmane

1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester; hydrochloride

2,3-dimethyl-1,3-oxalidine

tryptamine

Downstream raw materials:

harmane

2-benzoyl-1-methyl-4-oxo-1,2,3,4-tetrahydro-β-carboline

(R)-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

(S)-(-)-tetrahydroharman